Arsole

Yes, believe it or not, there is actually a molecule called Arsole... and it's a ring! It is the arsenic equivalent of pyrrole, and although it is rarely found in its pure form, it is occasionally seen as a sidegroup in the form of organic arsolyls. For more information, see the paper with probably the best title of any scientific paper I've ever come across: "Studies on the Chemistry of the Arsoles", G. Markl and H. Hauptmann, J. Organomet. Chem., 248 (1983) 269. Although the class of molecules with this general structure are called 'arsoles', the specific molecule shown on the right is actually called 'arsenole' (not to be confused with the London football club, Arsenal). Contrary to popular belief, new research (see reference below) shows that arsoles are only moderately aromatic... Incidentally US patent number US 3 412 119 by the Dow Chemical Company is entitled 'Substituted Stannoles, Phospholes, Arsoles, and Stiboles' - I didn't know there was a substitute for an arsole...
Furthermore, if six of them are bonded together we can apply the prefix 'sexi', to get 'sexiarsole'. And the structure where arsole is fused to a benzene ring is called 'benzarsole'; 6 of these bonded together would be called 'sexibenzarsole' (although neither of those sexi- molecules have been synthesised yet). Another well known poisonous arsenic molecule is the simple hydride, called 'arsine', with formula AsH₃.
And on a related theme, I've been told of an Aryl Selenide compound with the superb shorthand of ArSe, which is both toxic and smelly. The paper it comes from in J. Am. Chem. Soc. was published by authors from, of course, the University of Aarhus!
Also, the related molecule phosphole (which just replaces As with P) is quite amusing if you are a French speaker, since it's pronounced the same as 'fausse folle'. Fausse means 'fake' or 'false', and folle means both a 'crazy woman' and a 'drag-queen' or 'ladyboy'.

Thanks to Neil Brookes, Nicholas Welham, Andy Shipway, Lloyd Evans, Peter Sims, John Perkins and Bob Buntrock for some of the info and details about these molecules. This article inspired Mikael Johansson from Helsinki University to do a scientific study into the aromaticity of arsoles, which has been published: Letts. Org. Chem. 2 (2005) 469. Another intriguing reference supplied by Patrick Wallace is: G. Märkl and H. Hauptmann, "Unusual Substitution in an Arsole Ring", Angew. Chem. Int. Ed. . 11, (1972) 441. Thanks also to Thomas Jeanmaire and Alan Parker for the info and translation about phosphole.

Adamantane

This molecule always brings a smile to the lips of undergrads when they first hear its name, especially in the UK. For those not in the know, Adam Ant was an English pop star in the early 1980's famous for silly songs and strange make-up. Adamantane actually gets its name from the Greek adamas meaning 'indestructible', since it's the chemical building block of diamond.

Bastardane

This is actually a close relative of adamantane, and its proper name is ethano-bridged noradamantane. However because it had the unusual ethano bridge, and was therefore a variation from the standard types of structure found in the field of hydrocarbon cage rearrangements, it came to be known as bastardane - the "unwanted child".

[A. Nickon and E.F. Silversmith, 'Organic Chemistry: The Name Game', Pergamon, 1987].

Buckminster Fullerene

This is the famous soccerball-shaped molecule that won its discoverers the Nobel prize for Chemistry in 1996. It is named after the architect Buckminster Fuller who designed the geodesic dome exhibited at Expo '67 in Montreal, from which Sir Harry Kroto got the idea how 60 Carbon atoms could be arranged in a perfectly symmetrical fashion. Because the name of the molecule is a bit of a mouthful, it is often referred to just as a Bucky Ball. It's also known as 'Footballene' by some researchers. In fact, there is now a whole 'fullerene zoo', with oddly coined names, including: Buckybabies (C₃₂, C₄₄, C₅₀, C₅₈), Rugby Ball (C₇₀), Giant Fullerenes (C₂₄₀, C₅₄₀, C₉₆₀), Russian Egg or Bucky Onions (balls within balls), Fuzzyball (C₆₀H₆₀), Bunnyball (C₆₀(OsO₄)(4-t-Butylpyridine)₂), Platinum-Burr Ball ({[(C₂H₅)₃P]₂Pt}₆C₆₀) and Hetero-fullerenes (in which some Cs are replaced by other atoms).
There is also a fullerene paper in which the authors describe a method for severing two adjacent bonds in C₆₀, entitled "There Is a Hole in My Bucky".

Thanks to A. Haymet for the info regarding footballene, and to Charles Turner for the names of the other fullerenes which came from: 'Fullerenes', by Robert F. Curl and Richard E. Smalley, Scientific American October 1991, and to Tom Hawkins for the JACS reference.

Megaphone

Despite having a ridiculous name, the molecule is quite ordinary. It gets its name from being both a constituent of Aniba Megaphylla roots and a ketone.

[S.M. Kupchan et al, 'J. Org. Chem.', 43 (1978) 586].

Munchnones

No, these aren't the favourite compound of the Munchkins from The Wizard of Oz, but are in fact a type of mesoionic compound. These are ring structures in which the positive and negative charge are delocalised, and which cannot be represented satisfactorily by any one polar structure. They got their name when Huisgen called them after the city Munich (München), after similar compounds were called sydnones after Sydney.

Huisgen et al. Chem. Ber. 1970, 103, 2611. Thanks to Matthew J. Dowd, Virginia Commonwealth University, Richmond, VA, for supplying this one.

Unununium

I know this is technically an element, not a molecule, but it had such a ridiculous name I thought I'd include it. This is actually element number 111, and was called by the IUPAC temporary systematic name of unununium before it was recently renamed roentgenium. This is a pity, because if it formed ring or cage structures, previously we might have ended up with unununium onions...

[See Pure and Appl. Chem. 51 (1979) 381 for the naming scheme]. Thanks to Chris Fellows for info about its new name.

A sample of pyroxmangite, with white pieces of cummingtonite visible toward the lower left.

Cummingtonite

This mineral must have the silliest name of them all! Its official name is magnesium iron silicate hydroxide, and it has the formula (Mg,Fe)₇Si₈O₂₂(OH)₂. It got its name from the locality where it was first found, Cummington, Massachusetts, USA.

Putrescine, Cadaverine, Spermine and Spermidine

Putrescine originates in putrefying and rotting flesh, and is quite literally, the smell of death. It is one of the breakdown products of some of the amino-acids found in animals, including humans. Although the molecule is a poisonous solid, as flesh decays the vapour pressure of the putrescine it contains becomes sufficiently large to allow its disgusting odour to be detected. It is usually accompanied by cadaverine (named after the cadavers that give rise to it), a poisonous syrupy liquid with an equally disgusting smell. Putrescine and cadaverine also contribute towards the smells of some living processes. Since they are both poisonous, the body normally excretes them in whatever way is quickest and most convenient. For example, the odour of bad breath and urine are 'enriched' by the presence of these molecules, as is the 'fishy' smell of the discharge from the female medical condition bacterial vaginosis. Putrescine and cadaverine also contribute to the distinctive smell of semen, which also contains the related molecules spermine and spermidine.

Thanks to Bill Longman for suggesting spermine and spermidine, and to Dr Chris Valentine for the info about bacterial vaginosis.

Silly names, and smelly too...
(3D structure files:
putrescine, cadaverine, spermine, spermidine)

2 layers of dickite.

Dickite

Dickite, Al₂Si₂O₅(OH)₄, is a (kaolin) clay-like mineral which exhibits mica-like layers with silicate sheets of 6-membered rings bonded to aluminium oxide/hydroxide layers. Dickite is used in ceramics, as paint filler, rubber, plastics and glossy paper. It got its name from the geologist that discovered it around the 1890s, Dr. W. Thomas Dick, of Lanarkshire, Scotland.

Structure from the Virtual Museum of Minerals and Molecules

Moronic Acid

This is a triterpenoid organic acid that is found in Pistacia resin, and is therefore of interest to people studying archaeological relics, shipwrecks and the contents of ancient Egyptian jars. Its name comes from its corresponding hydroxy acid, which was originally named morolic acid since it was isolated from the heartwood of the mora tree, mora excelsa. The keto acid then became moronic acid. Derivatives of this are called moronates, as in 'which moron-ate the contents of this jar?'

Ref: P.L. Majumdar, R.N. Maity, S.K. Panda, D. Mal, M.S. Raju and E. Wenkert, J. Org. Chem. (1979) 44, 2811.
Thanks to Dr Ben Stern of Bradford University for supplying this one,and to John Perkins for the story of the name origin.

Moronic acid

Curious Chloride and Titanic Chloride

The trivial name for some curium compounds can be either curous or 'curious', so curium trichloride becomes curious chloride. However the only curious property it has is that it's sufficiently radioactive that a solution, if concentrated enough, will boil spontaneously after a while. (I wonder if a molecule with 2 Cm atoms in would be 'bi-curious'...?)
In a similar way, titanium compounds can be 'titanic', so we get the wonderfully named titanic chloride, TiCl₄. It's also interesting to know that in the titanium industry, TiCl₄ is known as 'tickle'. Furthermore, curium oxides are called 'curates', so the titanium compound would be Titanic Curate, and since curium can have more than one valency we could end up with Curious Curates. But I'm sure these are already a well-known phenomenon...
In a similar way, some nickel compounds can be referred to as 'nickelous' - so we get compounds like Nickelous Sulfate (a nice guy by all accounts...)

Thanks to Beveridge and Dr Justin E. Rigden for supplying these two and to John Burgess and Neil Tristram for the ideas on curates, and to Michael Geyer for the Nickelous content.

Fukalite

This wonderfully named mineral gets its name from the Fuka mine in the Fuka region of southern Japan. It is very rare, and is a form of calcium silico-carbonate, with formula Ca₄Si₂O₆(CO₃)(OH,F)₂.

More details from: Henmi, C., Kusachi, I., Kawahara, A., and Henmi, K., Mineral. J.,8, (1977) 374. Thanks to Matthew Latto for info on this mineral.

Traumatic Acid

This is a plant hormone which causes injured cells to divide and help repair the trauma - hence its name, and its synonym 'wound hormone'.

Thanks to Dr Neil Edwards for supplying this one, and to Han Wermaat in the Dutch Chemistry magazine 'Chemisch2weekblad' for its information.

Arabitol

No, this has nothing to do with rabbits - it's an organic alcohol that's one constituent of wine. It's also known as pentahydric alcohol. A related sugar molecule, arabinose, also has nothing to do with rabbits, nor with the size of a Rabbi's nose (A Rabbi Nose).

Thanks to David Brady for supplying info about arabitol, and to Darren Sydenham for arabinose.

Fucitol

Although this sounds like what an undergraduate chemist might exclaim when their synthesis goes wrong, it's actually an alcohol, whose other names are L-fuc-ol or 1-deoxy-D-galactitol. It gets its wonderful trivial name from the fact that it is derived from the sugar fucose, which comes from a seaweed found in the North Atlantic called Bladderwrack whose latin name is Fucus vesiculosis. Interestingly, there are a few articles in the Journal of Biochemistry throughout 1997 concerning a kinase enzyme which acts on fucose. The creators of these articles were Japanese, and seemed to have missed the fact that fucose kinase should not be abbreviated as 'fuc-K'. Similarly, the E. coli K-12 Gene has other proteins that have been named Fuc-U and Fuc-R.

Thanks to Bob Brady for suggesting this one, and to Dr Stephen O'Hanlon from the Orthopaedics Dept of Bedford Hospital for the information on fucose kinase, and to Professor Anthony Davis of Bristol University for suggesting FucU and FucR.

Erotic Acid

No, this isn't the world's best aphrodisiac. Its correct name is orotic acid, but it has been misspelt so often in the chemical literature that it is also known as erotic acid! Another name for it is vitamin B13. Apparently, if you add another carbon to it, it becomes homo-erotic acid...

Thanks to Gerard J. Kleywegt of Uppsala University for info on this molecule.

Kinoshitalite

Although it sounds like the trade name of a laxative, this is a type of mica found in Japan and Sweden, and has the formula (Ba,K)(Mg,Mn)₃Si₂Al₂O₁₀(OH)₂. It is green and vitreous, and is about as hard as fingernails, apparently. Its name comes from the Japanese for "under the tree" (ki = tree; no = possessive particle; shita = under).

Thanks to Van King for info on this mineral and Melita Rowley for the Japanese translation.

Bastadin-5

This is just one of a number of bastadins, which are molecules isolated from the marine sponge Ianthella basta. They possess antibacterial, cytotoxic and anti-inflammatory properties.

Thanks to Neil Edwards for info on this molecule.

Vomicine

This poisonous molecule gets its name from the nut Nux Vomica, which is the seed of a tree found on the coasts of the East Indies. The seeds are sometimes called 'Quaker buttons', and are a source of strychnine as well as the emetic vomicine.

Thanks to Bill Longman and Alan Howard Martin for info on this molecule.

Rhamnose

This sounds like the molecule that's created when you walk into doors...in fact it's a type of sugar.

Thanks to Bill Longman for info on this molecule.

Gossypol

This ridiculously named molecule is found in cotton seeds. It was used as a male contraceptive in China, but was never used in the West (and may have since been banned in China as well), since its effects were permanent in about 20% of patients! Its name originated from being present in the flowers of the Indian cotton plant Gossypium herbaceum L. Apart from its contraceptive effects, gossypol has properties that might make it useful in treating a number of ailments, including cancer, HIV, malaria and some bacterial/viral illnessness. Related to this molecule are the equally strangely named gossypetin and gossypin. I always thought 'gossypin' was frowned upon in polite labs...

Thanks to Lionel Hill for suggesting this molecule, and to Anthony Argyriou and Kristina Turner for providing some of the info.

Skatole

This molecule's name comes from 'skatalogical', meaning concerning fecal material. Its proper name is 3-methylindole, but it gets its trivial name from the fact that it is a component of feces. Surprisingly, it is also found in coal tar and beetroot (!), and can be obtained synthetically by mixing egg albumin and KOH. Skatole consists of white crystals when pure (or brownish scales when impure) which are soluble in hot water. Apparently, coriander can be used to cover up bad smells such as these, as testified in the classic paper: "Deodorizing Effect of Coriander on the Offensive Odor of the Porcine Large Intestine" [Kohara et al, Food Sci. Technol. Res. 12 (2006) 38.]

Thanks to Allen Knutson for suggesting this molecule, and to Samuel Knight for providing the info.

Arsenolite

This is a naturally occurring mineral, whose correct name is cubic arsenic trioxide (As₂O₃). It is also the primary product whenever arsenic ores are smelted, and is used in industry as a glass decolourising agent. Another related mineral with a similar silly name is arsenolamprite, which is a native form of arsenic.

Thanks to Matthew Latto and Nicholas Welham for suggesting these minerals.

Sexithiophene

This is a 'sexi' molecule - which means it has 6 sub-units, in this case of thiophene rings. Because of its conjugated system of double bonds, this organic molecule conducts electricity quite well. As a result, it is one of a number of similar molecules being studied for possible uses in organic polymer electronics. Incidentally, the Latin for 5 sub-units is quinque (pronounced 'kinky'), so by adding one subunit a quinque molecule becomes sexi... Nine units would be nonakis...which shows what always happens if you try to take things too far.

Bis(pinacolato)diboron

Although it sounds like it, this isn't the active ingredient in a pina colada cocktail. Rather it is a versatile reagent for the preparation of boronic esters from halides, the diboration of olefins, and solid-phase Suzuki coupling. A proper Pina Colada cocktail is a concoction of pineapple juice, coconut milk and rum, often served with crushed ice and a little paper umbrella stuck in the glass.

Thanks to Victoria Barclay of Advanced Chemistry Development, Inc., Toronto, for providing the info on this molecule. More info: Tet. Letts. 39 (1998) 2357.

Lucifer yellow

I think Lucifer Yellow is a food colouring used especially in hot sauces, like salsa pickle. It is also used in plant microscopy anatomy studies, because it fluoresces under ultraviolet light and stains certain regions between plant cells.

For more info, see here. Thanks to Gavin Shear of Advanced Chemistry Development, Inc., Toronto, and to Seranne Howis, of Rhodes University, South Africa, for providing the info on this molecule.

Crapinon

Crapinon (also known as Sanzen) is another molecule with an excellent name, and is apparently used therapeutically as an anticholinergic. These are drugs which dry secretions, increase heart rate, and decrease lung constriction. More importantly, they also constipate quite strongly - so 'crappy-non' is most appropriate. It would be nice to think that this molecule could find an alternative use as a toilet cleaner (as in "Who's been crapinon the seat?").

Thanks to Gavin Shear of Advanced Chemistry Development, Inc., Toronto, and to Tom Simpson of the Royal Hobart Hospital, Austalia for providing the info on this molecule.

Sparassol

This molecule sounds like what you'd need the day after eating a very hot curry (spare-assol). Sparassol is an antibiotic produced by the fungus Sparassis ramosa.

Thanks to Eric Walters from The Chicago Medical School for providing the info on this molecule.

Periodic Acid

Ok, I know it should really be per-iodic acid, but without the hyphen it sounds like it only works some of the time...It has also been described as that acid extracted by boiling of old periodic tables found in chemistry lecture halls and laboratories.

Thanks to Allen Knutson for suggesting this molecule, and to Prof Walter Maya of California State Polytechnic University for some of the details.

Phthalic Acid

This molecule is often pronounced with a silent 'th' for comic effect. I wonder if phthalyl side-groups have a shorthand symbol in chemical structures, in the same way that phenyl groups are shortened to -Ph? If so, would it be a 'phthalic symbol'...?
Again, adding an extra carbon makes homo-phthalic acid - say no more...

Thanks to Neil Edwards for info about this molecule.

Psicose

This molecule has nothing to do with axe-murderers, but is a sugar which gets its name because it's isolated from the antibiotic psicofurania. Its other name is ribo-hexulose.

Commic Acid

This molecule's always good for a laugh! It gets its 'commical' name since it's a constituent of the plant Commiphora pyracanthoides, one of the Myrrh trees. When reduced to the aldehyde, I presume the product would be named commical?

Thanks to Michael F Aldersley for info about this molecule.

Fruticolone

This sounds like what you get after a baked bean meal...but it actually gets its name from being both a constituent of the plant Teucrium fruiticans and a ketone.

Nonanone

Although maybe not quite as silly as some of the other molecular names, I like this one for its n-n-nice alliteration. Many nonanones act as alarm pheremones in wasps, ants and bees. Interestingly, in Danish, Norwegian, Swedish and German molecular names are spelt without the end "e" (e.g. butane is butan, etc.). Therefore nonanone becomes 'nonanon', and is quite an exceptional molecule name, being spelled the same way forwards and backwards - a palindromic molecule! The molecule shown is 2-nonanone, but 5-nonanone with the C=O group in the middle would be the same forward as well as backwards, thus being palindromic in spelling and in structure!

Thanks to Carl Kemnitz for supplying some info about this molecule.

Fukugetin

This chemical with a most amusing name is also called Morellofavone, and is a constituent of the bark of the Garcenia species of tree. Its glucoside goes by the equally wonderful name of Fukugiside.

Pubescine

Also known as Reserpinine. It got its name since it was extracted from the plant Vinca pubescens. I don't know much else about pubescine, but I bet it forms short, curly crystals...

Thanks to Michael J. Mealy of the University of Conneticut and to ShadowFox for providing the info on this molecule.

Spamol

Monty Python's favourite molecule? Spamol might also conjure images of unwanted "Make Money Fast" emails circulating the globe at the speed of light ("spam - all"). Its other names are aminopromazine, lispamol or lorusil, and it's actually used as an anti-spasmodic therapeutic agent.

Thanks to Victoria Barclay of Advanced Chemistry Development, Inc., Toronto, for providing the info on this molecule.

Fukiic Acid

Fuki is the Japanese word for the butterbur flower, and Fukiic acid is the hydrolysis product from this plant, Petasites japonicus. Interestingly, further oxidation of this produces the wonderfully named Fukinolic acid. (I wonder if fukanolic is anything like alcoholic...) Anyway, since the conjugate base of fukinolic acid is fukinolate, it's probably about time we stopped!

Thanks to Anton Sherwood for info on fukiic acid, and to Andrew Reinders for suggesting fukinolate.

Funicone

This gets its name, not from being funny and cone shaped, but because it's the metabolism product of the fungus Penicillium funiculosum.

Housane, Churchane and Basketane

Obviously, these molecules get their name from their shapes. Although I do think that housane (how sane?) should be closely linked to psicose, above.

Thanks to A. Rich for suggesting these molecules.

Windowpane

Windowpane C₉H₁₂ gets its name from its resemblance to a set of windows, and is more accurately kown as fenestrane. But unfortunately it has never been synthesised. However, the version with a corner carbon missing C₈H₁₂ has been made, and goes by the name 'broken window'. Interestingly, a hypothetical derivative of windowpane has been suggested which includes a double bond, and this would of course be called Windowlene...

Thanks to Adrian Davis of Pfizer Global Research & Development for providing the info on these molecules, and to Iain Fenton for suggesting windowlene.

Godnose

Ok, so this is a bit of a cheat, since it's not an official molecular name...but it makes a nice story. When Albert Szent-Gyorgyi isolated ascorbic acid and published his findings, he called the new substance 'ignose' since he was convinced it was a sugar that resembled glucose and fructose, but was ignorant of its structure. When the journal editor refused to accept ignose as a sensible name, Szent-Gyorgyi suggested 'Godnose' instead! Alas the editor was neither imaginative nor humorous, and suggested that a more proper name had to be used. The structure of the carbohydrate was elucidated in collaboration with Haworth at Birmingham and the alternative name given was hexuronic acid (hex = six). During the same period (1928–1931), Charles Glen King of the Columbia University of USA isolated Vitamin C from lemon juice and it was observed that hexuronic acid and Vitamin C were identical. Szent-Györgyi documents the episode in the essay "Lost in the Twentieth Century" which dates from 1963.

Thanks to John P Oliver, Peter Macinnis and Charles Turner for providing the info and story. Incidentally, Godnose is also the name of an Australian punk band.

Luciferase

This molecule is an enzyme which reacts with ATP to cleave luciferin, its substrate. This cleavage reaction causes the firey glow in fireflies and certain types of fish, hence its name.

Thanks to Melissa Harrison for suggesting this molecule.

Diabolic Acid

Diabolic acids are actually a class of compounds where the m and n chains can have different lengths and can contain unsaturation. They were named after the Greek diabollo, meaning to mislead, since they were particularly difficult to isolate using standard gas chromatography techniques. One of the inventors, Prof Klein, also thought that they had 'horns like the devil'.

Domperidone

This molecule sounds like it should be the active ingredient in Dom Perignon champagne, but it's actually an anti-emetic drug. It is also used to promote the production of breast milk in lactating (or non lactating women). It's also been used to induce lactation in a male!

Thanks to Eric Walters from The Chicago Medical School for suggesting this molecule, and to Liz Parnell for some info about it.

Gardenin

If you fancy a bit of gardenin', this is the molecule for you. In fact, these are many different gardenins, which are flavones extracted from Gardenia lucida, a plant from India. The structure left is for gardenin A, which forms yellow crystals.

Thanks to Eric Walters from The Chicago Medical School for suggesting this molecule. Ref: A.V.R. Rao, et al, Indian J. Chem. 8 (1970) 398.

Germane

This is a particularly relevant molecule that is pertinent and has a bearing on a number of inorganic reactions...

Thanks to Eric Walters from The Chicago Medical School for suggesting this molecule.

Uranate

Kunzite (Spodumene)

This mineral is a pink (of course...) gemstone, named after the gemologist G.F. Kunz who described it in 1902. Kunzite is a fragile stone, which shows different shades of colour when viewed from different directions. Called an "evening" stone, it should not be exposed to direct sunlight which can fade its color in time. Its alternative name, Spodumene, sounds like an American shop that sells computer nerds ("Spod-U-Mean")

Conantokin

This chemical sounds like Conan the Barbarian has been smoking something he shouldn't... In fact it's a peptide neurotoxin found in the marine snail Conus geographus. Researchers have found that some conantokins cause young mice to fall asleep, and older mice to become hyperactive, but they don't say what happens to middle-aged mice...It probably gets its name because it was isolated from Conus snails hence "con-". And, "antok" is a Filipino word which means "sleepy", which refers to its effect on young mice. Apparently, there is also a related molecule called "contulakin". "Tulak" is a Filipino term for "push". It seems that this molecule causes mice to be sluggish and thus, they had to be pushed.

Thanks to Dr. Andrew P. Rodenhiser from McGill University, Canada, for suggesting this molecule, and to Jesper Karlsson of the University of Kalmar, Sweden, and Rene Angelo Macahig of Ateneo de Manila University, Philipines, for more info about it.

Welshite

This wonderfully named mineral is called after the US amateur mineralogist Wilfred R. Welsh. Its formula is Ca₂SbMg₄FeBe₂Si₄O₂₀. Some people think it's quite a nice mineral, but others think it's 'well-shite'.

Thanks to Matthew Latto for suggesting this mineral.

Propellane and Cubane

These two molecules are both named after their distinctive shapes. Propellane (left), C₅H₆, resembles a propeller, whereas cubane (right), C₈H₈, is a cube (but doesn't come from Cuba). Other molecules that get their name from their geometric shapes are: dodecahedrane C₂₀H₂₀, prismane C₆H₆, spherands and hemispherands, squaric acid C₄H₂O₄ and deltic acid C₃H₂O₃, tetrahedranes C₄H₄ and C₂₀H₃₆ and finally twistane C₁₀H₁₆.

Thanks to Kay Brower for suggesting propellane, and to Martin A. Iglesias Arteaga from the University of Havana, Cuba for suggesting cubane. Thanks also to Mark Minton for suggesting the other list of geometrical molecules. First reference for propellane: J. Altman , E. Babad, J. Itzchaki, D. Ginsburg , Tetrahedron, Suppl. 8(1), (1966) 279.

Clitoriacetal

This gets its name from the root of the Clitoria macrophylla plant, and is a constituent of the Thai drug "Non-tai-yak" which is used to treat respiratory disorders, including pulmonary tuberculosis and bronchitis, and also works as an insecticide.

Vaginatin

I know you can get most things nowadays in a tin, but this is getting silly... Actually it gets its name from the plant Selinum Vaginatum. The related molecule is Vaginol, which also goes by the name Archangelicin.

Thanks to Matti.Lepisto and Stephen Yabut for the info on this molecule.

Anol

Anol is a synonym for 4-(1-propenyl)phenol, and it is apparently used in the flavour industry. Are compounds that bond strongly to this molecule called 'anolly retentive'?

Thanks to Phil Van Es for suggesting this molecule.

Urospermal

The European Union has standardised everything else (apple sizes, the shapes of bananas, etc...) and it now sounds like they're going even further (Euro-sperm-all). In reality, it gets its name from being a constituent of the roots of the Urospermum delachampii plant.

Buccalin

This sounds like the molecule from which car seat-belts are made, but it's actually a neuropeptide which acts in nerves to stop acetylcholine release.

Thanks to Dr. Andrew P. Rodenhiser from McGill University, Canada, for suggesting this molecule.

Antipain

Antipain is a protease inhibitor, which means it prevents proteins from being degraded. Despite its promising name, it is a very toxic compound, and it causes severe itch or pain (!) when contacted with the skin. Its name is actually a contraction of anti-papain, since it inhibits the action of papain, an enzyme found in papayas.

Thanks to Marcel Volker from Leiden University Medical Center, Netherlands, for suggesting this molecule.

Dinile

Why did the two cyanide groups go to see a psychiatrist? Because they were both 'in dinile'... In fact, dinile is another name for butanedinitrile or succinonitrile, and is a waxy solid that if ingested forms cyanides in the body.

Thanks to Hazel Mottram and Phil van Ess for suggesting this molecule.

Fornacite

This is a mineral that is composed of a basic chromate-arsenate compound of Pb and Cu with the formula: (Pb,Cu²⁺)₃[(Cr,As)O₄]₂(OH). If it could be polished into a gemstone, it sounds ideal for a ring that a cheating husband might buy his mistress.

Thanks to Alan Plante, a New Hampshire, USA, "Rockhound", for suggesting this mineral.

The dark lumpy bits on the white background are Fornacite

Butanal

This molecule sounds better if it's hyphenated (but-anal), but it is actually quite a common aldehyde.

Thanks to Shawn McClements, Amsterdam NY, USA, and his high school class for suggesting this molecule.

Angelic Acid

Angelic acid isn't very angelic at all - it's a defence substance for certain beetles. It gets its name from the Swedish plant Garden Angelica (Archangelica officinalis) from whose roots it was first obtained in the 1840s. Its proper name is (Z)-2-methyl-2-butenoic acid. The other isomer (E) goes by the equally silly name of tiglic acid (from the plant Croton tiglium, the source of croton oil) and is also a beetle defence substance.

Thanks to Andrew Walden for suggesting these molecules and to Florian Raab and Bo Ohlson for providing some of the information about them.

Ciglitizone

This molecule sounds like the places reserved for smokers to light up. Actually, ciglitizone is is a member of a class of compounds that are used as anti-diabetics. The drug Avandia (Rosiglitazone), used to treat type II diabetes, is a member of this class of compounds. Another related molecule is troglitazone, which I've mentioned for all fans of the eponymous rock group or small cave dwelling dwarfs.

Thanks to Robin Brown of Galapagos Genomics, Belgium, and to Joerg Fruechtel for the info on this molecule. (More info, see: Br. J. Pharmacol. 131 (2000) 651).

Clitorin

I don't know much about clitorin, except that it's a flavenol glycoside (make of that what you will), but I've heard it's touch sensitive ;-).

Thanks to Joerg Fruechtel and Nicholas J. Welham for the info on this molecule. (More info, see: Chem. Pharm. Bull. 53 (2005) 591).

Constipatic Acid

This is a constituent of some Australian lichens, such as Parmelia constipata. I don't know why these lichens were called this, maybe eating them causes constipation? Derivatives of constipatic acid include protoconstipatic acid, dehydroconstipatic acid, and methyl constipatate.

See D.O. Chester and J.A. Elix, Austr. J. Chem. 32 (1979) 2565. Thanks to Ronald Wysocki of the University of Arizona for suggesting this molecule.

Fucol

This sugar sounds like it doesn't do very much! Actually the L-Fucol form is obtained from the eggs of sea urchins, frog spawn and milk. The L-fucol form also goes by the name of rhodeose.

Thanks to Ronald Wysocki of the University of Arizona for suggesting this molecule.

Penguinone

This gets its name from the similarity of its 2D structure to a penguin. The effect is slightly lost in the 3D model, though. It's real name is: 3,4,4,5-tetramethylcyclohexa-2,5-dienone.

Thanks to Chris Scotton for suggesting this molecule.

Ovalene

Ovalene is a polycyclic aromatic hydrocarbon, C₃₂H₁₄. Funnily enough it's oval-shaped... In the series of polycyclic aromatic hydrocarbons to which ovalene belongs, the next one is circumanthracene...(is it also known as oy-vane?).

Thanks to Terry Frankcomb of the University of Queensland, Australia for suggesting this molecule, and to Professor Juan Murgich of the Venezuelan Institute for Scientific Research, Caracas, for providing a correct structure.

Aenigmatite

This mineral gets its 'enigmatic' name from the fact that its chemical composition was originally difficult to determine. It is an iron and titanium silicate with sodium as a charge balancing cation, although because it does not easily fit into the current classification system, it is classified as an 'Unclassified Silicate'.

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

Dogcollarane

Dogcollaranes are a group of molecules made from alternating bicyclo [2,2,0] and norbornyl segments. When there are 24 such components, the ends can be linked together to form a ring, which looks like a dogcollar. Unfortunately, although many of the intermediate structures have been made, none of the dogcollaranes have yet been synthesised.

For more info, see: Aust. J. Chem. 40 (1987) 1951.
Thanks to John Lambert of the University of Melbourne for suggesting this molecule.

Fuchsite

Fuchsite is a mineral, and is the green form of Muscovite, KAl₂(AlSi₃O₁₀)(F, OH)₂. It is used as an ornamental stone, and apparently has perfect cleavage...

Thanks to Tanuki for suggesting this mineral.

Sepulchrate and Sarcophagene

These spooky sounding molecules both have structures which wrap around and enclose metal atoms, such as cobalt, in a coffin-like cage. Hence their names.

Thanks to Mark Minton for suggesting this molecule.

Pagodane

This C₂₀H₂₀ molecule gets its name because it resembles a Japanese pagoda - well, two pagodas, back-to-back.

Thanks to Mark Minton for suggesting this molecule.

DEAD

DEAD is actually the acronym for diethyl azodicarboxylate, which is an important reagent in the well-known Mitsunobu reaction which performs a stereospecific conversion of an alcohol to a primary amine. It's quite a good acronym, as DEAD is an orange liquid that's explosive, shock sensitive, light sensitive, toxic, a possible carcinogen or mutagen, and an eye, skin and respiratory irritant! A version of diethyl azodicarboxylate mixed with acid and triphenylphosphine has also been termed DEADCAT.

Thanks to 'Sparkly' Sally Ewen for suggesting this molecule.

Apatite

A mineral for hungry people? Apatite is a phosphate mineral with the composition Ca₅[PO₄]₃(OH,F,Cl). It has been used extensively as a phosphorus fertilizer and is still mined for that purpose today. The mineral called "asparagus stone" is a appropriately a type of green apatite. Ironically, apatite is the mineral that makes up the teeth in all vertebrate animals as well as their bones.

Thanks to 'Sparkly' Sally Ewen for suggesting this molecule and to Sean and to Kay Dekker for some info about it.

Lepidopterene or Biplanene

Lepidopterenes are a whole class of molecules named after their structural similarity to a butterfly. When the two wings are directly over one another, they look like a WW1 biplane, and so this group of molecules has been termed 'biplanenes'.

Thanks to Mark Minton for suggesting this molecule.

Snoutene

This strange looking molecule resembles the nose or snout of an animal, but I don't know if it smells...

Thanks to Mark Minton for suggesting this molecule.

Crown Ethers and Lariat Ethers

Both these molecules get their names from their distinctive shapes. Crown ethers look like crowns (shown in red in the picture on the right), whereas lariat ethers look like lassos, and are really just crown ethers with extended 'tails' (shown in blue). Some lariat ethers are so flexible that they can stick their tails into their rings (nice trick!), and so have been termed 'ostrich complexes', or 'tail biters'. Lariat ethers with two tails are called 'bibrachial lariat ethers' (bracchium means 'arm'), and are abbreviated as BiBLEs.

Thanks to Mark Minton for suggesting this molecule.

Cacodyl

This molecule gets its name from the Greek kakodes, meaning 'stinking', as it has a really pungent smell of manure with a delicate hint of garlic. It is sometimes spelled 'kakodyl', but its correct name is tetramethyl diarsenic. Its main claim to fame is that it was one of the compounds worked on by Bunsen (of burner fame).

Thanks to Birgit Schulz for suggesting this molecule and to Lars Finsen for correcting the spelling of the name.

Betweenanene (Screwene)

Betweenanenes are molecules which have a trans double bond shared between two cycloalkanes. There is a whole family of them, depending upon the size of each ring. The one shown on the right is the [10,10] betweenanene. If there are two double bonds linked together, the molecules are called screwenes, but this terminology isn't that popular, for obvious reasons!

More info see: J. Am. Chem. Soc. 99 (1977) 3508. Thanks to Mark Minton for suggesting this molecule.

Paddlane

Paddlanes are molecules which have bicyclic cyclohexane units, which look a bit like the paddles on Mississippi steamboats.

Thanks to Mark Minton for suggesting this molecule.

I bet Dr. Michael Hfuhruhurr could use some furfuryl furfurate about now...

Furfuryl Furfurate

A ridiculously-named molecule, about which I know virtually nothing, although I'm told it's quite smelly and may be used as a vapour phase polymerisation inhibitor. It got its name from the Latin "furfur", meaning "bran" (the source of the compound). A related molecule, furfural alcohol is apparently used in the fabrication process of the Reinforced Carbon-Carbon (RCC) sections used in the space shuttle.

Thanks to Steve Colley for suggesting this molecule, and to Calli Arcale and Ogpusatan and Danny Sichel for info about it.

Carnallite

Carnallite is KMgCl₃·6H₂O, an evaporite mineral. Surprisingly for a mineral called carnallite, it doesn't exhibit any cleavage... It's used as an ore for potassium fertilizers, and is named after Rudolf von Carnall, a Prussian mining engineer, whose (Carnall?) knowledge of the subject was famous...

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

Draculin

Draculin is the anticoagulant factor in vampire bat saliva. It is a large glycoprotein made from a sequence of 411 amino acids.

Thanks to Mark Baxter for suggesting this molecule, to Eric Walters for some of the info about it and to Tara Turnas for the molecular structure image.