List of chemical compounds with unusual names

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]


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.

Godley 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 classic 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.

Adamantane (tricyclo[3.3.1.13,7]decane), a crystalline cycloalkane.[5] [6]
Alcindoromycine an anthracycline antibiotic agent named after the character Alcindoro in La Bohème.[7]
Arsole (C4H5As), an analogue of azole in which an arsenic atom replaces the nitrogen atom.[8] The aromaticity of arsoles has been debated for many years.[9] Such a replacement in a benzene ring, where the arsenic atom replaces a carbon atom, is known as benzarsole
BARF (tetrakis[3,5-bis(trifluoromethyl)phenyl]borate)
Barrelene (C8H8), the name derives from the obvious resemblance with a barrel.[10]
Bastardane a close relative to adamantane and its proper name is ethano-bridged noradamante. Because its unusual ethano-bridge was a variation from the standard hydrocarbon caged rearrangements, it came to be known as bastardane—the unwanted child.[11]
Bohemamine an anti-tumour agent named after the Puccini opera La Bohème.[7]
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.[12] The alternative name Footballene was coined by A.D.J. Haymet[13] because the molecule also resembles a football (soccer ball).
Cadaverine a foul-smelling diamine produced by putrefaction of dead animal tissue.[14]
Cinnamaldehyde C9H8O the compound which gives cinnamon its flavor.[15]
Collinemycin an anthracycline antibiotic agent named after the character Colline in La Bohème.[7]
Constipatic acid [2-(14'-hydroxypentadecyl)-4-methyl-5-oxo-2,5-dihydrofuran-3-carboxylic acid], an aliphatic acid derived from the Australian Xanthoparmelia lichen.[16]
Crapinon an anticholinergic drug, one side effect of which is constipation
Cubane a hydrocarbon whose eight carbon atoms occupy the vertices of a cube.[17]
Cummingtonite ((Mg,Fe)7Si8(Template:Hydroxide)22), a magnesium-iron silicate hydroxide, first identified in Cummington, Massachusetts.
Diabolic acid a series of long-chain dicarboxylic acids with chains of different lengths. Named after the Greek word diabollo meaning to mislead.[18]
DEAD an apt acronym, given that diethyl azodicarboxylate is explosive; shock sensitive; carcinogenic; and an eye, skin, and respiratory irritant.
Dickite (Al2Si2O5(Template:Hydroxide)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.
Dinocap (C18H24N2O6), a miticide and contact fungicide used to control powdery mildew in crops.
Draculin an anticoagulant found in the saliva of vampire bats.[19]
Earthcide or Fartox or 'Quintozene, two of the many names for pentachloronitrobenzene, a fungicide.[20]
Fenestrane The parent of a class of compounds based on the window pane motif
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.
Fluoboric Acid BF4H, tetrafluoroborate or tetrafluoroboric acid.
Fukalite (Ca4Si2O6(Template:Carbonate)(Template:Hydroxide,F))2, a rare form of calcium silicocarbonate mined in the Fuka region of Japan.
Gossypol a toxin found in cottonseed used as a male contraceptive.
Hirsutene [21] [22] is also named after an animal: a goat (Hircus), occasionally the molecule is depicted upside down [23] [24]
Irene Hantzsch-Widman nomenclature for a monocyclic, heterocyclic compound with three ring atoms.[25]
Megaphone a ketone derived from the root of Aniba megaphylla.[26]
Mimimycin an anthracycline antibiotic agent named after the character Mimì in La Bohème.[7]
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
Musettamycin an anthracycline antibiotic agent named after the character Musetta in La Bohème.[7]
Naftazone (C11H9N3O2), a vasoprotective drug. The NAFTA free-trade zone is the area covered by NAFTA.[27]
Nonanal (C9H18O), an aldehyde derived from nonane.
Olympiadane A supramolecular compound based on the topology for the Olympic rings.
Orotic acid (pyrimidinecarboxylic acid), has been referred to as vitamin B13.
Penguinone (3,4,4,5-tetramethylcyclohexa-2,5-dienone), so named because its two-dimensional structure resembles a penguin.[28]
Performic acid a strongly oxidizing acid related to formic acid.
Periodic acid (HIO4), pronounced per-iodic and not periodic (like periodic table). Per denotes that iodine is in the highest possible oxidation state.
Picket Fence Porphyrin 5,10,15,20-tetrakis(alpha,alpha,alpha-2-pivalamidophenyl)porphyrin, used to model heme enzyme active sites.
Prismane an isomer of benzene with the carbon atoms arranged in the shape of a triangular prism.
Psicose (C6H12O6), a rare low-calorie sugar that provides 0.3% as much energy as sucrose.
Putrescine a foul-smelling diamine produced by the putrefaction of dead animal tissue.
R-CMP (R-cytodine monophosphate) a component of RNA, but also the acronym for the Royal Canadian Mounted Police.
Rednose a sugar derived from the degradation of rudolphomycin.[7]
Rhamnetin a flavonol dye derived from buckthorn (rhamnus).[29]
Rhamnose a sugar naturally occurring in buckthorn (rhamnus).
Rudolphomycin an anthracycline antibiotic agent named after the character Rodolfo (Rudolph) in La Bohème.[7][30]
Ru(Tris)BiPy-on-a-stick shorthand form of (trans-1,4-bis[(4-pyridyl)ethenyl]benzene)(2,2'-bipyridine)ruthenium(II).[31]
SEX the official abbreviation of sodium ethyl xanthate[32];
Skatole a substance of disagreeable odor that occurs in feces, but also in lower concentrations in flowers, orange blossoms, jasmine.
Spermine, Spermidine, polyamine growth factors involved in cellular metabolism.
Thebacon (C20H23NO4).
Titanic acid the hydrated form of titanium dioxide.
Traumatic acid a substance occurring in plants, with a role in healing damaged tissue.
Unununium (Uuu), the former temporary name of the chemical element number 111, a synthetic transuranium element. This element was named roentgenium (Rg) in November 2004.
Uranate the chemical term for an oxide anion of the element uranium.

References

  • Alex Nickon and Ernest F. Silversmith, "Organic Chemistry, the Name Game: Modern Coined Terms and Their Origins", Pergamon 1987. ISBN 008034481X.
  • W. V. Metanomski, "Unusual Names Assigned to chemical substances", Chem. Int., 1987, 9, 211-215.
  • J. Andraos, "Glossary of Coined Names & Terms Used in Science", York University, 2004.
  • E.C. Alyea, "Metal Complexes of Ditertiary Arsines. Chapter in Transition Metal Complexes of Phosphorus, Arsenic and Antimony Ligands", MacMillan, 1973. Chapter: "Some amusing names of arsine ligands: edas, vdias, dam, ffars etc"
  • Giles, P.M. (1999). "Revised Section F: Natural products and related compounds". Pure Appl. Chem. 71 (4): 587-643. Retrieved on 2007-08-16.
  • Alex Nicko; Ernest F. Silversmith; Organic Chemistry, the Name Game: Modern Coined Terms and Their Origins

See also

External links

Footnotes

  1. Godley, E.W. (1998). Chemical Nomenclature. Kluwer Academic Publishers, 20. ISBN 0751404756. 
  2. Thurlow, Kevin (1998). Chemical Nomenclature. Kluwer Academic Publishers, xii. ISBN 0751404756. 
  3. A more extensive list held at Bristol University
  4. Dennis, Ryan (1997). "Old MacDonald Named a Compound: Branched Enynenynols" (PDF). Journal of Chemical Education 74: 782. Retrieved on 2007-08-16.
  5. Prelog, V., Seiwerth,R. (1941). "". Berichte 74: 1644 and 1769.
  6. Not to be confused with the fictional material Adamantium
  7. 7.0 7.1 7.2 7.3 7.4 7.5 7.6 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):242-58.
  8. 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.
  9. Mikael P. Johansson and Jonas Jusélius (2005). "Arsole Aromaticity Revisited". Lett. Org. Chem. (3): 469–474.
  10. 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: 1514-15. Retrieved on 2007-08-15.
  11. Schleyer, Paul von Rague; Eiji Osawa, Michael G. B. Drew (1968). "Nonacyclo[11.7.1.12,18.03,16.04,13.05,10.06,14.07,11.015,20docosane, a bastard tetramantane]" (PDF). J. Am. Chem. Soc 90 (18): 5034-5036. Retrieved on 2007-08-15.
  12. Kroto, H.W.; Heath, J.R.; O'Brien, S.C.; Curl, R.F.; Smalley, R.E. Nature, 1985, 318(6042), 162
  13. Haymet, A.D.J. J. Am. Chem. Soc. 1986, 108, 319
  14. NORDENSTROM BE (1951). "Effect of cadaverine and lysine on the urinary excretion of piperidine in rabbits". Acta pharmacologica et toxicologica 7 (3): 287-96. PMID 14856760.
  15. CINNAMALDEHYDE: The smell and flavour of cinnamon. Retrieved on 2007-08-16.
  16. D.O. Chester and J.A. Elix, Australian Journal of Chemistry 32 (1979) 2565-2569 doi:10.1071/CH9792565
  17. 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. Retrieved on 2007-08-15.
  18. R A Klein, G P Hazlewood, P Kemp, and R M Dawson, Biochem J. 1979 December 1; 183(3): 691–700
  19. 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.
  20. NIST Standard Reference Database 69, June 2005 Release: NIST Chemistry WebBook - Pentachloronitrobenzene. Retrieved on 2007-08-16.
  21. 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
  22. 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
  23. Hirsutene upside down
  24. Hirsutene upside down
  25. Parent Hydride Names and Substantive Nomenclature, IUPAC, March 2004, pp. 16, <http://www.iupac.org/reports/provisional/abstract04/RB-prs310804/Chap6-3.04.pdf>
  26. SM Kupchan, KL Stevens, EA Rohlfing, BR Sickles, AT Sneden, RW Miller, RF Bryan, J. Org. Chem., 43(4) (1978) 586
  27. 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)]" (in French). Annales d'urologie 6 (3): 209-12. PMID 4562066.
  28. Penguinone - tetramethylcyclohexadienone - Molecular Structure. Retrieved on 2007-08-16.
  29. Uri J, Csoban G, Viragh E., Acta Physiol Hung. 1951;2(2):223-8.
  30. Canadian Patents Database CA 1110562: Anthracycline antibiotic designated RUDOLPHOMYCIN. Retrieved on 2007-08-16.
  31. Toma SH, Uemi M, Nikolaou S, Tomazela DM, Eberlin MN, Toma HE., Inorg Chem. 2004 May 31; 43(11):3521-7
  32. See, for example, N Okibe and DB Johnson, Biotechnology Letters, 2004 24(23), 2011-2016 doi:10.1023/A:1021118915720

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