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Molecules with Silly or Unusual NamesBelieve it or not, some chemists do have a sense of humour, and this page is a testament tothat. Here we'll show you some
real
molecules that have unusual, ridiculous or downright sillynames. If you know of any other potential candidates for this page,please let me know. Peoplefrom all over the world have sent me so many contributions to this page, that I've now had tosplit it into three smaller pages. The 3D structure files of many of these molecules can be obtained by clicking on the images.Information on what you need to view these structure files can be foundhere.
Stop Press
: Due to the popularity of this site, I've now written it up as a book, entitled'
Molecules with Silly or Unusual Names
', by Paul May, to be published by World Scientific Press,Summer/Autumn 2008. It should be available at all good bookstores. It will include all yourfavourite molecules from this website, plus some extra information about them. More detailsshortly...
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 pureform, it is occasionally seen as a sidegroup in the form of organic
arsolyls
. Formore information, see the paper with probably the best title of any scientificpaper I've ever come across: "Studies on the Chemistry of the Arsoles", G. Markland H. Hauptmann,
J. Organomet. Chem
.,
248
(1983) 269. Contrary to popularbelief, new research (see reference below) shows that arsoles are onlymoderately aromatic... Incidentally US patent number US 3 412 119 by the DowChemical Company is entitled 'Substituted Stannoles, Phospholes, Arsoles, andStiboles' - I didn't know there was a substitute for an arsole...Furthermore, the structure where arsole is fused to a benzene ring is called'benzarsole', and apparently when it's fused to 6 benzenes it would be called'sexibenzarsole' (although that molecule hasn't been synthesised yet). Anotherwell known poisonous arsenic molecule is the simple hydride, called 'arsine',with formula AsH
3
.And on a related theme, I've been told of an Aryl Selenide compound with thesuperb shorthand of ArSe, which is both toxic and smelly. The paper it comesfrom in J. Am. Chem. Soc.was published by authors from, of course, theUniversity of Aarhus!Also, the related moleculephosphole (which just replaces As with P) is quite
amusing if you are a French speaker, since it's pronounced the same as 'faussefolle'.
Fausse
means 'fake' or 'false', and
folle
means both a 'crazy woman' and a'drag-queen' or 'ladyboy'.
Adamantane
This molecule always brings a smile to the lips of undergrads when they first hearits name, especially in the UK. For those not in the know,
Adam Ant
was an Englishpop star in the early 1980's famous for silly songs and strange make-up.
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 thefield 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 Nobelprize for Chemistry in 1996.It is named after the architect Buckminster Fuller whodesigned the geodesic dome exhibited at Expo '67 in Montreal, from which Sir HarryKroto got the idea how 60 Carbon atoms could be arranged in a perfectlysymmetrical fashion. Because the name of the molecule is a bit of a mouthful, it isoften referred to just as a
. It's also known as 'Footballene' by someresearchers. In fact, there is now a whole'fullerene zoo', with oddly coined names,
including:
Buckybabies
(C
32
, C
44
, C
50
, C
58
),
Rugby Ball
(C
70
),
Giant Fullerenes
(C
240
,C
540
, C
960
),
Russian Egg
or
Bucky Onions
(balls within balls),
Fuzzyball
(C
60
H
60
),
(C
60
(OsO
4
)(4-t-Butylpyridine)
2
),
Platinum-Burr Ball
({[(C
2
H
5
)
3
P]
2
Pt}
6
C
60
) 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 severingtwo adjacent bonds in C
60
, entitled "There Is a Hole in My Bucky" [
J. Am. Chem. Soc
.,
117
(1995) 7003]. Thanks toA. Haymet for the info regarding footballene, and to Charles Turnerfor the
names of the other fullerenes which came from:
'Fullerenes'
, by Robert F. Curl andRichard 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. Itgets its name from being both a constituent of
Aniba Megaphylla
roots and a ketone.[S.M. Kupchan
et al
, '
J.Org.Chem.
',
43
(1987) 586].
Munchnones
No, these aren't the favourite compound of the
Munchkins
from
TheWizard of Oz
, but are in fact a type of mesoionic compound.These are ring
structures in which the positive and negative charge are delocalised, andwhich 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 ridiculousname I thought I'd include it. This is actually element number 111, and wascalled by the IUPAC temporary systematic name of unununium before it wasrecently renamed
roentgenium
. This is a pity, because if it formed ring or cagestructures, previously we might have ended up with unununium onions...[See
Pure and Appl. Chem.
51
pyroxmangite
, withwhite pieces of cummingtonite
Cummingtonite
This mineral must have the silliest name of them all! Its officialname is magnesium iron silicate hydroxide, and it has the formula(Mg,Fe)
7
Si
8
O
22
(OH)
2
. It got its name from the locality where it wasfirst found, Cummington, Massachusetts, USA.
visible toward the lower left.
Putrescine, Cadaverine, Spermine and Spermidine
Putrescine originates in putrefying and rotting flesh, andis quite literally, the smell of death. It is one of thebreakdown products of some of the amino-acids found inanimals, including humans. Although the molecule is apoisonous solid, as flesh decays the vapour pressure of the putrescine it contains becomes sufficiently large toallow its disgusting odour to be detected. It is usuallyaccompanied by cadaverine (named after the cadaversthat give rise to it), a poisonous syrupy liquid with anequally disgusting smell. Putrescine and cadaverine alsocontribute towards the smells of some living processes.Since they are both poisonous, the body normallyexcretes them in whatever way is quickest and mostconvenient. For example, the odour of bad breath andurine are 'enriched' by the presence of these molecules,as is the 'fishy' smell of the discharge from the femalemedical condition
bacterial vaginosis
. Putrescine andcadaverine also contribute to the distinctive smell of semen, which also contains the related moleculesspermine and spermidine. Thanks to Bill Longmanfor suggesting spermine and
spermidine, and to Dr Chris Valentinefor the info about
bacterial vaginosis.
Moronic Acid
This is a triterpenoid organic acid that is found in
Pistacia
resin, and istherefore of interest to people studying archaeological relics, shipwrecksand the contents of ancient Egyptian jars. But why it's called moronicacid is still unknown... Derivatives of this are called
moronates
, as in'which moron-ate the contents of this jar?'
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 curiousproperty it has is that it's sufficiently radioactive that a solution, if concentratedenough, will boil spontaneously after a while. (I wonder if a molecule with 2 Cmatoms in would be 'bi-curious'...?)In a similar way, titanium compounds can be 'titanic', so we get the wonderfullynamed titanic chloride, TiCl
4
. It's also interesting to know that in the titaniumindustry, TiCl
4
is known as 'tickle'. Furthermore, curium oxides are called'curates', so the titanium compound would be
Titanic Curate
, and since curiumcan have more than one valency we could end up with
Curious Curates
. But I'msure these are already a well-known phenomenon...In a similar way, some nickel compounds can be referred to as 'nickelous' - sowe get compounds like
Nickelous Sulfate
(a nice guy by all accounts...)
Fukalite
This wonderfully named mineral gets its name from the Fuka mine in the Fukaregion of southern Japan. It is very rare, and is a form of calcium silico-carbonate,with formula Ca
4
Si
2
O
6
(CO
3
)(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 repairthe trauma - hence its name, and its synonym 'wound hormone'. Thanks toDr Neil Edwardsof Sussex University for supplying this one, and toHan 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 oneconstituent of wine. It's also known as pentahydric alcohol. A related sugarmolecule,
arabinose
, also has nothing to do with rabbits, nor with the sizeof a Rabbi's nose (A Rabbi Nose). Thanks to David Brady for supplying this arabitol, and toDarren Sydenham
for arabinose.
2 layers of dickite.
Dickite
Dickite, Al
2
Si
2
O
5
(OH)
4
, is a (kaolin)clay-like mineral which exhibitsmica-like layers with silicate sheetsof 6-membered rings bonded toaluminium oxide/hydroxide layers.Dickite is used in ceramics, as paintfiller, rubber, plastics and glossypaper. It got its name from thegeologist that discovered it aroundthe 1890s, Dr. W. Thomas Dick, of Lanarkshire, Scotland.Structure from the Virtual Museumof Minerals and Molecules
Fucitol
Although this sounds like what an undergraduate chemist might exclaimwhen their synthesis goes wrong, it's actually an alcohol, whose othernames are L-fuc-ol or 1-deoxy-D-galactitol. It gets its wonderful trivialname from the fact that it is derived from the sugar fucose, which comesfrom a seaweed found in the North Atlantic called Bladderwrack whoselatin name is
Fucus vesiculosis
. Interestingly, there are a few articles inthe
Journal of Biochemistry
throughout 1997 concerning a kinase enzymewhich acts on fucose. The creators of these articles were Japanese, andseemed to have missed the fact that fucose kinase should not beabbreviated as'fuc-K '. Similarly, the
E. coli
Erotic Acid
No, this isn't the world's best aphrodisiac. Its correct name is
orotic acid
, but ithas been misspelt so often in the chemical literature that it is also known aserotic acid! Another name for it is vitamin B13. Apparently, if you add anothercarbon to it, it becomes homo-erotic acid... Thanks to Gerard J. Kleywegtof 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)
3
Si
2
Al
2
O
10
(OH)
2
. It is green and vitreous, and is about ashard 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 andMelita Rowleyfor the
Japanese translation.
Bastadin-5
This is just one of a number of
bastadins
,which are molecules isolated from themarine sponge
Ianthella basta
. They possessantibacterial, cytotoxic and anti-inflammatory properties. Thanks to Neil Edwardsfor 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 asource of strychnine as well as the emetic vomicine. Thanks to Bill LongmanandAlan Howard Martinfor info on this
molecule.
Rhamnose
This sounds like the molecule that's created whenyou 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 asa male contraceptive in China, but was never used in the West (and mayhave since been banned in China as well), since its effects werepermanent in about 20% of patients! Its name originated from beingpresent in the flowers of the Indian cotton plant
Gossypium herbaceum L
.Apart from its contraceptive effects, gossypol has properties that mightmake it useful in treating a number of ailments, including cancer, HIV,malaria and some bacterial/viral illnessness. Related to this molecule arethe equally strangely named
gossypetin
and
gossypin
. I always thought'gossypin' was frowned upon in polite labs... Thanks toLionel Hill for suggesting this molecule, and toAnthony
Argyriou and Kristina Turnerfor providing some of the info.
Skatole
This molecule's name comes from 'skatalogical', meaning concerning fecalmaterial. Its proper name is 3-methylindole, but it gets its trivial name fromthe fact that it is a component of feces. Surprisingly, it is also found in coaltar and beetroot (!), and can be obtained synthetically by mixing eggalbumin and KOH. As you might guess, skatole consists of white to brownishscales which are soluble in hot water. Apparently, coriander can be used tocover up bad smells such as these, as testified in the classic paper:"Deodorizing Effect of Coriander on the Offensive Odor of the Porcine LargeIntestine" [Kohara
et al
,
Food Sci. Technol. Res
.
12
(2006) 38.] Thanks to Allen Knutson for suggesting this molecule, and to Samuel Knightfor providing the info.
Arsenolite
This is a naturally occurring mineral, whose correct name is cubic arsenictrioxide (As
2
O
3
). It is also the primary product whenever arsenic ores aresmelted, and is used in industry as a glass decolourising agent. Anotherrelated mineral with a similar silly name is
arsenolamprite
, which is anative form of arsenic. Thanks to Matthew Latto and Nicholas Welhamfor suggesting these
minerals.
Sexithiophene
This is a 'sexi' molecule - which means it has 6 sub-units, inthis case of thiophene rings. Because of its conjugatedsystem of double bonds, this organic molecule conductselectricity quite well. As a result, it is one of a number of similar molecules being studied for possible uses in organicpolymer electronics. Incidentally, the Latin for 5 sub-unitsis
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 totake things too far.
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