List of chemical compounds with unusual names

Chemical nomenclature, replete as it is with compounds with complex names, is a repository for some very peculiar and sometimes startling names. A browse through the Physical Constants of Organic Compounds in the CRC Handbook of Chemistry and Physics (a fundamental resource) will reveal not just the whimsical work of chemists, but the sometimes peculiar compound names that occur as the consequence of simple juxtaposition. Some names derive legitimately from their chemical makeup, from the geographic region where they may be found, the plant or animal species from which they are isolated or the name of the discoverer.

Some are given intentionally unusual trivial names based on their structure, a notable property or at the whim of those who first isolate them. However, many trivial names predate formal naming conventions. Trivial names can also be ambiguous or carry different meanings in different industries, geographic regions and languages.

Godly noted that "Trivial names having the status of INN or ISO are carefully tailor-made for their field of use and are internationally accepted".^[1] In his preface to Chemical Nomenclature, Thurlow wrote that "Chemical names do not have to be deadly serious".^[2] A website in existence since 1997^[3] and maintained at the University of Bristol lists a selection of molecules with silly or unusual names strictly for entertainment. These so-called silly or funny trivial names (of course depending on culture) can also serve an educational purpose. In an article in the Journal of Chemical Education, Dennis Ryan argues that students of organic nomenclature (considered a dry and boring subject) may actually take an interest in it when tasked with the job of converting funny-sounding chemical trivial names to their proper systematic names.^[4]

The collection listed below presents a sample of trivial names and gives an idea how chemists are inspired when they coin a brand new name for a chemical compound outside of systematic naming. It also includes some examples of systematic names and acronyms that accidentally resemble English words.

Elements

Glenn Seaborg told his students that he proposed the chemical symbol Pu (from P U) instead of the conventional "Pl" for plutonium as a joke, only to find it officially adopted.^[5] Unununium (Uuu) was the former temporary name of the chemical element number 111, a synthetic transuranium element. This element was named roentgenium (Rg) in November 2004.

Compounds

Name based on shape

Barrelene	(C8H8), the name derives from the resemblance to a barrel.[6]
Basketane	(pentacyclo[4.4.0.02,5.03,8.04,7]decane) (C10H12), a polycyclic alkane with a structure similar to a basket.[3]
Churchane	A polycyclic alkane named for looking superficially like a church.[3]
Cubane	A hydrocarbon whose eight carbon atoms occupy the vertices of a cube.[7]
Dodecahedrane	A Platonic hydrocarbon shaped like a dodecahedron.
Fenestrane	A class of compounds with a 'window pane motif' (the name fenestrane derives from the Latin word fenestra, meaning window), comprising four fused carbocycles centred on a quaternary carbon resulting a twice over spiro compound. The illustration at right shows a generic fenestrane as well as the specific examples [4,4,4,4]fenestrane and [5,5,5,5]fenestrane. Fenestranes are of considerable interest in theoretical chemistry though comparatively few have actually been synthesised.
Housane	A polycyclic alkane named "housane" due to looking superficially like a house.[3]
Ladderane	An organic molecule that looks like a ladder because it contains two or more fused rings of cyclobutane.
Olympiadane	A mechanically-interlocked compound based on the topology for the Olympic rings.
Olympicene	Refers to the fused 5-benzene rings, C19H11, which is reminiscent of the Olympic Flag.[8]
Penguinone	3,4,4,5-tetramethylcyclohexa-2,5-dienone; a two-dimensional representation of its structure resembles a penguin.
Prismane	An isomer of benzene with the carbon atoms arranged in the shape of a triangular prism.
Quadratic acid	A square-shaped organic compound, also called squaric acid.
Tetrahedrane	A Platonic hydrocarbon shaped like a tetrahedron.

Named after people

Buckminsterfullerene	Or buckyballs, a form of carbon named after Buckminster Fuller due to its resemblance to Fuller's geodesic domes. The term was coined by Harold Kroto.[9] The alternative name Footballene was coined by A.D.J. Haymet[10] because the molecule also resembles a football.[3]
Bullvalene	(tricyclo[3.3.2.02,8]deca-3,6,9-triene) (C10H10), was named by organic chemist Maitland Jones, Jr. for William "Bull" Doering who predicted its properties in 1963.[11][12] Within a specific temperature range the molecule is subject to rapid degenerate Cope rearrangements with the result that all carbon atoms and hydrogen atoms are equivalent and that none of the carbon–carbon bonds is permanent.
Dickite	(Al2Si2O5(OH)4), a clay-like material with a number of manufacturing uses, one of which is as a coating for high-quality bond paper. It is named after its discoverer, Dr. W. Thomas Dick.[3]
Josiphos	A well-known catalyst, named after Josi Puleo, the technician who first prepared it.[13] Mandyphos and Taniaphos also exist.

Named after fictional characters

Sounding like vulgarisms

Arsole	(C4H5As), an analogue of pyrrole in which an arsenic atom replaces the nitrogen atom.[16] The aromaticity of arsoles has been debated for many years.[17] The compound in which a benzene ring is fused to arsole — typically on the carbon atoms 3 and 4 — is known as benzarsole.[3]
Bastardane	A close relative to adamantane and its proper name is ethano-bridged noradamantane. Because its unusual ethano-bridge was a deviation from the standard hydrocarbon caged rearrangements, it came to be known as bastardane—the unwanted child.[3][18]
Crapinon	An anticholinergic drug, one side effect of which is constipation.[3]
Cumene	The common name for isopropylbenzene; derived from cumin (Cuminum cyminum)
Cummingtonite	((Mg,Fe)7Si8(OH)22), a magnesium-iron silicate hydroxide, first identified in Cummington, Massachusetts.[3]
DAMN	Diaminomaleonitrile, a cyanocarbon that contains two amine groups and two nitrile groups bound to an ethylene backbone.
DuPhos	A class of asymmetric ligands for asymmetric synthesis. The name DuPhos is derived from the chemical company that developed this type of ligand (DuP, DuPont) and the compound class of phospholanes (Phos) it belongs to.
Earthcide, or Fartox	(C6Cl5NO2), also called Quintozene, some of the many names for pentachloronitrobenzene, a fungicide.[19]
Fucitol	(C6H14O5), an alcohol derived from Fucus vesiculosis, a North Atlantic seaweed. Its optical isomers are also called D-fuc-ol and L-fuc-ol.[3]
fucK	The name of the gene that encodes L-fuculokinase, an enzyme that catalyzes a chemical reaction between L-fuculose, ADP, and L-fuculose-1-phosphate.[3]
Fukalite	(Ca4Si2O6(CO3)(OH, F))2, a rare form of calcium silicocarbonate mined in the Fuka region of Japan.[3]
Ru(Tris)BiPy-on-a-stick	Shorthand form of (trans-1,4-bis[(4-pyridyl)ethenyl]benzene)(2,2'-bipyridine)ruthenium(II).[20]
Pizda	A substance first synthesized by a group of Australian chemists. In some Slavic countries, the word pizda is a vulgarism for "vagina" (see Appendix:Proto-Slavic/pizda).

Related to sex

Fornacite	A rare lead, copper chromate arsenate hydroxide mineral (Pb2CuCrO4AsO4OH), named after its discoverer, Lucien Lewis Forneau.[3]
Orotic acid	Pyrimidinecarboxylic acid has been referred to as vitamin B13. Often misspelled "erotic acid".[3]
Rhamnetin	A flavonol dye derived from buckthorn (rhamnus).[21]
SEX	An abbreviation of sodium ethyl xanthate,[22] it has structural formula CH3CH2OCS2Na, IUPAC name sodium O-ethylcarbonodithioate, and it is a flotation agent used in the mining industry;
Spermine, Spermidine, or polyamine	growth factors involved in cellular metabolism.[3]

Related to body (mal)functions

BARF	(tetrakis[3,5-bis(trifluoromethyl)phenyl]borate), a fluoroaryl borate B(Ar(CF3)2)4−, used as a non-coordinating anion[23]
catP	The name of the enzyme responsible for chloramphenicol resistance in various species of bacteria.
Constipatic acid	[2-(14-hydroxypentadecyl)-4-methyl-5-oxo-2,5-dihydrofuran-3-carboxylic acid], an aliphatic acid derived from the Australian Xanthoparmelia lichen.[3][24]
Nonanal	(C9H18O), an aldehyde derived from nonane.
Uranate	The chemical term for an oxyanion of the element uranium.[3]
Uranocene	U(C8H8)2, a uranium sandwich compound similar to ferrocene (Fe(C5H5)2) with two co-ordinating aromatic and anionic cyclooctatetraenide rings sandwiching the U atom (formally in its +IV oxidation state).
Vomitoxin	A mycotoxin occurring in grains.[3]

Related to death and decay

Cadaverine	A foul-smelling diamine produced by putrefaction of dead animal tissue.[3][25]
DEAD, DEADCAT	An apt acronym, given that diethyl azodicarboxylate is explosive; shock sensitive; carcinogenic; and an eye, skin, and respiratory irritant.[3]
Putrescine	A foul-smelling diamine produced by the putrefaction of dead animal tissue.[3]

Related to religion or legend

Angelic acid	An organic acid found in garden angelica (Angelica archangelica), Umbelliferae, and many other plants.
Diabolic acid	A series of long-chain dicarboxylic acids with chains of different lengths. Named after the Greek word diabollo meaning to mislead.[26]
Draculin	An anticoagulant found in the saliva of vampire bats.[27]
Miraculin	A glycoprotein found in Miracle Fruit that makes sour foods taste sweet after contact with taste buds.[28]

Sounds like a name (person, brand or organization)

Adamantane	(tricyclo[3.3.1.13,7]decane), a crystalline cycloalkane,[29][30] an isomer of twistane. Name resembles that of English pop star Adam Ant.[3]
Irene	Hantzsch-Widman nomenclature for a monocyclic, heterocyclic compound with three ring atoms.[31]
Naftazone	(C11H9N3O2), a vasoprotective drug. The NAFTA free-trade zone is the area covered by the North American Free Trade Agreement.[32]
PEPPSI	PEPPSI is short for Pyridine-Enhanced Precatalyst Preparation Stabilization and Initiation.[33]

A part sounds like an English word

Bongkrek acid	Name sounds like the English names for bong, crack cocaine, and lysergic acid diethylamide.
Complicatic acid	A sesquiterpenoid antibiotic derived from Stereum complicatum, this is also known as dehydrohirsutic acid.[34]
Germane	The simplest hydride of germanium, analogous to methane and silane.
Germanic acid	(Ge(OH)4), the hydrated form of germanium dioxide
HeH+	Chemical formula of the helium hydride ion, a polyatomic ion containing the noble gas helium.[35]
Hirsutene	[36][37] Is also named after an animal, a goat (Hircus).
Jesterone	A ketone with molecular formula C15H20O4 derived from the endophytic fungus Pestalotiopsis jesteri. [38]
Magic acid	A superacid consisting of a mixture, most commonly in a 1:1 molar ratio, of fluorosulfuric acid (HSO3F) and antimony pentafluoride (SbF5).
Megaphone	A ketone derived from the root of Aniba megaphylla.[39]
Moronic acid	[3-oxoolean-18-en-28-oic acid], a natural triterpene
Mucic acid	A product of nitric acid oxidation of galactose or galactose-containing compounds
Muscovite	A phyllosilicate mineral of aluminium and potassium.
Noggin	A signalling protein involved in embryonic development.
Performic acid	A strongly oxidizing acid related to formic acid.
Periodic acid	Or per-iodic acid, is pronounced /ˌpɜr.aɪˈɒdɨk/ PURR-eye-OD-ik and not */ˌpɪərɪˈɒdɨk/ PEER-ee-OD-ik. It refers to one of two interconvertible species: HIO4 (metaperiodic acid), or H5IO6 (orthoperiodic acid - illustrated at right). The per- prefix in the name denotes that iodine is present in its highest possible (+VII) oxidation state.
Picket Fence Porphyrin	(5,10,15,20-tetrakis(alpha,alpha,alpha-2-pivalamidophenyl)porphyrin), used to model heme enzyme active sites.
Piranha solution	A strongly oxidizing mixture of hydrogen peroxide and sulfuric acid used to remove organic residues from substrates and glassware. The name refers to the voracious appetite of the Amazonian piranha fish.
Psicose	(C6H12O6), a rare low-calorie sugar that provides 0.3% as much energy as sucrose.
Rednose	A sugar derived from the degradation of rudolphomycin.[14]
Rhamnose	A sugar naturally occurring in buckthorn (rhamnus).
Sillimanite	Aluminium silicate polymorph, sounds like "Silly man-ite"
Titanic acid	The hydrated form of titanium dioxide.
Traumatic acid	A substance occurring in plants, with a role in healing damaged tissue.

Other

Carbonite	(CO22−), an unstable anion and carbene derived from carbonous acid.
Dinocap	(C18H24N2O6), a miticide and contact fungicide used to control powdery mildew in crops.
Fluoboric acid	(HBF4), tetrafluoroborate or tetrafluoroboric acid.
Homocubane	Any molecule synthesized from cubane.
Methionylthreonylthreonylglutaminylarginyl...isoleucine	The IUPAC name for Titin. This is the largest known protein and so has the longest chemical name. Written in full, it contains 189,819 letters.[40]
Periplanone B	A pheromone of the female American cockroach. Named after the scientific name of this species, Periplaneta americana, not because of periplanarity.
Thebacon	Dihydrocodeinone enol acetate, an opioid analgesic or antitussive.
FOOF	Dioxygen difluoride, O2F2, an extremely unstable compound which reacts explosively with most other substances – the nickname "FOOF" is a play on its formula.
Furfural	Furfural is an industrial chemical compound derived from a variety of agricultural byproducts, including corncobs, oat and wheat bran, and sawdust. The name furfural comes from the Latin word furfur, meaning bran, referring to its usual source.[3]
Gossypol	A toxin found in cottonseed used as a male oral contraceptive.[3]
HArF	chemical formula of argon fluorohydride, the only known neutral compound of the noble gas argon.[41]

See also

• International Union of Pure and Applied Chemistry
• IUPAC nomenclature

Notes and references

Bibliography