List of chemical compounds with unusual names

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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[edit]

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[edit]

Name based on shape[edit]

Barrelene
Barrelene
(C8H8), the name derives from the resemblance with 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]
ChurchaneA polycyclic alkane named for looking superficially like a church.[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.
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
Housane.svg
A polycyclic alkane named "housane" due to looking 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.
OlympiceneRefers to the fused 5-benzene rings, C19H11, which is reminiscent of the Olympic Flag.[8]
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.
Tetrahedrane
Tetrahedrane
A Platonic hydrocarbon shaped like a tetrahedron.

Named after people[edit]

Buckminsterfullerene
Fullerene
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
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.[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]
JosiphosA well-known catalyst, named after Josi Puleo, the technician who first prepared it.[13] Mandyphos and Taniaphos also exist.

Named after fictional characters[edit]

AlcindoromycineAn anthracycline antibiotic agent named after the character Alcindoro in La Bohème.[14]
BohemamineAn anti-tumour agent named after the Puccini opera La Bohème.[14]
CollinemycinAn anthracycline antibiotic agent named after the character Colline in La Bohème.[14]
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.[14]
MusettamycinAn anthracycline antibiotic agent named after the character Musetta in La Bohème.[14]
MarcellomycinAn anthracycline antibiotic agent named after the character Marcello in La Bohème.[14]
PikachurinA retinal protein named after Pokémon character / species Pikachu
RudolphomycinAn anthracycline antibiotic agent named after the character Rodolfo (Rudolph) in La Bohème.[14][15]
Sonic hedgehogA protein named after Sonic the Hedgehog

Sounding like vulgarisms[edit]

Arsole
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]
BastardaneA 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]
CrapinonAn anticholinergic drug, one side effect of which is constipation.[3]
Cumene
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
DAMN Structure.png
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
(C6Cl5NO2), also called Quintozene, some of the many names for pentachloronitrobenzene, a fungicide.[19]
Fucitol
L-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]
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 mined in the Fuka region of Japan.[3]
Ru(Tris)BiPy-on-a-stickShorthand form of (trans-1,4-bis[(4-pyridyl)ethenyl]benzene)(2,2'-bipyridine)ruthenium(II).[20]
Pizda
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[edit]

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).[21]
SEXAn 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
Spermine
Spermidine
growth factors involved in cellular metabolism.[3]

Related to body (mal)functions[edit]

BARF
BARF
(tetrakis[3,5-bis(trifluoromethyl)phenyl]borate), a fluoroaryl borate B(Ar(CF3)2)4, used as a non-coordinating anion[23]
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][24]
Nonanal
Nonanal
(C9H18O), an aldehyde derived from nonane.
UranateThe chemical term for an oxyanion of the element uranium.[3]
Uranocene
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
Vomitoxin
A mycotoxin occurring in grains.[3]

Related to death and decay[edit]

Cadaverine
Cadaverine
A foul-smelling diamine produced by putrefaction of dead animal tissue.[3][25]
DEAD
DEAD
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]

Related to religion or legend[edit]

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.[26]
Draculin
Draculin
An anticoagulant found in the saliva of vampire bats.[27]
MiraculinA 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)[edit]

Adamantane
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]
IreneHantzsch-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]
PEPPSIPEPPSI is short for Pyridine-Enhanced Precatalyst Preparation Stabilization and Initiation.[33]

A part sounds like an English word[edit]

Complicatic acidA sesquiterpenoid antibiotic derived from Stereum complicatum, this is also known as dehydrohirsutic acid.[34]
Germane
Germane
The simplest hydride of germanium, analogous to methane and silane.
Germanic acid(Ge(OH)4), the hydrated form of germanium dioxide
HeH+
Helium hydride ion
Chemical formula of the helium hydride ion, a polyatomic ion containing the noble gas helium.[35]
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
Mucic acid
Mucic acid
A product of nitric acid oxidation of galactose or galactose-containing compounds
Muscovite
Muscovite crystals
A phyllosilicate mineral of aluminium and potassium.
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 /ˌpɜr.ˈɒdɨk/ 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 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.
Psicose
Psicose
(C6H12O6), a rare low-calorie sugar that provides 0.3% as much energy as sucrose.
RednoseA sugar derived from the degradation of rudolphomycin.[14]
Rhamnose
Rhamnose
A sugar naturally occurring in buckthorn (rhamnus).
Titanic acidThe hydrated form of titanium dioxide.
Traumatic acid
Traumatic acid
A substance occurring in plants, with a role in healing damaged tissue.

Just sounds silly[edit]

FOOF
Fluorine dioxide.svg
Dioxygen difluoride, O2F2, an extremely unstable compound which reacts explosively with most other substances – the nickname "FOOF" is a play on its formula.[citation needed]
Furfuryl furfurate
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
Gossypol
A toxin found in cottonseed used as a male oral contraceptive.[3]
HArF
Argon fluorohydride
chemical formula of argon fluorohydride, the only known neutral compound of the noble gas argon.[39]
Horseradish peroxidaseAn enzyme used extensively in molecular biology applications primarily for its ability to amplify a weak signal and increase detectability of a target molecule.

Other[edit]

Carbonite(CO22−), an unstable anion and carbene derived from carbonous acid.[citation needed]
Dinocap
Dinocap
(C18H24N2O6), a miticide and contact fungicide used to control powdery mildew in crops.
Fluoboric acid
Fluoboric acid
(HBF4), tetrafluoroborate or tetrafluoroboric acid.[citation needed]
HomocubaneAny molecule synthesized from cubane.
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.[40]
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.[citation needed]
Thebacon
Thebacon
Dihydrocodeinone enol acetate, an opioid analgesic or antitussive.[citation needed]

See also[edit]

Notes and references[edit]

  1. ^ Godly, E.W. (1998). Chemical Nomenclature. Kluwer Academic Publishers. p. 20. ISBN 0-7514-0475-6. 
  2. ^ Thurlow, Kevin (1998). Chemical Nomenclature. Kluwer Academic Publishers. xii. ISBN 0-7514-0475-6. 
  3. ^ a b c d e f g h i j k l m n o p q r s t u v w x y May, Paul (28 May 2013). "Molecules with Silly or Unusual Names". Bristol University. Retrieved 1 November 2013. 
  4. ^ Dennis, Ryan (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. "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. ^ "'Olympic rings' molecule olympicene in striking image". BBC Online. 27 May 2012. Retrieved 28 May 2012. 
  9. ^ Kroto, H.W.; Heath, J.R.; O'Brien, S.C.; Curl, R.F.; Smalley, R.E. Nature, 1985, 318(6042), 162.
  10. ^ Haymet, A.D.J. J. Am. Chem. Soc. 1986, 108, 319.
  11. ^ 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. 
  12. ^ 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. 
  13. ^ 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. 
  14. ^ a b c d e f g h 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.
  15. ^ "Canadian Patents Database CA 1110562: Anthracycline antibiotic designated RUDOLPHOMYCIN". Retrieved 2007-08-16. 
  16. ^ G. Märkl and 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. 
  17. ^ Mikael P. Johansson and Jonas Jusélius (2005). "Arsole Aromaticity Revisited". Lett. Org. Chem. (3): 469–474. 
  18. ^ 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. 
  19. ^ "NIST Standard Reference Database 69, June 2005 Release: NIST Chemistry WebBook - Pentachloronitrobenzene". Retrieved 2007-08-16. 
  20. ^ Toma SH, Uemi M, Nikolaou S, Tomazela DM, Eberlin MN, Toma HE., Inorg Chem. 2004 May 31; 43(11):3521–3527
  21. ^ Uri J, Csoban G, Viragh E., Acta Physiol Hung. 1951;2(2):223-8.
  22. ^ See, for example, N Okibe and DB Johnson, Biotechnology Letters, 2004 24(23), 2011–2016 doi:10.1023/A:1021118915720
  23. ^ "BARF". ChemSpider. Royal Society of Chemistry. 2013. Retrieved 4 November 2013. 
  24. ^ D.O. Chester and J.A. Elix, Australian Journal of Chemistry 32 (1979) 2565-2569 doi:10.1071/CH9792565
  25. ^ NORDENSTROM BE (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. 
  26. ^ R A Klein, G P Hazlewood, P Kemp, and R M Dawson, Biochem J. 1979 December 1; 183(3): 691–700.
  27. ^ 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. PMID 7740503. 
  28. ^ 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. 
  29. ^ Prelog, V., Seiwerth,R. (1941). Berichte 74: 1644 and 1769. doi:10.1002/cber.19410741109. 
  30. ^ Not to be confused with the fictional material adamantium
  31. ^ Parent Hydride Names and Substantive Nomenclature (PDF). IUPAC. March 2004. p. 16. 
  32. ^ 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. 
  33. ^ "PEPPSI Catalysts". Retrieved 2009-04-01. 
  34. ^ T. Money (1975), "Sesquiterpenoids", Terpenoids and Steroids, vol. 5, Royal Society of Chemistry, p. 69, ISBN 9780851862965, ISSN 0300-5992 
  35. ^ Hogness, T.; Lunn, E. (1925). "The Ionization of Hydrogen by Electron Impact as Interpreted by Positive Ray Analysis". Physical Review 26 (1): 44–55. doi:10.1103/PhysRev.26.44. 
  36. ^ Tandem radical approach to linear condensed cyclopentanoids. Total synthesis of (.+−.)-hirsutene Dennis P. Curran and Donna M. Rakiewicz J. Am. Chem. Soc.; 1985; 107(5) pp 1448 - 1449; doi:10.1021/ja00291a077
  37. ^ Isolation, structure and synthesis of hirsutene, a precursor hydrocarbon of coriolin biosynthesis Shigeo Nozoe, Jun Furukawa, Ushio Sankawa and Shoji Shibata Tetrahedron Letters Volume 17, Issue 3 , January 1976, Pages 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. ^ Räsänen, Markku; Khriachtchev, Leonid; Pettersson, Mika; Runeberg, Nino; Lundell, Jan (2000). "A stable argon compound". Nature 406 (6798): 874–876. doi:10.1038/35022551. PMID 10972285. 
  40. ^ Sam Kean (2011), The Disappearing Spoon, Random House, p. 36, ISBN 9781446437650 

Bibliography[edit]