List of chemical compounds with unusual names

Chemical nomenclature, replete as it is with compounds with complex names, is a repository for some names that may be considered unusual. 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
Barrelene
(C8H8), the name derives from the resemblance to a barrel.[6]
Basketane
Basketane
(pentacyclo[4.4.0.02,5.03,8.04,7]decane) (C10H12), a polycyclic alkane with a structure similar to a basket.[3]
Cubane
Cubane
A hydrocarbon whose eight carbon atoms occupy the vertices of a cube.[7]
Dodecahedrane
Dodecahedrane
A Platonic hydrocarbon shaped like a dodecahedron.[8]
Fenestrane
Fenestranes
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" because it looks superficially like a house.[3]
Ladderane
Pentacycloanammoxic Acid
An organic molecule that looks like a ladder because it contains two or more fused rings of cyclobutane.
Olympiadane
Olympiadane
A mechanically-interlocked compound based on the topology for the Olympic rings.
Olympicene
Olympicene
Refers to the fused 5-benzene rings (C19H12), which is reminiscent of the Olympic Flag.[9]
Penguinone
Penguinone
3,4,4,5-tetramethylcyclohexa-2,5-dienone; a two-dimensional representation of its structure resembles a penguin.
Prismane
Prismane
An isomer of benzene with the carbon atoms arranged in the shape of a triangular prism.
Quadratic acid
Squaric acid
A square-shaped organic compound, also called squaric acid.
Sulflower
Sulflower
A stable heterocyclic octacirculene based on thiophene, named as a portmanteau of sulfur and sunflower.

Named after people
Buckminsterfullerene (Fullerene)
Fullerene
Also called the buckyball, this is an allotrope of carbon named after Richard Buckminister Fuller due to its resemblance to Fuller's geodesic domes. The term was coined by Harold Kroto.[10] The alternative name footballene was coined by A.D.J. Haymet[11] because the molecule also resembles a football;[3] the 70-atom version is said to resemble a rugby ball from its own oval shape.
Bullvalene
Bullvalene C10H10
(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.[12][13] 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, Allan Brugh Dick.[14]
Josiphos ligandsA well-known catalyst, named after Josi Puleo, the technician who first prepared it.[15] Mandyphos and Taniaphos also exist.

Named after fictional characters
AlcindoromycineAn anthracycline antibiotic agent named after the character Alcindoro in La Bohème.[16]
BohemamineAn anti-tumour agent named after the Puccini opera La Bohème.[16]
CollinemycinAn anthracycline antibiotic agent named after the character Colline in La Bohème.[16]
RanasmurfinA blue protein from the foam nests of a tropical frog, named after the Smurfs.
MimimycinAn anthracycline antibiotic agent named after the character Mimì in La Bohème.[16]
MusettamycinAn anthracycline antibiotic agent named after the character Musetta in La Bohème.[16]
MarcellomycinAn anthracycline antibiotic agent named after the character Marcello in La Bohème.[16]
PikachurinA retinal protein named after Pokémon character / species Pikachu
RudolphomycinAn anthracycline antibiotic agent named after the character Rodolfo (Rudolph) in La Bohème.[16][17]
Sonic hedgehogA protein named after Sonic the Hedgehog

Sounding like vulgarisms
Arsole
Arsole
(C4H5As), an analogue of pyrrole in which an arsenic atom replaces the nitrogen atom.[18] The aromaticity of arsoles has been debated for many years.[19] The compound in which a benzene ring is fused to arsole — typically on the carbon atoms 3 and 4 — is known as benzarsole.[3]
BastardaneA close relative to tetramantane (a higher homologue of adamantane), its proper name is nonacyclo[11.7.1.112,18.03,16.04,13.05,10.06,14.07,11.015,20]docosane. 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][20]
CrapinonAn anticholinergic drug, one side effect of which is constipation.[3]
Cummingtonite((Mg,Fe2+)2(Mg,Fe2+)5Si8O22(OH)2), 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
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		Some of the many names for pentachloronitrobenzene, a fungicide.[21]
Fucitol
L-Fucitol
(C6H14O5), an alcohol derived from Fucus vesiculosus, a North Atlantic seaweed. Its optical isomers are also called D-fuc-ol and L-fuc-ol.[3]
FucKThe 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 discovered in the Fuka Mine of Takahashi, Japan.[3]
Pizda
Pizda
Abbreviated ligand name of a substance 1-(2’’-hydroxyl cyclohexyl)-3-[aminopropyl]-4-[3’-aminopropyl] piperazine, first synthesized by a group of Australian chemists. In some Slavic countries, the word pizda is a vulgarism for "vagina" (see Reconstruction:Proto-Slavic/pizda).
Ru(Tris)BiPy-on-a-stickShorthand form of (trans-1,4-bis[(4-pyridyl)ethenyl]benzene)(2,2'-bipyridine)ruthenium(II).[22]
FornaciteA rare lead, copper chromate arsenate hydroxide mineral (Pb2CuCrO4AsO4OH), named after its discoverer, Lucien Lewis Forneau.[3]
Orotic acid
Orotic acid
Pyrimidinecarboxylic acid has been referred to as vitamin B13. Often misspelled "erotic acid".[3]
Rhamnetin
Rhamnetin
A flavonol dye derived from buckthorn (rhamnus).[23]
SEXAn abbreviation of sodium ethyl xanthate,[24] a flotation agent used in the mining industry.
Spermine,
Spermidine
Spermine
Spermidine
growth factors involved in cellular metabolism.[3]
BARF
BARF
(tetrakis[3,5-bis(trifluoromethyl)phenyl]borate), a fluoroaryl borate B(Ar(CF3)2)4−, used as a non-coordinating anion[25]
catPThe name of the enzyme responsible for chloramphenicol resistance in various species of bacteria.
Constipatic acid
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][26]
dUMP
dUMP
Deoxyuridine monophosphate, an intermediate in nucleotide metabolism
Nonanal
Nonanal
(C9H18O), an aldehyde derived from nonane.
PoOChemical formula of polonium monoxide.
UranateThe chemical term for an oxyanion of the element uranium.[3]
Vomitoxin
Vomitoxin
A mycotoxin occurring in grains.[3]
Cadaverine
Cadaverine
A foul-smelling diamine produced by putrefaction of dead animal tissue.[3][27]
DEAD, DEADCAT
DEAD
Diethyl azodicarboxylate: An apt acronym, given that diethyl azodicarboxylate is explosive; shock sensitive; carcinogenic; and an eye, skin, and respiratory irritant.[3]
Putrescine
Putrescine
A foul-smelling diamine produced by the putrefaction of dead animal tissue.[3]
Angelic acid
Angelic acid
An organic acid found in garden angelica (Angelica archangelica), Umbelliferae, and many other plants.
Diabolic acidA series of long-chain dicarboxylic acids with chains of different lengths. Named after the Greek word diabollo meaning to mislead.[28]
Draculin
Draculin
An anticoagulant found in the saliva of vampire bats.[29]
Luciferase A generic term for the class of oxidative enzymes that produce bioluminescence.
MiraculinA glycoprotein found in miracle fruit that makes sour foods taste sweet after contact with taste buds.[30]

Sounds like a name (person, brand or organization)
Adamantane
Adamantane
(tricyclo[3.3.1.13,7]decane), a crystalline cycloalkane,[31][32] an isomer of twistane. Name resembles that of English pop star Adam Ant.[3]
IreneHantzsch-Widman nomenclature for a monocyclic, heterocyclic compound with three ring atoms.[33]
Naftazone(C11H9N3O2), a vasoprotective drug. The NAFTA free-trade zone is the area covered by the North American Free Trade Agreement.[34]
PEPPSIPyridine-Enhanced Precatalyst Preparation Stabilization and Initiation.[35]

A part sounds like an English word
Bongkrek acid
Bongkrek acid
Name sounds like a combination of English words related to recreational drugs: bong; crack, a preparation of cocaine; and acid, a street name for lysergic acid diethylamide.
Hirsutene
Hirsutene
[36][37] Is also named after an animal, a goat (Hircus).
Magic acidA superacid consisting of a mixture, most commonly in a 1:1 molar ratio, of fluorosulfuric acid (HSO3F) and antimony pentafluoride (SbF5).
MegaphoneA ketone derived from the root of Aniba megaphylla.[38]
Moronic acid
Moronic acid
[3-oxoolean-18-en-28-oic acid], a natural triterpene
NogginA signalling protein involved in embryonic development.
Performic acidA strongly oxidizing acid related to formic acid.
Periodic acid
Periodic acid
Or per-iodic acid, is pronounced /ˌpɜːraɪˈɒdɪk/ PURR-eye-OD-ik and not */ˌpɪəriˈɒdɪk/ 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 solutionA 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.
RednoseA sugar derived from the degradation of rudolphomycin.[16]
Rhamnose
Rhamnose
A sugar naturally occurring in buckthorn (rhamnus).
SillimaniteAluminium silicate polymorph, sounds like "Silly man-ite"
Traumatic acid
Traumatic acid
A substance occurring in plants, with a role in healing damaged tissue.

Other
Dinocap
Dinocap
(C18H24N2O6), a miticide and contact fungicide used to control powdery mildew in crops.
Homocubane
homocubane
cubane homolog with additional CH2 group, C9H10
Methionylthreonylthreonylglutaminylarginyl...isoleucineThe 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.[39]
Periplanone B
Periplanone B
A pheromone of the female American cockroach. Named after the scientific name of this species, Periplaneta americana, not because of periplanarity.
Thebacon
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.[40]
Gossypol
Gossypol
A toxin found in cottonseed used as a male oral contraceptive.[3]
Melon
Melon

See also

Notes and references
  1. Godly, E.W. (1998). Chemical Nomenclature. Kluwer Academic Publishers. p. 20. ISBN 978-0-7514-0475-3.
  2. Thurlow, Kevin (1998). Chemical Nomenclature. Kluwer Academic Publishers. xii. ISBN 978-0-7514-0475-3.
  3. May, Paul (28 May 2013). "Molecules with Silly or Unusual Names". Bristol University. Retrieved 1 November 2013.
  4. Ryan, Dennis (1997). "Old MacDonald Named a Compound: Branched Enynenynols" (PDF). Journal of Chemical Education. 74 (7): 782. Bibcode:1997JChEd..74..782R. doi:10.1021/ed074p782. Retrieved 2007-08-16.
  5. Glenn T. Seaborg, Citizen-Scholar, By Peggy House, Reprinted from The Seaborg Center Bulletin, April 1999
  6. Zimmerman, Howard E.; Robert M. Paufler (1960). "Bicyclo [2.2.2]octa-2,5,7-triene (barrelene), a unique cyclic six electron pi system". Journal of the American Chemical Society. 82 (6): 1514–1515. doi:10.1021/ja01491a071.
  7. Verbrugge, P. A. (1977). "Unusual organic compounds. XXIV. Compounds with the formula (CH)n. (d). Synthesis of cubane, (CH)8; homocubanes". Chemie en Techniek (Amsterdam). 32 (4): 120–123.
  8. Pubchem. "Dodecahedrane". pubchem.ncbi.nlm.nih.gov. Retrieved 2018-07-28.
  9. "'Olympic rings' molecule olympicene in striking image". BBC Online. 27 May 2012. Retrieved 28 May 2012.
  10. Kroto, H.W.; Heath, J.R.; O'Brien, S.C.; Curl, R.F.; Smalley, R.E. (1985). "C60: Buckminsterfullerene". Nature. 318 (6042): 162. Bibcode:1985Natur.318..162K. doi:10.1038/318162a0. S2CID 4314237.
  11. Haymet, A.D.J. (1986). "Footballene: a theoretical prediction for the stable, truncated icosahedral molecule C60". J. Am. Chem. Soc. 108 (2): 319. doi:10.1021/ja00262a035.
  12. Doering, W. von E.; Roth, W. R. (1963). "A Rapidly Reversible Degenerate Cope Rearrangement : Bicyclo[5.1.0]octa-2,5-diene". Tetrahedron. 19 (5): 715–737. doi:10.1016/S0040-4020(01)99207-5.
  13. Ault, Addison (2001). "The Bullvalene Story. The Conception of Bullvalene, a Molecule That Has No Permanent Structure". J. Chem. Educ. 78 (7): 924. Bibcode:2001JChEd..78..924A. doi:10.1021/ed078p924.
  14. Ross, C.; Kerr, P.F. (1931). "Dickite, a Kaolin Mineral" (PDF). American Mineralogist. 15: 34–39.
  15. Blaser, Hans-Ulrich; Brieden, Walter; Pugin, Benoit; Spindler, Felix; Studer, Martin; Togni, Antonio (2002). "Solvias Josiphos ligands: from discovery to technical applications". Topics in Catalysis. 19 (1): 3–16. doi:10.1023/A:1013832630565. S2CID 95738043.
  16. Nettleton DE Jr, Balitz DM, Doyle TW, Bradner WT, Johnson DL, O'Herron FA, Schreiber RH, Coon AB, Moseley JE, Myllymaki RW, J Nat Prod. 1980 Mar–Apr;43(2):242–258. DOI: 10.1021/np50008a003
  17. "Canadian Patents Database CA 1110562: Anthracycline antibiotic designated RUDOLPHOMYCIN". Archived from the original on 2007-11-14. Retrieved 2007-08-16.
  18. G. Märkl & H. Hauptmann (1983-06-14). "Untersuchungen zur Chemie der Arsole 1,1-dichlor-1-R-λ5-arsole-1-chlorarsole 2,2′,5,5′-tetraphenyldiarsolyl (Studies on the chemistry of arsoles)". J. Organomet. Chem. 248 (3): 269–285. doi:10.1016/S0022-328X(00)98709-6.
  19. Mikael P. Johansson & Jonas Jusélius (2005). "Arsole Aromaticity Revisited". Lett. Org. Chem. (3): 469–474.
  20. Schleyer, Paul von Rague; Eiji Osawa; Michael G. B. Drew (1968). "Nonacyclo[11.7.1.12,18.03,16.04,13.05,10.06,14.07,11.015,20]docosane, a bastard tetramantane" (PDF). J. Am. Chem. Soc. 90 (18): 5034–5036. doi:10.1021/ja01020a053. Retrieved 2007-08-15.
  21. "NIST Standard Reference Database 69, June 2005 Release: NIST Chemistry WebBook – Pentachloronitrobenzene". Retrieved 2007-08-16.
  22. Toma, SH; Uemi, M; Nikolaou, S; Tomazela, DM; Eberlin, MN; Toma, HE (2004). "{trans-1,4-Bis[(4-pyridyl)ethenyl]benzene}(2,2'-bipyridine)ruthenium(II) Complexes and Their Supramolecular Assemblies with β-Cyclodextrin". Inorg Chem. 43 (11): 3521–3527. doi:10.1021/ic0352250. PMID 15154817.
  23. Uri J, Csoban G, Viragh E., Acta Physiol Hung. 1951;2(2):223-8.
  24. See, for example, Okibe, N; Johnson, DB (2004). "Toxicity of flotation reagents to moderately thermophilic bioleaching microorganisms". Biotechnology Letters. 24 (23): 2011–2016. doi:10.1023/A:1021118915720. S2CID 23948075.
  25. "BARF". ChemSpider. Royal Society of Chemistry. 2013. Retrieved 4 November 2013.
  26. Chester, DO (1979). "Three New Aliphatic Acids from Lichens of Genus Parmelia (Subgenus Xanthoparmelia )". Australian Journal of Chemistry. 32 (11): 2565. doi:10.1071/CH9792565.
  27. Nordenström, Björn E. W. (1951). "Effect of cadaverine and lysine on the urinary excretion of piperidine in rabbits". Acta Pharmacologica et Toxicologica. 7 (3): 287–296. doi:10.1111/j.1600-0773.1951.tb02870.x. PMID 14856760.
  28. R A Klein, G P Hazlewood, P Kemp, and R M Dawson, Biochem J. 1979 December 1; 183(3): 691–700.
  29. Apitz-Castro R, Béguin S, Tablante A, Bartoli F, Holt JC, Hemker HC (1995). "Purification and partial characterization of draculin, the anticoagulant factor present in the saliva of vampire bats (Desmodus rotundus)". Thromb. Haemost. 73 (1): 94–100. doi:10.1055/s-0038-1653731. PMID 7740503.
  30. Theerasilp S, Kurihara Y (August 1988). "Complete purification and characterization of the taste-modifying protein, miraculin, from miracle fruit". J. Biol. Chem. 263 (23): 11536–11539. PMID 3403544.
  31. Prelog, V., Seiwerth, R. (1941). "Über eine neue, ergiebigere Darstellung des Adamantans". Berichte. 74 (11): 1769–1772. doi:10.1002/cber.19410741109.CS1 maint: multiple names: authors list (link)
  32. Not to be confused with the fictional material adamantium
  33. Parent Hydride Names and Substantive Nomenclature (PDF). IUPAC. March 2004. p. 16.
  34. Charles O, Coolsaet B (1972). "[Prevention of hemorrhage in prostatic surgery. Apropos of the study of the hemostatic activity in prostatectomy of a new molecule: beta-naphthoquinone monosemicarbazone (Naftazone)]". Annales d'Urologie (in French). 6 (3): 209–212. PMID 4562066.
  35. "PEPPSI Catalysts". Retrieved 2009-04-01.
  36. Curran, Dennis P. (1985). "Tandem radical approach to linear condensed cyclopentanoids. Total synthesis of (.+-.)-hirsutene". Journal of the American Chemical Society. 107 (5): 1448–1449. doi:10.1021/ja00291a077.
  37. Nozoe, Shigeo (1976). "Isolation, structure and synthesis of hirsutene, a precursor hydrocarbon of coriolin biosynthesis". Tetrahedron Letters. 17 (3): 195–198. doi:10.1016/0040-4039(76)80013-5.
  38. SM Kupchan, KL Stevens, EA Rohlfing, BR Sickles, AT Sneden, RW Miller, RF Bryan, J. Org. Chem., 43(4) (1978) 586
  39. Sam Kean (2011), The Disappearing Spoon, Little, Brown, p. 36, ISBN 9781446437650
  40. Derek, Lowe (2010-02-23). "Things I Won't Work With: Dioxygen Difluoride". In the Pipeline. Retrieved 2019-04-02.

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