Rudolphomycin and Rednose

Rudolphomycin is a antitumor antibiotic compound. It was named following a series of such molecules derived from 'bohemic acid' - which was given its name because the discoverer Dr Nettleton was an avid opera fan and called it after the Puccini opera La Bohème. Derivatives of this were then given names from characters in the opera, such as mussettamycin and marcellomycin, after Musetta and Marcello, and rudolphomycin after the character Rudolph. On degradation of rudolphomycin, a new sugar was obtained, which was christened 'rednose'. This rather silly name was probably allowed to stand since the paper was submitted on December 21st 1978, and the journal editor probably had the Yuletide spirit!

Thanks to Janet McBride for suggesting these Christmas-ey molecules. More info: J. Am. Chem. Soc. 101 (1979) 7041.

George and Bi-George

The story goes that when undergraduate James Carnahan achieved the synthesis of a new cage structure at Columbia University, he asked his supervisor Prof Katz to suggest a name for it. Since trivial names are often arbitrary, he suggested 'George'. When George was heated with a Rh catalyst, it dimerised to produce Bi-George!

Eurekamic Acid

Eureka! was supposedly the exclamation used by Archimedes when he found something interesting in his bath water. It means 'I have found it', and so when researchers at May and Baker discovered this acid, they felt it was such a 'Eureka moment' that they named the molecule after it.

Catherine

I don't know much about this molecule except that its name comes from the plant Catharanthus roseus. I'm surprised, though, that it's not wheel shaped...

Complicatic Acid

This molecule didn't get its name because it was complicated to make, rather from the plant Stereum complicatum from which it was isolated.

Ptelefolone

This molecule rings a bell...It gets its name from the hop tree Ptelea trifoliata, but I don't know much else about it.

Pterodactyladiene

This is a group of molecules that resemble the ancient flying reptiles. The R groups can be altered to give different sized 'heads' or 'tails'.

Thanks to Ewart Shaw for suggesting this molecule.

Miazole and Urazole

If you pronounce the 'a' as in 'cat', and the 'z' as an 's', then you get the classic chemistry joke: What's the difference between miazole and urazole? The size of the ring...
And shouldn't there be a 'herazole', a 'theirazole' and an 'ourazole' to get a complete bunch of azoles? Actually, the proper name for miazole is imidazol, but that spoils the joke a bit....

Thanks to Steve Stinson for suggesting these molecules.

Ethyl Lactate

This is another standard undergraduate chemistry joke, based around the fact that Ethyl sounds like a common female name. "How do you make Ethyl lactate...?" Other names involving "Ethyl" such as Ethyl palpitate, Ethyl fornicate and the spinster Ethyl celibate also make good jokes, but unfortunately the corresponding acids (palpitic, fornic and celibatic) are unknown. In a similar vein, is copper tartrate what's paid to policewomen who are impersonating prostitures?

Thanks to John Figueras for suggesting this molecule and to Suds Mixer for info about it, and Colin Metcalf and to Peter Rice for the ethyl celibate and tartrate jokes, respectively.

Cristane

So what's so amusing about cristane? Well, for the non-biologists amongst you, a 'crissum' is the name given to the anus of a bird! Tricyclo[5.3.0.0]decane, was nicknamed cristane since on the evening it was first discovered in Brown University, someone left the window open. A pigeon got into the lab overnight and did what pigeons do - all over the lab and equipment. The clean-up crew named the new molecule in honour of the part of the bird's anatomy that had provided the 'surprisingly abundant gift'.

Birdcage

This molecule is so called because it, um, resembles a birdcage, duh. Maybe it should have been used to capture the aberrant pigeon from cristane, above...

Apolloane and Rocketene

Apolloane was created at the same time as the Apollo 11 moon landings. When drawn as a flat diagram the structure bears a striking similarity to a rocket, with side fins and exhaust. And the OH is even located at carbon 11, to get apolloane-11-ol. Apparently, Neil Armstrong's personal memorabilia include a reprint of the chemistry publication which named it: [A. Nickon, et al., J. Am. Chem. Soc. 92 (1970) 1688.]
On a similar theme, Rocketene was also named for its structural resemblance to a rocket.

Thanks to Jarrod Ward for suggesting this molecule.

Manxane and Manxine

Manxane resembles the coat of arms of the Isle of Man (called a triskelion) which consists of 3 armoured legs in a circle. Bicyclo[3.3.3]undecane was named Manxane since it closely resembles this Manx emblem. Later on, a group of researchers at the University of Illinois created an analog of Maxane with a bridgehead nitrogen, and so called it Manxine. Professor Leonard, who created this molecule, thought Manxine sounded like a girl's name - so we now have the male (manxane) and female (manxine) versions of the molecule, with the difference being what is situated between their legs!

Cornerstone

Ok, this is a bit of a cheat, since its real name is b-corrnorsterone, but it's known as 'cornerstone' by all those that work with it. It got its name since it's a ketone with a norsteroid structure (hence 'norsterone') and the discoverer, Robert Woodward at Harvard, thought it might eventually be possible to transform it into a corrinoid.

Adamsite

This molecule was named after the renowned chemist Roger Adams of the University of Illinois. It's actually a chemical warfare agent, and is 'a damn sight' better at killing people than most other molecules...

BON-BONs

These ring structures are not what makes French sweets taste sweet. Heterocyclic dimers like the one shown in the picture (where you vary the R, R' and R" groups) are named from the fact that the ring atoms in sequence spell out BON-BON.

Performic Acid

An actor's favourite chemical? As you might expect from a per-acid, it's a very strong oxidising agent, and always puts on a great per-formance!

Thanks to Andy Dicks of the University of Toronto, for suggesting this molecule.

R-CMP

As anyone from Canada will know, RCMP are the initials for the Royal Canadian Mounted Police, but this molecule isn't their emblem. R-CMP is actually short for R-cytidine monophosphate, and is actually a component of RNA, the nucleic acid which transcribes the genetic information from the DNA so that it can be translated into protein.

Thanks to Amanda Musgrove from the University of Alberta, Canada (of course) for suggesting this molecule.

Sonic Hedgehog

Fruitfly genetics has a rich history of 'creative' nomenclature, often based on the appearance of flies that have the gene in a mutated form. One of these mutated genes made fruitfly embryos look like hedgehogs, since their spines grew all over their body rather than just in specific places - so it was name the 'hedgehog' gene. The vertebrate analogue was called 'Sonic' Hedgehog in order to distinguish it from its insect-forming version, and was given the abbreviation Shh. Geneticists studying other organisms are happy to elaborate on this when they can get away with it, and there are other variety of hedgehog genes called Indian hedgehog (Ihh), Desert hedgehog (Dhh), and even 'Tiggy-Winkle hedgehog' (TWhh)! There are also genes called Sleeping Beauty, Tubby, and most recently the puberty gene, "Harry Potter".
In early 2009, US scientists at discovered a potential inhibitor of the Hedgehog signalling pathway. One of the co-authors of the paper in Nature Chem. Biol., Lee Peng, of Harvard Medical School, said the team had a little fun with the naming rights to the new molecule. "As Sonic hedgehog was deliberately named after the Sega videogame character Sonic the hedgehog, we wished to adhere to the convention established by the original investigators in naming our inhibitor of Sonic hedgehog signalling," he said. "Dr Robotnik is Sonic's archenemy, so we decided that 'robotnikin' was an appropriate name for our compound." To me, robot-nikin' sounds like the occupation of a thief who steals androids.

Thanks to Greg Valure for suggesting this gene, and to Richard Williams from the Institute of Cancer Research and Geraldine VdA for providing some of the info about it, to David Bradley for the other gene names, and to Jan Linders for the robotnikin details. More fruitfly gene names and their stories can be obtained from http://www.flynome.com/, and thanks to Jeremy Bracegirdle for supplying this link.

Gibberelic Acid

Gibberelic acid isn't a psychotropic drug that makes you gibber insanely like a monkey...it's actually one of a number of gibberelins, which are plant hormones which control various aspects of plant growth.

Thanks to Mathias Disney for suggesting this molecule.

Darlingine

This molecule is lovingly extracted from the Brown Silky Oak tree, Darlingia darlingiana.. It hasn't been analyzed biologically yet, but may have activities similar to other tropane alkaloids, such as muscle contraction and stimulation...(But it only works if you treat it nicely...)

Thanks to Christopher Wells for info on this molecule.

Jesterone

This playful and mischievous molecule is found in a fungus, Pestalotiopsis jesteri, which lives inside yew trees.

Thanks to Christopher Wells for info on this molecule.

Trunkamide

Trunkamide has nothing to do with elephants, although its spacefill structure shown right looks a bit like an elephant. It was isolated from a sea squirt living in the Great Barrier Reef, and is reported to have anti-tumor properties.

Thanks to Christopher Wells for info on this molecule.

Diurea

As you might expect, this molecule and its derivatives are often used as a fertiliser, being splattered liberally around fields of crops. It's also known as biurea, but its proper chemical name is N,N'-dicarbamoylhydrazine. It's also sometimes used as flow improver in paints and greases. So next time you paint your house you can tell people you're covering it with diurea...

Thanks to Gene Morselander for info on this molecule.

Parisite

This mineral sounds like it grows on other minerals. It is found in Columbia, and it's named after J. J. Paris, who was a mine proprietor at Muzo, north of Bogota, Columbia. It is a member of the Bastnasite group of complex carbonate-fluoride minerals, and has the formula Ca(Nd,Ce,La)₂(CO₃)₃F₂.

Thanks to Tanuki the Raccoon-dog for info on this mineral.

Clintonite

This mineral sounds like it should be found in close proximity to 'internite' or 'lewinskyite'..., but it was actually named after American Statesman De Witt Clinton (1769-1828), not the notorious ex-President. Its formula is Ca(Mg,Al)₃(Al₃Si)O₁₀(OH)₂ (a calcium magnesium aluminosilicate hydroxide mineral), and it's related to margarite. It is found abundantly in the northern extent of New York.

Thanks to Friedrich.Menges and Steven A. Hardinger for info on this mineral, and to Hans Hillewaert for the link to the image.

Sodamide

This is the shorthand name given to the common chemical, sodium amide, NaNH₂. It sounds like it belongs in close proximity to other molecules in this list, such as arsole, anol, skatole, and maybe fruticolone...But I'm not letting it get anywhere near miazole!

Thanks to Germanicus Hansa-Wilkinson for suggesting this molecule.

dUMP

dUMP is the acronym for 2'-deoxyuridine-5'-monophosphate, and is an RNA transcription subunit - or a bit of the thing that makes proteins, and is one of the building blocks of DNA. dUMP is a deoxygenated form of RUMP, which is another of the bases found in RNA. If you want to have a 3D dump, click on the structure to the left.

Thanks to Christopher Putnam of the Ludwig Institute For Cancer Research, La Jolla, CA, and Peter Traill from the University of Dundee, and John Gosden for info on this molecule.

BARF

There are two molecules that are called by their shorthand name of BARF. The first, often written as BAr^F, is a halide abstracting reagent B[3,5-(CF₃)₂C₆H₃]₄^-, i.e. two CF₃ groups on each phenyl, and four of those phenyls on a boron. The second is written BARF, and is the shorthand for tripentafluorophenylborane (B-Ar-F), see structure on the right. It is mainly used as a strong Lewis acid to abstract a methyl group in the reaction to make a highly active ethylene polymerization catalyst. So you really can barf into a plastic bag...

Thanks to Ken Weakley for suggesting the second BARF, and to Thomas Vaid at Washington University for the first BAr^F.

Small-breasted-dog

Yes, it really is called that, but in Spanish! The molecule is actually named 'Perrottetin-a' which (almost) literally means "small-breasted-dog" (Perro=dog, tetita=small breast). The molecule gets its name from the liverwort plant from whence it is extracted, Hepatica Radula perrottetii, but I don't know why the plant is named after a small breasted dog?

Thanks to Enrique Pandolfi for providing the info on this molecule. See: Y. Asakawa, K. Takikawa, M. Toyota, T. Takemoto, Phytochem., 21, (1982) 2481.

Centaureidin

Centaurs are creatures which are half horse, half human. The molecule centaureidin got its name because it was extracted from a flower called Centaurea corcubionensis, which is related to the cornflower. It was discovered along with a molecule named centaurein, found in the same plant.

Thanks to Victoria Barclay from ACD in Toronto and to ShadowFox for providing the info on this molecule. Here is a scientific article about Centaureidin.

Sandwicensin

John Montagu, The Fourth Earl of Sandwich, was a notorious gambler who would often go from pub to pub in London on gambling marathons. To satisfy his hunger while continuing to gamble, he would order slices of meat between two pieces of bread. Thus, was the sandwich born. But how about "Sandwicensin"? As a newly identified cytotoxin, isolated from a soggy old sponge at that, we guess that it must be somewhat less than appetizing!

Thanks to Victoria Barclay from ACD in Toronto for providing the info on this molecule.

Magic Acid

'Magic Acid' is the name given to one of the strongest of the inorganic 'superacids'. It is made by mixing together antimony pentafluoride (SbF₅) and fluorosulphonic acid (HSO₃F), and it is so strong (pK_a = -20) that it is capable of protonating even saturated alkanes, like methane, to produce carbonium ions. On a similar name theme, Magic Factor-1 (derived from the acronym for Met-Activating Genetically Improved Chimeric Factor-1) is an engineered protein that helps keep certain cells alive and which may be used to treat muscular dystrophy. It's been shown to improve the running speed of mice which have previously had wasted leg muscles...magic indeed!

Thanks to Indranil Sen from the Utah State University for suggesting magic acid, and to Rob Towart for Magic F-1 (See: M. Cassano, et al, PLoS ONE 3, (2008) e3223).

Profilactin

Actin is an intracellular fiber protein (best known in muscle contraction), and profilin is a protein that interacts with actin to "promote filament" formation. When profilin and actin are bound together, the complex was originally labelled: "Profilactin", which is most appropriate since it was first isolated in sea urchin sperm. However, I'm told this name was not officially recognised. Also, the first submission of a name for this protein was "screw-in"...because when the filament is ejected from the tip of the sperm, the globular actin shoots outward in a screwlike motion. Although this, too, was a clever name given the protein's location...it was turned down as well. Its official name is now 'the profilin-actin complex'.

Thanks to Blair Boehmer from Duke University, Shefa Gordon at Berkeley and to Leigh Arino de la Rubia for info on this molecule.

Profilin bound to an actin monomer. The profilin protein molecule is shown in blue and the actin in red. ATP is shown in green. [Modified from the original image in 'Molecular Biology of the Cell' by Alberts, et al.]

Crocidolite

This has nothing to do with crocodiles, but is actually the name of the mineral form of blue asbestos, with formula Na₂Fe₅Si₈O₂₂(OH)₂. It either got its name from the Greek word for 'woolly', or it was named from the geographic location of where it was first discovered. viz. the Crocodile River Valley in South Africa. This is just outside Nelspruit in Mpumalanga South Africa (look on the Eastern part of a SA map - next to the Kruger National Game Park).

Thanks to Indranil Sen for suggesting this molecule and to Stuart Kidd and Grant Little for providing some of the information about it.

Bellendine

For non-English readers, I won't tell you what 'bell-end' is slang for, but a clue might be that the molecule is extracted from the flower Bellenda Montana, which should have a purple head...

Piano Stool

These are a group of molecules made from a transition metal bonded to a cyclopentadienyl ligand, so that the resemble a 3-legged piano stool. I don't know if molecules have been made with other numbers of 'legs', such as milking stools, etc.

Thanks to Sean Pearce for suggesting this molecule.

Megatomic Acid

This molecule has nothing to do with nuclear explosions, and neither is it the magic formula that creates a superhero. But it is in fact named after the black carpet beetle Attagenus megatoma (Fabricius), in which it is the principle component of the beetle's sex attractant. Its proper name is (3E,5Z)-3,5-tetradecadienoic acid.

Thanks to Simon Cotton for suggesting this molecule, and for more info see: New J.Chem. 25 (2001) 223.

Grass-Hopper Ketone

I'm guessing that this molecule gets its name as a result of laziness. It's extracted from the defensive secretions of the flightless grasshopper Romalea microptera, and I assume that after spending hours in the field, annoying the grasshoppers, and then catching them and 'milking them', the scientists involved were too tired to think of a proper IUPAC name, so they came up with the inspired name, grasshopper ketone.

Thanks to Polyploid2 for suggesting this molecule, and for more info see: J. Meinwald and L. Hendry, Tetrahedron Lett., 1657 (1969)

Shattuckite

This mineral sounds painful, but is actually just named after the locality in which it is found, the Shattuck mine in Arizona. Its actual formula is Cu₅Si₄O₁₂(OH)₂.

Thanks to Martin Harris for suggesting this mineral.

G(olf) proteins

These are a class of proteins called G-type proteins, some of which are linked to the olfactory system - hence the name G(olf) proteins. They help trigger the biochemical synthesis of neurotransmitters, which eventually leads to signalling, and gives us a sense of smell.

Thanks to Boaz Laadan for suggesting this mineral. More info at: http://www.leffingwell.com/olfact3.htm

Germylene

The GeH₂ radical is called germylene, which is similar to an antiseptic ointment found in the UK called Germolene. I doubt that germolene contains germylene, though, as GeH₂ is very toxic...

Thanks to Victor Sussman for suggesting this molecule.

Khanneshite

It's amazing how this name got past the International Mineralogical Association when they approved the new mineral name. It was named after the discovery locality at Khanneshin, Afghanistan. All minerals have the suffix '-ite'. and so the name they gave to this mineral is - Khanneshite. I can only presume that there were no Scots on the committee that approved the name... I can't find any photos or structural images of khanneshite, so the image on the right is actually of the burbankite structure which, according to the literature is identical to that of khanneshite.

Thanks to Brian Jackson from the National Museums of Scotland for suggesting this mineral.

BCNU

Bis(Chloroethyl) NitrosoUrea has got quite an appropriate acronym, BCNU (be seein' you...), since in early medical studies it was found to be so toxic, it killed the patient! It is actually highly carcinogenic, causing tumors in rats, mice, rabbits, and probably humans as well. Ironically, it is actually used as a treatment for brain cancer and other diseases such as Hodgkin's lymphoma.

Thanks to Terence Bartlett for suggesting this molecule.

SEX

SEX is the official abbreviation of sodium ethyl xanthate, which is a flotation agent used in the mining industry. Apparently you can get SEX in both solid and liquid forms (should that be hard and wet SEX?), and according to Australia's National Industrial Chemicals Notification and Assessment Scheme signs of high exposure to SEX include 'dizziness, tremors, difficulty breathing, blurred vision, headaches, vomiting and death'. Sound familiar...?
On a related note, there's another flotation reagent, KAX, potassium amyl xanthate, which has the same function, and the same smell!

Thanks to Joseph Wiman and for suggesting this molecule and Nicholas J. Welham for some of the info about KAX.

Austin

Austin has nothing to do with Austin cars, Austin Texas, or even Austin Powers...it's actually a mycotoxin, which comes from the fungus Aspergillus ustus, which might have given it it's name but I'm not sure.

Thanks to Chris Fellows for suggesting this molecule and to Mark Johnston for suggesting how it got its name.

Pantolactone

This molecule sounds like it belongs in underwear, or on stage in a pantomime. As you might expect, it is used as a reagent in the synthesis of CAMP ligands (cis-2-(aminomethyl)-1-carboxycyclopropane)...

Thanks to Gary Randall for suggesting this molecule.

Technetium Cow

'Cow' terminology comes from the nuclear industry, and it has nothing to do with the unfortunate cattle that live near nuclear power plants. A radionuclide, such as ⁹⁹Mo (as its ammonium salt), is stored in a column, called a 'cow'. Its decay product, technetium-99m, is continually produced, and it can be flushed out of the "cow column" in a process called 'milking the cow'. The 'technetium cow' isotope is then used in bone scans, and has a 6 hour half-life. And I'm told that there used to be an 'Americium Cow' in Harwell in the 1950s. On a related theme, molybdic acid anhydride (MoO₃) is often referred to as 'Moo'.

Thanks to 'Plutonium' Page Sebring for providing the info about this element, Ian Ferguson for the Am Cow info, and to Jonathan Montgomery for info on Moo.

Erectone

No, this isn't one of the ingredients in Viagra...but is actually one of a group of compounds extracted from the Japanese/Chinese herb Hypericum erectum, which is often used in traditional Chinese medicine to treat arthritis, rheumatism, and as an astringent.

Thanks to Christopher C. Wells for providing the info about this molecule.

Abiguene

Ambiguenes are cytotoxic and fungicidal indole alkaloids that are extracted from blue-green algae. As many as 7 are known. Although it could just be 5. Or 10. Or maybe they are a different type of molecule altogether...? It is very appropriate that in 1980 Pelletier et al. had to revise the original structure, since it was wrong the first time around.

Thanks to Christopher C. Wells for providing the info about this molecule. See: S.W. Pelletier et al, J. Am. Chem. Soc. 103 (1981) 6536.

Lovenone

This is a cytotoxic agent isolated from the skin of a nudibranch (of course) Adalaria loveni which lives in the North Sea.

Thanks to Christopher C. Wells for providing the info about this molecule.

Boldine

This is an aporphine alkaloid extracted from the plant Peumus boldus. It is a good antioxidant and can protect the liver, although there are rumours it makes your hair fall out...

Thanks to Christopher C. Wells for providing the info about this molecule.

Inflatene

This is a hydrocarbon compound that is isolated from soft coral (Clavularia inflata) and is apparently toxic to fish - maybe it makes them all look like puffer fish ;-).

Thanks to Christopher C. Wells for providing the info about this molecule.

Bowtiediene

This is another molecule named after its shape - although the preferred name is spiropentadiene.

Thanks to Isaiah Shavitt for providing the info about this molecule.

Prodigiozan

This molecule has a name that sounds like the Biblical 'prodigal son', who finally returned home. The structure shown is actually the related molecule, prodigiosin, since I can't find the structure of Prodigozan...well, not until it finally comes back here. :-) Both molecules are antibiotic pigments produced by Chromobacterium prodigiosum, with antimicrobial and cytotoxic properties.

Thanks to Susanne Wikman from Vaxjo University, Sweden, for providing the info about this molecule.

Arachidonic Acid

This molecule sounds like it has something to do with spiders, but it's actually made in the human body. It is synthesised from linoleic acid and plays an important stage in the inflammatory process of the human body - some Non-Steroidal Anti-Inflammatory Drugs (NSAID's) are believed to work by inhibiting this stage. But nobody has managed yet to artificially produce medical grade arachadonic acid (it's mainly used in infants) so the only source is rats urine - it needs a day's worth of urine from 10,000 rats to produce a single dose! Now, that really is taking the p***!

Thanks to Mark Croker for providing the info about this molecule.

Warfarin

This molecule sounds like it could be a warfare agent, and it is...if you're a rat. It's a rat poison which stops the blood clotting, so the rats bleed to death. It also has medical uses in blood thinning and clot prevention. Apparently it gets its name since WARFarin was the first patentable product of the Wisconsin Alumni Research Foundation (WARF). An interesting story about warfarin is that it may have been used to kill Stalin.

Thanks to Charles Turner and Michael Bailey and Larry Baum for providing the info about this molecule.

(R)-DICHED

This is the abbreviation for (R,R)-1,2-dicyclohexyl-1,2-ethanediol. The authors of the paper which describes it (Organometallics, 2001, 20, 2920) state "a number of DICHED boronic esters were screened by NMR...". I wonder who the real DIC-HED is?

Thanks to Alex Yuen of the University of Sydney for providing the info about this molecule.

Lunatoic Acid

Lunatoic acid is an azaphilone isolated from Cochliobolus lunatus. It is a good antibiotic and also causes sporation in fungi. Perhaps it kills bacteria by causing them to die by insanity, in the same way canine distemper kills animals.

Thanks to Christopher Wells of the University of Sydney for providing the info about this molecule.

Microlite

Microlite is not one of the components of a small airplane, but is a tantalum/niobium oxide mineral that can be slightly radioactive. Its correct formula is: (Ca, Na)₂Ta₂O₆(O, OH, F).

Thanks to Neil Brew for suggesting this mineral. More info can be found here.

beta-BuTX

This molecule sounds like the sales pitch for an exercise regime (get better buttocks using this!), but it's actually a snake venom with full name beta-Bungarotoxin). maybe the venom is more potent if the snake bites you on the Butx. :-)

Thanks to Satan's Little Helper and Joerg Fruechtel for info on this molecule.

DAMN

DAMN is the acronym for diaminomaleonitrile, which is a particularly nasty molecule containing lots of cyanide groups.

Thanks to Michael Stewart for suggesting this molecule.

"Frankly my dear, I couldn't give a Diaminomaleonitrile..."

Allene

Allene is quite a sad molecule in Holland, since in Dutch it is called 'alleen', which simply means 'alone'. And if you add a benzene-ring you'll get Benzo-allene which means "I'm so lonely" in Dutch. Ahhhh....

Thanks to Karel Vervaeke and Harmen Lelivelt for info on this molecule.

Proton Sponge

This molecule is 1,8-bis(dimethylamino)naphtalene, and according to the Aldrich Chemical Catalog, it is a very strong base with weak nucleophilic character due to steric effects. Therefore it goes by the nickname 'proton sponge', since it mops up all available protons.

Thanks to Fernando Perna for info on this molecule.

Mirasorvone

This molecule is part of the defensive chemistry of Thermonectus marmoratus, a beetle recently named the "sunburst diving beetle". The discoverers' at Cornell University named it in honour of the actress Mira Sorvino (right), who, as Dr Susan Tyler in the motion picture Mimic, successfully confronted the ultimate insect challenge.

Thanks to Andy Cal for info on this molecule, and more info is available at: http://www.pnas.org/cgi/content/full/95/6/2733.

Stichtite

Stichtite is a lilac coloured mineral which is a hydrated magnesium chromium carbonate hydroxide. This is fairly common as streaks and small lenses in the green Serpentine in the metamorphic rocks of Western Tasmania, but is very rare elsewhere. It was named after Robert Sticht, a director of a mining company.

Thanks to Martin Harris for info on this mineral.

Cumene

Luckily, this molecule is actually pronounde 'coo-mene', so as to avoid sticky problems when ordering it. It's a fairly standard organic solvent, with a distinctive odour, that is used to make resins, polycarbonate, synthetic fibers such as nylon, and other plastics. Although pronounced the same, it has nothing to do with the Indian curry spice, cumin.

Thanks to J.J. Keating for info on this molecule.

Flea

This is the commonly used name for the amphetamine, N-hydroxy-N-methyl-3,4-methylenedioxymethamphetamine (the N-hydroxylated version of MDMA, Ecstasy). The origin of its name is a bit strange, and is related to the fact that a commonly used code name for the parent compound, MDMA was ADAM. The 6-Methyl homologue was then called MADAM, and, following this pattern, the 6-Fluoroanalogue was to be FLADAM. So, with the N-Hydroxy analogue, the obvious choice was HADAM. But this brought to mind the classic description of Adam's earliest complaint, an infestation of fleas. The poem was short and direct: "Adam had 'em." So, in place of HAD 'EM, the term FLEA jumped into being.

See: http://www.erowid.org/library/books_online/pihkal/pihkal081.shtml for a full description of this naming process. Thanks to J.J. Keating for info on this molecule.

Wheelbarrow Molecule

Here's a molecule that has been designed to look like a wheelbarrow. It doesn't seem to have a full name yet, so it's just called Wheelbarrow Molecule. What's next, a molecular lawn mower? Pruning shears?

Thanks to Plutonium Page for info on this molecule, and the full paper can be seen at: Tet. Lett. 44 (2003) 6261.

Syringic Acid

This molecule is named after the lilac plant, since the Latin name of lilac genus is Syringa. Lilac bushes possess hollow sticks which were used in ancient times to make flutes. In fact, there is a kind of flute that is called "siringa" in Spanish. In Latin the meaning of the word siringa was extended to include hollow tubes made of any material, including metal. Later, when hollow needles began to be used to inject liquids in the body, quite naturally they were called syringes. Funnily enough, syringic acid can be found in blueberry plants, which, in Latin, are called Vaccinium. Quite a coincidence! On a related theme, there is also a Vaccenic acid (Z-11-octadecenoic acid, also known as asclepic acid) although its structure is not related to that of Syringic Acid.

Thanks to Andrei V. Rogoza, Kastytis Beitas, Gabriel Tojo and to ShadowFox for info on this molecule, and to Tue Bruun Petersen for the info about vaccenic acid./p>

Tortuosine

This molecule is an alkaloid extracted from the plant Amaryllidaceae, but I bet it was extracted very sloooowwwllly. In fact, this naturally occurring organic compound and the following one (assoanine) had plant-derived names that were so compelling that Lee Flippin designed and executed total syntheses of them just for the fun of it.

Thanks to Lee Flippin for info on this molecule. More details: J. Org. Chem., 65 (2000) 3227.

Assoanine

This molecule gets its superb asinine name from the plant from which it is extracted, the gloriously named Narcissus assoanus!

Thanks to Lee Flippin for info on this molecule. More details: J. Org. Chem., 59 (1994) 3497.

Bicyclohexyl

This molecule not only has a name that sounds like a bicycle, ironically it even looks like one too. In fact, the bicyclohexyl compound with isopropyl and methyl sidechains (2-isopropyl-3'-methylbicyclohexyl, shown in the diagram) looks even more like a bicycle. There is also tricyclene, but unfortunately its structure looks nothing like a tricycle.

Thanks to Joris van den Heuvel for suggesting this molecule and to Geoff Hallas for correcting the structure.

NanoPutian Molecules

And today's award for the 'How did they possibly get a grant to do that?' paper, goes to the J. Org. Chem. article by Chanteau and Tour from Rice University in Texas. It concerns making anthropomorphic molecules - i.e. molecules that look like humans...but why anyone would want to do this I don't know... They have been named NanoPutians, after the little men from Lilliput in the book 'Gulliver's Travels'. They come in many forms - the basic building block is the NanoKid (shown right), and from this other variants can be made, such as NanoAthlete and NanoBaker.

Thanks to Neil Edwards for suggesting these molecules.

Nanocars and Nanotrikes

These are the perfect vehicles for driving Nanoputians around their nanoworld. They are made from a rigid framework of benzenes and acetylene groups, with either three or four C₆₀ molecules attached at the ends as 'wheels'. I always wanted a compact...

Thanks to Andrew Byro for suggesting these molecules.
See: Y. Shirai et al, Nano Letts. 5(11), (2005) 2330.

Anisole

Anisole sounds like a molecule the devil would be very interested in collecting, or maybe it's James Brown's ('The Godfather of Soul') favourite molecule? Anisole is aromatic in both the chemical and olfactory sense, and is used in perfumery. It is also an insect pheromone. If you have a lisp, please don't confuse anisole with anethole, which is a structurally related natural product which, incidentally, has the flavour of aniseed.

Thanks to Eric van der Horst for suggesting this molecule and to Matthew Piggott for providing more info about it.

Dopamine

Dopamine (pronounced DOPE-a-mean) is a neurotransmitter in the brain. It is connected to pleasurable sensations (feeling doped) and has been shown to be connected to drug abuse and addiction. Maybe that's why Dopey always had that silly grin on his face...

Thanks to Andrew Byro for suggesting this molecule.

BIG CHAP

This wonderfully named molecule has nothing to do with reproductive hormones, but is actually a detergent with proper name N,N-bis(3-D-gluconamidopropyl)cholamide. Apparently the molecule has reduced electrostatic interactions that prevent your BIG CHAP getting stuck in a chromatography column...

Thanks to Stephen FTM Thompson for suggesting this molecule.

ASS

This is the commonly used acronym for argininosuccinate synthetase, which is a chemical found in the brain. So it seems some people really do think with their ASSes...

Thanks to Allart Kok for suggesting this molecule.

Horseradish Peroxidase

This is the version of the peroxidase enzyme that is isolated from the horseradish plant. Like all peroxidases, it converts harmful peroxide molecules (H₂O₂) into water molecules (H₂O). It is also used to label proteins and nucleic acids as an alternative to radio labelling. The molecule to be labelled is attached to the horseradish peroxidase molecule, and the mixture is then exposed to a substrate that changes from clear to coloured when it is oxidized by HRP. When some of the variations of this enzyme are used as a labels for antibodies, they go by names such as anti-mouse, anti-rabbit, and worryingly...anti-human.

Thanks to Andrew Patterson for suggesting this molecule.

Kojik Acid

This sounds like Telly Savalas' favourite molecule. He was the star of the US TV cop show from the 1970s called 'Kojak'. Kojic acid is used as a skin whitener...but does it work especially well on bald heads?

Thanks to Jerry Van Cleeff for suggesting this molecule.

Porkane

I'm pretty certain this is a spoof molecule, since one of the carbons has 5 bonds. These pig-shaped molecules, where the 'tail' can point up or down, are apparently isolated from porcine lard (pig fat). There are various derivatives of this, including norporkanone, epiporkanone and neoporkanone. For more info on the porkanes, see here.

Thanks to Victor Nikolaev for suggesting this molecule.

Spiroagnosterol (Vice Presidential Steroid)

Years ago this molecule was called the "Vice Presidential Steroid" because of the similarity in name to Spiro Agnew. Mr Agnew was, of course, the Vice President of the U.S. from January 1969 until October 1973, when he resigned. (I've never found a proper reference to this molecule in the literature - does anyone have it?)

Thanks to John L. Meisenheimer, Sr for suggesting this molecule.

Nagarse

Nagarse is a broad-specificity protease, also known as Bacillus amyloliquefaciens subtilisin. It seems to be used to break apart proteins and DNA strands for analysis purposes. Its source is a bacterium and a leech (hirudo medicinalis).

Thanks to Richard Cammack for suggesting this molecule.

Hardwickiic acid

This is a diterpene which got its name since it was first isolated from the Indian tree Hardwickia pinnata. I assume the tree was named after someone called Hardwick. Anyone know?

Thanks to J.J. Keating from University College Cork for suggesting this molecule and to ShadowFox for more info about it. Ref: R. Misra, R.C. Pandey, S. Dev, Tetrahedron 35 (1979) 2301.

Aristolochic acid A

This aristocratic sounding molecule is derived from species of the birthwort plant (aristolochia). Plants containing the compound were used in herbal medicine as anti-inflammatory agents, but they are now banned in the US and Europe as the compound is nephrotoxic (toxic to the kidney).

Thanks to J.J. Keating from University College Cork for suggesting this molecule. Ref: Fundamentals of Pharmacognosy and Phytotherapy by M. Heinrich, J. Barnes, S. Gibbons and E. Williamson (Churchill Livingstone, 2004., pg 165)

CAMP

This is actually short for cyclic adenosine monophosphate (cAMP) and is a signalling molecule which can be found in almost all eukaryotic organisms. For example, it is used as a nutrient sensor in yeast, and is one of the building blocks of DNA. I wonder if it's responsible for the so-called 'gay gene'...

Thanks to Han Lim for suggesting this molecule and to Tom for info about it.

Cucurbituril

This molecule, which is shaped like a Halloween Jack'o'Lantern, is named after the Latin word for pumpkin (Curcubita pepo). It is now finding lots of use in medical drugs or in potential molecular electronic devices due to the fact that other long thin molecules can be threaded through the hole in the centre to make so-called 'rotaxanes'.

Hipposudoric Acid

This is a malodorous blood-red pigment found in hippo sweat. It absorbs ultraviolet light, thus blocking out the sun's rays like a sunscreen. It is also a natural antiseptic. Its red colour is responsible for the myth that hippos sweat blood.
And still on the hippo theme, there's a molecule called Hipposulphate A, which is a poisonous sulfated sesterterpenoid that's found in a sponge, Hippospongia metachromans, living near Okinawa.

Thanks to Charles Turner for suggesting Hipposudoric Acid, and to Christopher Wells for Hipposulphate A.

Old Yellow Enzyme

This is a flavoprotein that reversibly oxidises NADPH to NADP and a reduced acceptor. In fact, yellow enzymes are any of a number of enzymes having a flavin as a prosthetic group. Historically, NADPH dehydrogenase (occurring in plants and yeast) was called the Old Yellow Enzyme to distinguish it from D-amino acid oxidase, known as, of course, the New Yellow Enzyme.

Thanks to John Moody for suggesting this enzyme.

Ladderane

Ladderane is a chain of fused cyclobutane rings that make up the bulk of dense membranes in certain unusual bacteria. They were discovered in anammox bacteria, which anaerobically oxidize ammonia to dinitrogen. The staircaselike structure of cis-fused cyclobutanes has never before been seen in nature. The most abundant lipid in the bacteria is the methyl ester of a C₂₀ fatty acid with five fused rings. Other ladderane lipids contain three fused cyclobutane rings attached to a cyclohexane.

Thanks to Erik Holtzapple for suggesting this molecule.

Snottites

These are gelatinous, dripping microbial draperies ("mucus stalactites") composed of elemental sulphur, iron oxide crusts, gypsum, and densely packed bacteria, and are found in caves. They are formally known as biovermiculations, although snottite is more descriptive. Snottites are produced by sulfurphilic micro-organisms and drip sulfuric acid with a pH of 0.3 to 0.7. Other microbial structures include "blue goo," which are lavender structures attached to the walls of the cave, and "red goo," a complex clay breakdown product containing clusters of bacterial cells and having a pH ranging from 3.9 to 2.5. Other microbial stalactites go by the fancifully names of "phlegm balls," "green slime," "punk rocks," "hairy sausages," "slime balls," and "beads on a string."
On a similar theme we also have: Coprolites, which are fossil feces, Regurgitalites, which are fossil vomit or pellets, and Cololites, fossilised stomach, gut, or colon contents.

Thanks to Charles Turner for suggesting these.

Coalingite

This superbly named mineral takes some licking... It is actually an interstratified hydroxyl carbonate, but whenever anyone says its name, they normally lower their voices for the rest of the discussion, probably because it sounds like a contraction of coitus and lingus. But it was fact a mineral named after being found in the vicinity of the town of Coalinga, California, which was itself named after 'Coaling Station A'.

Thanks to Phillip W Barak of the Virtual Museum of Minerals and Molecules for suggesting this mineral.

Nootkatone

This molecule with a very silly name is used as a food additive to give grapefruit flavours, as well as in the perfume industry to give odours of citrus fruits and orange peel. It got its name from the yellow cedar, or Camaecyparis nootkatensis, which was itlself named after the native North American called the Nootka.

Thanks to Jim Gobert for suggesting nootkatone and to ShadowFox for some info about its name. Click here for more info on the structure of nootkatin.

Bullvalene

This is a very unusual molecule, in that it is fluxional...all the carbons are equivalent due to the rapid movement of the double bonds around the structure. It was first predicted to be like this over 20 years ago by Professor 'Bull' Doering, and was only synthesised in the lab many years later, whereupon his controversial predictions about the structure were verified. The origin of the name is unclear. It is thought to be derived either from his nickname, 'Bull', or from his seminars were affectionately(?) known as Doering's 'bull sessions', since it was at one of these that the structure was first written on the board. Other reports, however, suggest that it was given its name by an irreverent and skeptical graduate student that thought such a structure couldn't exist, and so called it 'Bull-valene'.

Thanks to Marc Kaminski of the University of Freiburg for suggesting this molecule, and to John Perkins for info about the name origin. See: J. Chem. Edu. 78 (2001) 924, for more info.

Barrelene

This molecule is closely related to bullvalene, and got its name from its similarity to the shape and structure of a barrel. Peter Lykos emailed me to say how it happened: "When Howie Zimmerman was getting started at Northwestern University I heard he had synthesized a molecule that in effect was three ethylene molecules condensed about two methyl axes. I could not give it the correct organic chemist's systematic name (I am a quantum chemist) but was fascinated by the notion that there might be a delocalization of six π-electrons around the molecule. So when I called him about its spectroscopic properties I referred to it as 'barrelene' following the idea that the lateral delocalization mught be like the staves of a barrel. He apparently liked that name so that became its trivial standard name".

Thanks to Peter Lykos for suggesting this molecule.

SnOT

Tritiated tin hydroxide goes by the wonderful chemical formula of SnOT. David Ball, a chemist in Cleveland Ohio, was working on isotopomers of SnOH, and after tritiating it found he got SnOT. His paper concludes with the wonderful phrase "Since Wang et al did not use tritium substitution, we can state with certainty that there was no SnOT in their samples".

Thanks to David Ball for studying SnOT and suggesting it for this page. See: D.W. Ball, J. Mol. Struc. (Theochem) 626 (2003) 217, for more info. Thanks also to Sky for the use of the photo of him playing a beggar in a re-enactment of the English Civil War for the Sealed Knot Society.

DOPE

Apparently, DOPE is commonly used by membrane chemists and biochemists - which is something I've always suspected... It's actually short for 1,2-Dioleoyl-sn-Glycero-3-Phosphoethanolamine, and it's a phospholipid used for research into membrane structures. A variant on this is called DOGS, so if you take DOPE, you may go to the DOGS...

Thanks to Sophie Weiss of Leeds University for suggesting this molecule. More info from http://www.avantilipids.com/

Flufenamic Acid

This molecule with a very fluffy name has anti-inflammatory and antipyretic properties, and is used to treat inflammatory rheumatoid diseases and relieve acute pain. Its chemical name is N-(3-trifluoromethylphenyl)anthranilic acid, which doesn't sound quite as friendly and fluffy as its common name. In other languages it is called Flufenaminsäure (German), flufenaminezuur (Dutch), ácido flufenamico! (Spanish), and acide flufenamique (French).

SNOG

SNOG is a utility carrier of nitric oxide which breaks down to produce nitric oxide and a glutathione radical at pH 7.4. Its proper chemical name is S–Nitrosoglutathione. Unsurprisingly, one effect of SNOG is that it apparently causes smooth muscle relaxation... For those of you unfamiliar with UK slang, a 'snog' is a deep passionate kiss, similar to the one Britney is giving Madonna in the photo on the right...

Thanks to Mackay Steffensen from Oxford University for suggesting this molecule.

Hirsutene

This is an important biological molecule, although what its function is, I'm not sure. Perhaps it makes things hairy...?

Forskolin

Despite the odd name, forskolin is not what they remove from the baby during ritual circumcision. In India, practitioners of traditional Ayurvedic medicine have long used the herb Coleus forskohlii to treat asthma, heart disease, and a range of other ailments. In the 1970s, researchers isolated a chemically active ingredient in the herb and called it forskolin. Now available in supplement form, this extract is commonly recommended for treating hypothyroidism, a condition in which the thyroid gland produces too little thyroid hormone. Forskolin is believed to stimulate the release of thyroid hormone, thus relieving symptoms as fatigue, depression, weight gain, and... dry skin.

Thanks to Kyle Daly for suggesting this molecule.

Wrenchnolol

This is a molecule that looks like a wrench, and is an anti-cancer drug. The "jaw" part of the compound mimics the helical interface of the activation domain of a transcription factor molecule, and the "handle" region accepts chemical modifications for a range of analysis.

Thanks to Mackay Steffensen for suggesting this molecule. More details: J. Am. Chem. Soc. 126 (2004) 3461.

Sex Muscle Abnormal Protein 5

The European Bioinformatics Institute houses the Macromolecular Structural Database, and for quite a few years the most downloaded structure from that site was PDB code 2SEM: it contained a protein called "Sex muscle abnormal protein 5". Obviously, search engines had indexed all the PDB files, and you can guess what kind of searches had returned this structure! The protein comes from Caenorhabditis Elegans, which is a tiny worm (about 1 mm long) and was the first true animal to have its genome completely sequenced. The people who reported this protein were investigating its crucial role in the development of the worm's vulva (Clark et al, Nature, 1992 Mar 26, 356(6367):285-6). As the amount of dubious material available on the internet has grown, interest in this protein from persons 'outside the scientific community' has declined. On a similar theme, there's another molecule called SexA I, which is a restriction enzyme from Streptomyces exfoliatus that cleaves the DNA sequence A/CCWGGT.

Thanks to Peter Keller of the Macromolecular Structural Database, European Bioinformatics Institute, and Lily Zhou from the University of Michigan, for suggesting these molecules and telling me their details.

Sillimanite

This mineral wasn't named after the clumsy fool that tripped over it, but was named in honour of the American mineralogist Benjamin Silliman (1779-1864), who was a chemistry professor at Yale. It is a form of aluminium silicate, with no real value, except in Idaho, where the Clearwater River Valley has sillimanite cobbles that are carved into figurines and sold as souvenirs of Idaho.

Thanks to Hope Nesmith for suggesting this mineral.

Indenyl

This sounds like it could be a pollutant found in some Egyptian rivers (i.e. in de Nile...), but it's actually a fusion of a cyclopentadienyl ring with a benzene ring, and is often used as a ligand for metallocene synthesis.

Thanks to Kenneth Koon for suggesting this radical.

Thebacon

This molecule certainly brings home the-bacon. It has a similar structure to diamorphine (heroin) but has only one acetyl group instead of two, and the other group is replaced with a CH₃O- group. Apparently, thebacon hydrochloride is a centrally acting cough suppressant sometimes used to treat coughs. This molecule isn't to be confused with BaCoN (barium cobalt nitride), which is a black crystalline solid with a layered structure (strips of BaCoN?)

Thanks to Matt Wright from University Hospital Birmingham NHS Foundation Trust and Aston University, and Bastiaan Vos for suggesting these molecules. More info in BaCoN from: A. Tennstedt and R. Kniep, Z. anorg. allg. Chem. 620 (1994) 1781.

Cryogenine

Cryogenine A (also known as Vertine) is the active constituent of Sinicuichi plant. It apparently can give audio hallucinations, but I don't know why it is called cryogenine...maybe because after you stop using it you go through very, very cold turkey? In fact there are two totally unrelated, and different molecules called cryogenine. The other one, Cryogenine B, is usually called phenylsemicarbazide, and has been found to be carcinogenic in mice.

Thanks to Michael F Aldersley from Rensselaer Polytechnic Institute, Troy, NY, for suggesting this molecule, and to Fox for info on Cryogenine B.

Lagerine and Bebeerine

I wonder if lagerine is sold by the pint? It actually has nothing to do with beer, it gets its name from being a constituent of the crape myrtle (Lagerstroemia indica L.) plant. Bebeerine too, has nothing to do with beer. It's an alkaloid molecule derived from the Caribbean bebeeru tree, and helps to protect it from beetles.

Thanks to Michael F Aldersley from Rensselaer Polytechnic Institute, Troy, NY, for suggesting this molecule. Ref: E. Spath, F. Kuffner, Ber. Deutch Chem. Gess. 67 (1934) 55.

Jawsamycin, Histrionicotoxin and Yessotoxin

These three molecules are all highly toxic, and are normally isolated from biological sources. Jawsamycin was discovered in 1989 by Fujisawa, a Japanese pharaceutical company, it has only recently been synthesised. The metabalite is composed of a chain of five carbon triangles (cyclopropyls), giving it its name because of the resemblance to shark's teeth. The compound, however, has 10 chiral centres, points about which mirror images of the molecule can form for a total of 1024 possible isomers, only one of which is jawsamycin.
Histrionicotoxin is a poison found on the skin of a certain tree frog in South America (Dendrobates histrionicus), and is used by the native indians on their blow-pipe darts.
Yessotoxin was first isolated from the digestive organs from scallops (Patinopecten yessoensis) in Japan and is believed to be produced by microalgae.

Thanks to James Waterman from Nottingham University for suggesting these molecules.

Sarcosine

This is one for all our French readers... Nicolas Sarkozy (right) is currently the President of France, and, as such, it's appropriate that he has a molecule with a similar name. Sarcosine is a sweetish crystalline amino acid found in muscles and other tissues, and is also called N-methylglycine.
Another molecule which sounds odd in French (but not in English) is pyralene, which has been used in the past as an insulating oil in electric transformers. In French it is pronounced "pire haleine", which means "worst breath". This is ironic, since use of pyralene was abandoned after transformer fires were giving off toxic fumes.

Thanks to Thomas Jeanmaire for suggesting sarcosine, and Marc Schaefer for pyralene.

Enflurane

Yet another one for the French speakers... Enflure in French means a twit, a clot, or a jerk, or can also mean a swelling or inflamation. Enflurane is an outdated halogenated ether that was commonly used for inhalation anesthesia during the 1970's and 1980's. A curious (but apparently true) story about enflurane relates to its pre-human work. Enflurane and Isoflurane are isomers, and they were being investigated for their safety and efficacy as anaesthetics. Isoflurane is by far the better of the two, but was initially held back from clinical use because test experiments showed it gave cancer to rats. It turns out that the rats that were given enflurane were given different food to the ones using isofluran, and those exposed to isoflurane were being fed pellets which had become contaminated with a known carcinogen. By the time the toxicity experiments were repeated (and isoflurane found to be innocent in this regard), the poor relation, enflurane (which had passed all the previous tests with flying colours), had already been on the market for a few years. Had the contamination not occurred, it is doubtful that enflurane would ever have made it on to the market at all. Enflurane was never popular, and its manufacture has ceased because the makers could not sell enough of it to make its production economical. Isoflurane, meanwhile, led the way as the mainstay of inhalational anaesthesia in the Western world for several decades.

Thanks to Thomas Jeanmaire for suggesting this molecule, and to Ken Ruiz for the isoflurane story.

Shikimic Acid

Here's one for our German-speaking readers. Shikimic sounds very like the German word 'Schickimicki', which means a (snobbish) member of the in-crowd, a trend-setter, or a 'designer-label-wearing' sort of person, for example, Posh and Becks in the picture, left. Shikimic acid was first isolated from the Japanese flower shikimi, hence its name. It's used as a starting molecule in the synthesis of the anti-flu drug Tamiflu.

Thanks to Kutti for suggesting this molecule.

Mandelic Acid

Mandelic acid is not named after Nelson Mandela, the world famous South African polician and winner of the 1993 Nobel Peace Prize, although his youthful appearance might be due to it....as mandelic acid is often used in skin creams to smooth away wrinkles. It's also used as an antiseptic ingredient particularly against urinary tract infections. An interesting related anecdote is that a chemist called Leon Mandel from Emory University in the US, gave a talk at Princeton in the mid-60s on the total synthesis of leontine, an alkaloid. He said his final step was to be the reaction of leontine with mandelic acid (yielding, of course, leon(tine) mandel(ate)).

Thanks to Antony Bigot for suggesting this molecule, and to Bob Buntrock for the leontine mandelate anecdote.

Soddyite

This is a silicate mineral that was named after Frederick Soddy (1877-1956), the British physicist and radiochemist. In German it's known as Soddyit and it has the formula (UO₂)2SiO₄·2H₂O.

Thanks to Sean Pearce for suggesting this mineral.

Kutnahorite

This is a another mineral that geology students love to mispronounce as "cuttin' a whore right". It's a CaMn(CO₃)₂ mineral originally from Czechoslovakia, and described as a massive and granular material occurring in veins. Its color is almost always some shade of pink, with well-developed cleavage with cleavage surfaces that are commonly curved (aren't they always?).

Thanks to Dave Chapman and Jason Stouffer for suggesting this mineral.

Mucic Acid

Pronounced 'Music acid', this is quite different to Acid Music... This chemical is obtained by the nitric acid oxidation of milk sugar (lactose), dulcite, galactose, quercite and most varieties of gum. It is also called Galactaric Acid. The "mucic acid test" in basic biochemistry lab is a well-known test for D- or L-galactose. The test is carried out by oxidising the sample with concentrated nitric acid; mucic acid crystals will form after leaving the solution overnight. Isn't chemistry great? Just add some acid, and you get some music...

Thanks to Warut Roonguthai for suggesting this molecule.

Burpalite

This mineral with the wonderful name of burpalite, Na₂CaZrSi₂O₇F₂, is named after the Burpala massif in Buryatia, Russia. It sounds a bit like a medicine you give to babies to make them burp...

Thanks to Willem Schipper for suggesting this mineral.

Rhamnetin

This molecule with an amusingly double-entendre name (ram'n it in) actually gets its name from the Buckthorn berry (Rhamnus cathartica), of which it is a derivative. It is a yellow pigment used in the dye industry.

Thanks to Geoff Hallas for suggesting this molecule.

DNA origami

This is a new development in which strands of various lengths of DNA can be 'stitched' together to make nanoshapes. The picture (left) shows AFM images of just some of these shapes (scalebar = 100 nm), including nanostars, and nanosmileys, but you can even write nanomessages using nanoletters and draw nanomaps of the world (see below).

One obvious application of patterned DNA origami would be the creation of a ‘nanobreadboard’, to which diverse components could be added. The attachment of proteins, for example, might allow novel biological experiments aimed at modelling complex protein assemblies and examining the effects of spatial organization, whereas molecular electronic or plasmonic circuits might be created by attaching nanowires, carbon nanotubes or gold nanoparticles.

See: P.W. Rothemund, Nature 440 (2006) 297.

Olympiadane

This molecule consists of five tiny interlocking rings, which mimics the Olympic Games symbol, and so is named 'Olympiadane'. It was first made in 1996, in commemoration of that year's Olympic Games. The successful linkage of these highly complex synthetic molecules means that molecular chains of any length could be constructed with many applications, particularly in the areas of information storage systems and the creation of a 'molecular computer'.

Thanks to Wendy Hunt for suggesting this molecule.

MAP-kinase-kinase-kinase

Mitogen-activated protein (MAP) kinases are proteins that respond to extracellular stimuli (mitogens, e.g. a chemical or protein) and regulate various cellular activities, such as gene expression, mitosis, differentiation, and cell survival or death. As you might expect, a protein that acts upon a MAP-kinase, is called MAP-kinase-kinase. This can go up two more levels, until we have the wonderfully-named 'MAP-kinase-kinase-kinase' - a protein which acts on MAP-kinase-kinase, which acts on MAP-kinase, as a part of intracellular signalling. Now, if another protein were to act on that molecule, I wonder what they'd call it...hmmm

Thanks to Leigh S. Arino de la Rubia for suggesting this molecule.

Coproverdine

This molecule is a new anti-tumor drug that was isolated by the University of Canterbury (Christchurch, New Zealand) from a sponge which was discovered off the coast of New Zealand. In the National Institute for Water and Atmospheric research (NIWA) archives, it is recorded as being "Green-sheep-sh*t like in appearance". The alkaloid they discovered was cytotoxic, but they needed a catchy name for it. They settled on "Coproverdine": Copro - sh*t, Ovis - sheep, and verdi - green.

Thanks to Martin Lee from the University of Canterbury, NZ, for suggesting this molecule, and who apparently spent a year trying to make it!

Labradorite

Labradorite is a silicate mineral that is named after Labrador in eastern Canada, where it was first discovered. Labradorite can produce a colourful play of light across cleavage planes and in sliced sections, called labradorescence, which sounds a bit like a perfume based on the smell of old dogs, or maybe the glow from a radioactive dog! The usually intense colours range from the typical blues and violets through greens, yellows and oranges. The colour display is from lamellar intergrowths inside the crystal.

Thanks to Chris Miller for suggesting this mineral.

'Banana' Borane

This isn't an official name, but I'm told that many chemists who work in the organoborane field use the nickname 'banana borane' to describe molecules such as 9-borabicyclo[3,3,1]nonane, abbreviated BBN. This is because rather than draw out the proper structure (top), they simply draw the borane as a banana shape with the bridging B group sticking out.

Thanks to Rob Saunders for suggesting this fruity molecule.

Skunky Thiol

This molecule is what makes beer taste bad after it's been left exposed to sunlight for a few hours. The actual name is 3-methylbut-2-ene-1-thiol, or 3-MBT for short, but since it's related to molecules found in skunk spray, and it stinks, it's also known as skunky thiol. Only a few nanograms of this thiol in one litre of beer are enough to give the offensive flavour.

Thanks to Matthew Latto for suggesting this smelly molecule. More info: http://www.rsc.org/publishing/journals/PP/article.asp?doi=b609337j

Fartox

On a related theme, this molecule is actually called pentachloronitrobenzene, but goes by a variety of tradenames, including Quintozene, Earthcide and best of all, Fartox. It seems somehow appropriate that Fartox should be a pale yellow solid with a slightly musty odour. It has been used as a soil fungicide since the 1930's, but I have no idea how it came to have this silly name. Maybe it was due to a side-effect of eating fruit sprayed with it?

Dinocap

Dinocap sounds like a dinosaur's hat, or a hat that looks like a dinosaur. It's a dark red viscous liquid that's used to kill mites, fungus and mildew on crops, and goes by the trade name Karathane. There are 2 different versions of dinocap; dinocap-4 is the one shown on the left, and dinocap-6 has the positions of the two blue side-groups swapped. In either case, the liquid is actually a mixture of different isomers, with R₁=CH₃(CH₂)_n and R₂=CH₃(CH₂)_5-n. I'm pretty sure the 'dino-' part of the name comes from 'dinitro-', but the 'cap' remains a mystery.

Naftazone

This sounds like a pretty naff molecule. (For non-UK readers, 'naff' is English slang for poor quality, unfashionable or rubbish). It's used as a drug to protect blood vessels (a 'vasoprotector') - so, maybe it's not quite so naff after all. Its name comes from a contraction of its full name (1,2-naphthoquinone-2-semicarbazone) and has nothing whatsoever to do with the North American Free Trade Agreement (NAFTA).

NUN

This molecule could be habit-forming...It's actually a linear molecule of uranium nitride N-U-N, made by inserting uranium atoms into molecular N₂.

Thanks to Ian for suggesting this pious molecule. More info: R.D. Hunt, J.T. Yustein and L. Andrews, J. Chem. Phys., 98, (1993) 6070.

Discodermolide

Could this be John Travolta's favourite molecule? It's a recently discovered polyketide natural product found to be a potent inhibitor of tumor cell growth, and it gets its name since it was first isolated in 1990 from the Caribbean marine sponge Discodermia dissoluta. Since the compound is light-sensitive, the sponge must be harvested at a minimum depth of 33 metres - so, no disco lighting there then...
An unrelated group of alkaloids isolated from from New Zealand marine sponges are called discorhabdins.  I'm told that groups that work with these compaounds refer to them as 'disco(s)' for short.

More info: Wikipedia. Thanks to Dr Dave Fairley from Singapore for the info about discorhabdins.

Jimthompsonite

This is actually a mineral - a mixture of iron and magnesium silicates, with formula (Mg;Fe²⁺)₅Si₆O₁₆(OH)₂ - that's found in a talc quarry, near Chester, Vermont, USA. It was named after Professor James Burleigh Thompson, Jr., who was an eminent petrologist of Harvard University in the 1940s and 1950s. This is a different Jim Thompson to the one who helped establish the silk industry in Thailand. There's a slightly different version (monoclinic crystal) of this mineral called clinojimthompsonite.

Thanks to David French for suggesting this mineral.

Pregnane

This is a steroid molecule that is the parent compound for many hormones, including the pregnancy hormone progesterone.

Thanks to Vincent Schüler for suggesting this molecule.

Asparagine

I wonder if this molecule tastes of asparagus? In fact it gets its name since it was first isolated in 1806 from asparagus juice, and was the first amino acid to be isolated. It is one of the 20 most common natural amino acids on Earth and can be synthesised in the body. Interestingly, the smell observed in the urine of some individuals after consumption of asparagus is attributed to a byproduct of the metabolic breakdown of asparagine, asparagine-amino-succinic-acid monoamide. However, some scientists disagree and implicate other substances in the smell, especially methanethiol.

Thanks to Vincent Schüler for suggesting this molecule.

Analcite

I thought it was time to show you my analcite! Actually it's a mineral, and although analcite is a valid name for it, it normally goes by the less amusing name of analcime. It's a form of sodium aluminium silicate, and it gets its name from the Greek word meaning 'weak', referring to a weak electrical charge developed on rubbing. So if you rub your analcite, you may get a shock...

Thanks to Daniel Manke of Central Michigan University for suggesting this mineral.

Gingerol

Gingerol isn't the molecule responsible for ginger hair and freckles. Instead, it's the active constituent of fresh ginger. Gingerol is a relative of capsaicin, the compound that gives chilli peppers their spiciness. It's normally found as a pungent yellow oil, but also can form a low-melting crystalline solid. Cooking ginger transforms gingerol into the compound with a 'zing', zingerone.

Thanks to Neil Anderson from Denmark for suggesting this molecule.

Porphyrin Hamburger

A team of researchers at Osaka University, Japan, fused a molybdenum-porphyrin complex and a tungsten polyoxometalate to form a compound they have named the 'porphyrin hamburger'. Two saddle-shaped porphyrin complexes make up the burger buns, while a cluster of tungsten oxide anions surrounding a central silicon cation, known as a polyoxometalate, forms the meat sandwiched between them. The molecules are joined by stable coordination bonds.

This must give plenty of opportunity for derivatives along the lines of Porphyrin Cheeseburger. Or perhaps you could even attach penguinone to make a penguin burger? Or even attach a molecule of cocaine to get a burger and coke?

Thanks to Matt Latto for suggesting this molecule. Original article: A. Yokoyama, T. Kojima, K. Ohkubo, S. Fukuzumi, Chem. Commun., (2007), DOI: 10.1039/b704994c

The porphyrin hamburger: W atoms are shown in pink, O in red, Mo in green, C in grey and N in blue. The central Si ion is shown in dark grey.

Folk Acid

This is nothing to do with folk music, or even acid folk, it is simply a mis-spelling of folic acid, which itself gets its name from the Latin word folium meaning 'leaf'. This seems to be a particlarly common mis-spelling, and occurs even in scientific papers and textbooks (try it on google), maybe a result of word-processing programs automatically 'correcting' words they don't recognise, or just that scientists can't spell.

Thanks to David Bromage from the Australian National University for suggesting this molecule.

PORN

Now that we have the word 'PORN' on this site, it'll either get banned or increase the hit rates hugely! Unfortunately, this PORN is simply the acronym for poly-L-ornithine, a molecule used in cell culture experiments. I suppose that to form a polymer it does involve lots of frantic couplings...so PORN maybe isn't such an inappropriate name after all.

Thanks to Debbie Radtke for suggesting this molecule.

CuNT

This one must be mother of all silly acronyms! Carbon nanotubes are often abbreviated to CNTs, and single-walled ones to SWCNTs. But when a Chinese group recently fabricated copper nanotubes, unbelievably they decided to call them CuNTs! In the same paper they describe bismuth nanotubes, and called them BiNTs. Either they named these 2 structures for a bet - just to see if the Royal Society of Chemistry would publish a paper containing numerous (over 50!) references to BiNTs and CuNTs, or they just didn't realise the meanings of these two acronyms. Or maybe they just did it to increase the number of hits they receive from online searches...

Thanks to Keith Bromley for spotting this paper, which is: D. Yang, G. Meng, S. Zhang, Y. Hao, X. An, Q. Wei, M. Yea and L. Zhang, Chem. Commun., (2007), 1733.

Scorpionate ligands

The scorpionate ligand gets its name from the fact that the ligand can bind a metal with two donor sites like the pincers of a scorpion. The third donor site reaches over the plane formed by the metal and the other two donor atoms to bind to the metal, like a scorpion grabbing the metal with two pincers before stinging it. The most popular class of scorpionates are the tris(pyrazolyl)hydroborates or Tp ligands, and this is shown bonding to a Mn(CO)₃ group, below. Another scorpion-like molecule is bis([1,2]dithiolo)-[1,4]thiazine, which is sometimes unofficially called sscorpionine.

Thanks to Warut Roonguthai for suggesting these two molecules. For more details see: http://en.wikipedia.org/wiki/Scorpionate_ligand, or http://www.chm.bris.ac.uk/motm/sscorpionine/sscorpionine.htm

Puberulin

This wonderfully named molecule gets its name from the fact that it's isolated from the African shrub A. puberula. Hmm, I wonder what you'd measure with a pube-rula...

For more details see: S.A. brown, R.E. March, D.E.A. Rivett, H.J. Thompson, Phytochem. 27 (1988) 391.

Bender's salt

Is this what gay chemists put on their fries? (In the UK, a 'Bender' is a derogatory slang name for a male homosexual). Or maybe it's the salt that Bender from Futurama would use. It's potassium ethylthiocarbonate (C₃H₅KO₂S) and is named after the German Chemist Friedrich Bender.

For more details see: R. Fischer, G. Fessler, Pharmazie. 10 (1955) 349.

Biline

A reporter's favourite molecule? (They always want their by-line). This is a bile pigment, and there are various versions depending upon which nitrogen the H goes (in the diagram it's on N-21, so the molecule shown is 21H-biline), and what side chains (if any) there are.

Blasticidin

And here's one for the military, or maybe just a gung ho chemist (Blast its side in!). It's actually an antibiotic fungicide, and is also used in genetic engineering experiments to fuse pieces of DNA together to make resistant genes.

For more details see: http://www.blasticidin.com/.

Noselite

A superb mineral name, that sounds like just the sort of thing a geologist needs to find his way around ina dark cave. It's a silicate mineral with formula Na₈[SO₄|Al₆Si₆O₂₄], and named after the German mineralogist Karl Wilhelm Nose, and also goes by the name of nosean - as in "I've just been nosean around this rock face". For experiments involving real nose-lights, where the researcher stuck lightbulbs up the noses of volunteers to see how it affected their visual performance, see the wonderfully bonkers paper by N.E. Wetherick (Nature 266 (1977) 442.)

For more details see: http://www.webmineral.com/. Thanks to Peter Rice for the Nature reference.

Brick Acid

'Brick acid' is the nickname given to good old hydrochloric acid (a.k.a. muriatic acid), since it's commonly used by builders to clean up the mortar smudges in brickworks and paving. Some manufacturers sell 'brick acid' as a mixture of 10-30% aqueous HCl with added detergent and sulfuric acid.

Thanks to Michael Buxton for suggesting this molecule.

Pigeonite

Pigeonite is a silicate mineral named after Pigeon Point in Minnesota where it was first found. It forms dark green crystals that are found in volcanic rocks on Earth and in meteorites from Mars or the Moon. Those darn pigeons get everywhere...

Thanks to Dennis J. Walden for suggesting this mineral.

MEAN

MEAN is definitely a mean molecule. It stands for monoethanolamine nitrate, which is an explosive used as a sensitiser in 'slurry explosives' (mixtures of ammonium nitrate, sodium nitrate, a gelling agent and water). Slurry explosives are sometimes used in mining and quarrying, but nowadays they are on various governments' watch-lists as potential terrorist weapons due to their ease of manufacture. I believe it's also used in small quantities as a fertiliser, and doesn't cost too much - so it's a favourite with mean gardeners.

Thanks to Maxime Van den Bossche for suggesting this mean molecule.

Duranterectoside

I'm not sure I like the sound of an 'erectoside'...it sounds like it's a sort of reverse-Viagra! Actually it's a type of glucoside derived from the Japanese plant Duranta erecta. There are several different versions, the one shown is duranterectoside A.

Thanks to Bastiaan Vos for suggesting this molecule. For more details see: Y. Takeda, et al, Phytochem. 39 (1995) 829.

Star Wars 'Tie-Fighter' Molecule

It looks like chemists are trying to outdo each other with making molecules which have weird shapes. This one is described in the paper as being shaped like the Tie-Fighters from the movie Star Wars, and may be used to harvest light in photoelectronic applications. Is this in order to stop everyone going to the dark side...? They are made from a central buckyball with two cyanine 'plates' on each side. Perhaps if many of these were joined together, they could make a light sabre...?

Thanks to Jan Linders for suggesting this molecule. For more details see: F. D'Souza, S. Gadde, M.E. El-Khouly, M.E. Zandler, Y. Araki and O. Ito, J. Porphyrins & Phthalocyanines, 9, (2005) 698, "A supramolecular Star Wars Tie Fighter Ship: electron transfer in a self-assembled triad composed of two zinc naphthalocyanines and a fullerene."

Chitose

This molecule also has the same name as the Japanese city, and is also a common Japanese girl's name. The molecule is a sugar, and gets its name since it's derived from chitin, which comes from the Greek for 'tunic' (chiton). Chitose is one of those molecule names that you have be careful to pronounce, as some people pronounce the 'ch' as 'sh', which makes it sound like an unfortunate toilet accident.

Thanks to FengJun for suggesting this molecule.

Whisky Lactone

Whisky lactone, also known as β-methyl-γ-octalactone or quercus lactone (from the Latin for oak tree Quercus alba), is a flavouring found in American bourbon whiskies, and is also found in all types of oak. The flavour gets into the whisky when it's matured in oak barrels. The pure molecule has a fierce, strong, and sweet smell and can be dissolved in alcohol in any proportion.

Thanks to Charles Turner for suggesting this molecule. See: L. Poisson, P. Schieberle, J. Agric. Food Chem. 56 (2008) 5820.

Ranasmurfin

Ranasmurfin has nothing to do with the blue cartoon Smurfs from Belgium. But it is blue! It's an unusual blue protein isolated from the nests of a Malaysian tree frog, Polypedates leucomystax. During mating, the female produces a protein-rich fluid that she and the male frog, whip up into a sticky foam nest containing the fertilized eggs. These nests exhibit a variety of colours - when first formed they are usually pale creamy white/orange, but frequently develop a darkblue/green color within a few hours or days. This blue colour is due to the protein ranasmurfin.

Thanks to Jan Linders for suggesting this protein. See: M. Oke, et al, Angew. Chem. Int. Ed. 47, (2008) 7853.

Bottle-brush polymers

Bottlebrush compounds are usually polymers in which the main chain adopts an extremely stiff conformation, which is surrounded by expanded but still flexible side chains, thus making the molecules resemble the bottle-brushes used for cleaning test-tubes and, er, bottles, in any chemistry lab.

Thanks to Jan Linders for suggesting this polymer. See: M. Wintermantel, et al, Macromolecules 29, (1996) 978.

Top: A bottlebrush polymer. Bottom: A real bottle brush

Morpholino

A Morpholino sounds like an expensive type of coffee available at Starbuck's ("I'll have a cappucino and my wife will have a morpholino, no sugar"). In fact, Morpholinos are synthetic molecules which result from a redesign of natural nucleic acid structures. They are usually 25 bases in length and they bind to complementary sequences of RNA and modify gene expression. The word "morpholino" can occur in other chemical names, referring to chemicals containing the 'morpholine' ring (shown in the picture). To help avoid confusion between the 2 types of molecules with the same name, when describing the nucleic acid version "Morpholino" is often capitalized. Because of the amine group, morpholine is a base, and it's commonly added in ppm concentrations in power plant steam systems to adjust the pH. Its conjugate acid is given the wonderful name 'morpholinium', e.g. in the salt morpholinium chloride.

See: J. Summerton and D. Weller, Antisense & Nucleic Acid Drug Development (1997) 7 187

Studtite and Metastudtite

Studtite isn't the glue which keeps tongue-studs into place, nor is it the secret formula for Hollywood male actors. It's actually a uranium mineral containing peroxide of formula (UO₂)O₂·4(H₂O) formed by the radioactive decay of nuclear fuel or uranium ores. It occurs as white yellow needle-like crystals, and as a mineral it was named for Franz Edward Studt, a English prospector and geologist who was working in the Belgian Congo.

Thanks to Charles Turner for suggesting this mineral. For more info, see webmineral.com.

N-Confused Porphyrins

If you thought chemistry was confusing, here's your proof - even the molecules are confused! "N-confused" porphyrins are so named because instead of have 4 N's in the central core, they have 2 or 3, making them asymmetrical. These rings, often called 'mutated porphyrins', are not planar, but are twisted. The core H's can flip from one N to another, making the molecule twist and change shape. No wonder they're confused...

Thanks to Joannes T.M. Linders for suggesting this confused molecule. For more info, see J.L. Sessler, Angew. Chem., Int. Ed. Engl. 33 (1994) 1348.

Clintonioside

Staying on the presidential theme, clintonioside is not a molecule specially designed to rid the world of the Clintons. It's a steroidal glycoside extracted from the East Asian plant Clintonia udensis. According to the paper below, the rhizomes of this plant have long been used in traditional Chinese medicine for the treatment of fatigue and 'blow' - which is most appropriate given Bill Clinton's past history...

Thanks to Joannes T.M. Linders for suggesting this molecule. For more info, see Y. Mimaki, K. Watanabe, Helvetica Chimica Acta 91 (2008) 2097.

HAMLET

If you take normal α-lactalbumin (see structure, right), and chemically treat it so it folds up in a specific way, you can change it to be (or not to be?) lethal to cancer cells. Thus, we get HAMLET, human alpha-lactalbumin made lethal to tumor cells. So, as the great man said: "Diseases desperate grown, By desperate appliance are relieved, Or not at all." - William Shakespeare, Hamlet, 4.3.

Thanks to Joannes T.M. Linders for suggesting this literary molecule. For more info, see M. Svensson, A. Håkansson, A.-K. Mossberg, S. Linse, and C. Svanborg, P.N.A.S. 97 (2000) 4221, or the superbly titled paper "Who Is Mr. HAMLET?", E.L. Knyazeva, V.M. Grishchenko, R.S. Fadeev, V.S. Akatov, S.E. Permyakov, and E.A. Permyakov, Biochem, 47 (2008) 13127.

α-lactalbumin
"The devil hath power To assume a pleasing shape." - William Shakespeare, Hamlet, 2.2.

Abyssomicin

Abyssomicins are a class of antibiotics that were found in marine creatures that were collected from a depth of 289 m below the surface of the Sea of Japan. This habitat, 'the Abyss', decisively influenced the naming of this class of natural product, which became known as abyssomicins. Different versions were given different code letters, B, C (shown left), D, etc, but curiously, the letter A was left out of the naming, as if that privilege was reserved for an important compound yet to be discovered from the same source.

Thanks to Joannes T.M. Linders for suggesting this molecule. For more info, see "Discoveries from the Abyss: The Abyssomicins and Their Total Synthesis", K.C. Nicolaou, S.T. Harrison, J.S. Chena, Synthesis, (2008).

Poster from the movie "The Abyss".

Elephantin

There are a whole bunch of naturally occurring sesquiterpenes that have been isolated from the plant Elephantopus elatus Bertol (a.k.a. 'Tall Elephantsfoot' or 'Florida Elephant's-Foot'), and which have been given the prefix 'elephant-' as a result. There's elephantin (structure shown in the picture), elephantol, elephantopin, and dihydroelephantolide. Most of the compounds are cytotoxic and have antileukemic activity. I bet chemists have great fun ordering a flask to do reactions with this compound: "Can I have a round-bottomed flask?" "How big?" "Big enough to fit an elephatin!"

Thanks to J.J. Keating for suggesting these molecules. For more info, see: S.M. Kupchan et al, J. Org. Chem. 34 (1969) 3867.

Persinol

Here's another molecule - and this time it's persinol ! Persinol (structure, right) is a a flavanone derived from the Asian-African herb Aerva persica and is believed to have anti-oxidant properties. A similarly named, but completely different, molecule is persin, which comes from a variety of Guatemalan avocados (Persea americana). This toxic chemical causes damage to the mammary tissues of animals that eat the leaves of this avocado plant, stopping milk production.

Thanks to Kay Dekker for suggesting these molecules. For more info, see: E. Ahmed et al, Arch. Pharm. Res. 29 (2006) 343, and Toxic plants and other natural toxicants by T. Garland and A. C. Barr (CABI, 1998), Chapter 19.

Fawcettimine

Unfortunately, this molecule was not named after Charlie's Angel's star Farrah Fawcett Majors. Instead it was named this way because it was isolated from the Jamaican moss Lycopodium fawcetti.

Thanks to Jan Linders for suggesting these molecules. For more info, see: X. Ma and D.R. Gang, The Lycopodium alkaloids, Nat. Prod. Rep. (RSC, 2004), or J. Org. Chem. 1989, 54, 1548.

Pimpinellin

Pimpinellin sounds like the smooooothest of all molecules... or, alternatively, one that forces other molecules to interact with other molecules. In fact it is a furocoumarin extracted from the roots of the cow parsnip plant. It is thought to be phototoxic, so that if someone ingests this molecule, they become sensitive to light. The molecule probably gets its name from the plant genus Pimpinella, from which I assume it was first isolated (can anyone let me know if that's correct?).

Thanks to Christian Pierce for suggesting this molecule.

Micrococcin

The antibiotic micrococcin is a potent growth inhibitor of the human malaria parasite. It gets its name since it's obtained from a bacterium of the genus Micrococcus isolated from sewage. Apparently, male chemists synthesising this molecule are often very reticent to talk about their work for some reason... Maybe it's because they keep getting asked if they've managed to get their micrococcin yet.

Thanks to Frank Moffatt for suggesting this molecule.

Siamese Twin Molecules

In nature, peptide molecules often cyclise into rings. Sometimes these rings are doubled, with a portion of each ring being shared by each partner. Owing to the resulting proximity of both structurally identical cycles, they have been called 'Siamese depsipeptides', since they resemble conjoined twins or 'Siamese' twins. Two examples made from the starting peptide sansalvamide (SA) are shown in the diagram on the right, where the bold bonds indicate the shared atoms.

Thanks to Jan Linders for suggesting these molecules. Ref: Angew. Chem. Int. Ed. 2009, 48, 8564.

NanoPaNTS, Nanokebabs and Nanodumbbells

Nanopants sound like the clothing required for the Nanoputians we saw earlier. And are nanokebabs what they eat when coming home from the nanopub late at night, just in time for them to do a workout with their nanodumbbells? In fact both these 'molecules' are combinations of nanotubes and nanoparticles. NanoPaNTs are nanotubes that have had metallic nanoparticles attached to their ends using magnetic fields. They can give rise to dumbbell-like structures as shown left. Again using magnetic fields, nanotubes can be made to curl back on themselves to make rings, and straight nanotubes can be threaded through these to make shish-kebab-like structures, as shown right. If you think I'm making all this up, check the reference below...

Thanks to Tim Harrison for suggesting these molecules. Ref: J.G. Duque, et al, J. Phys. Chem. C (2009) 113, 18863.

Diketene

Diketene should really have a hyphen to make it read di-ketene, but without the hyphen it could be pronounced 'dike-tene' - the favourite molecule of lesbian teenagers? Its name in Dutch is 'diketeen', which sounds like 'dikke teen', which means a fat toe!

Thanks to Henk Bosch for suggesting this molecule. Ref: wikipedia.

Carmoterol

This is a drug being developed for asthma treatment by an Italian Pharmaceutical company. The only problem is the name - if you were an asthmatic, would you like to inhale something that sounds like 'car motor oil'?

Thanks to Chris Hall for suggesting this molecule.

Fagomine and Fagarine

Hmm, it's difficult to make any jokes about these molecule names with being very politically incorrect. But we'll do it anyway. :-) Maybe 'fagomine' is how you'd describe a rent-boy to a friend. Since 'fag' in the UK is simply slang for cigarette, saying to someone "would you like a fagomine" is quite innocent. But don't try this in the US... Fagomine was first extracted from buckwheat seeds (Fagopyrum esculentum Moench) and has possible uses to treat diabetic disorders. A related compound with another excellent name, Isofagomine tartrate, is an experimental drug for the treatment of certain forms of Gaucher's disease.
Although sharing a similar-sounding name, fagarine, on the other, hand was extracted from a completely different plant, Argentinian Fagara coco (Rutaceae), and is a potential cardiac drug, although it sounds like a gay figurine.

Thanks to Arnold Martelli for suggesting thes molecules. Ref: A. Kato et al., J. Nat. Prod., (1997) 60 312; V. Deulofeu et al., Nature, 162, (1948) 694.