Cannabicyclohexanol (CCH, CP 47,497 dimethyloctyl homologue, (C8)-CP 47,497) is a

cannabinoid Cannabinoids () are several structural classes of compounds found primarily in the ''Cannabis'' plant or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tetrahydrocannabinol (THC) (delta-9-THC), the primary psychoact ...

receptor agonist drug, developed by

Pfizer Pfizer Inc. ( ) is an American Multinational corporation, multinational Pharmaceutical industry, pharmaceutical and biotechnology corporation headquartered at The Spiral (New York City), The Spiral in Manhattan, New York City. Founded in 184 ...

in 1979. On 19 January 2009, the University of Freiburg in Germany announced that an

analog Analog or analogue may refer to: Computing and electronics * Analog signal, in which information is encoded in a continuous variable ** Analog device, an apparatus that operates on analog signals *** Analog electronics, circuits which use analog ...

CP 47,497 CP 47,497 or (C7)-CP 47,497 is a cannabinoid receptor agonist drug, developed by Pfizer in the 1980s. It has analgesic effects and is used in scientific research. It is a potent CB1 agonist with a ''K''d of 2.1 nM. Homologue On the 19th of ...

was the main active ingredient in the herbal incense product ''

Spice In the culinary arts, a spice is any seed, fruit, root, Bark (botany), bark, or other plant substance in a form primarily used for flavoring or coloring food. Spices are distinguished from herbs, which are the leaves, flowers, or stems of pl ...

'', specifically the 1,1-dimethyloctyl homologue of CP 47,497, which is now known as cannabicyclohexanol. The 1,1-dimethyloctyl homologue of CP 47,497 is in fact several times more potent than the parent compound, which is somewhat unexpected as the 1,1-dimethylheptyl is the most potent substituent in classical cannabinoid compounds such as

HU-210 HU-210 is a synthetic cannabinoid that was first synthesized in 1988 from (1''R'',5''S'')- myrtenol by a group led by Raphael Mechoulam at the Hebrew University. HU-210 is 100 to 800 times more potent than natural THC from cannabis and has an ...

Enantiomers

Cannabicyclohexanol has four

enantiomer In chemistry, an enantiomer (Help:IPA/English, /ɪˈnænti.əmər, ɛ-, -oʊ-/ Help:Pronunciation respelling key, ''ih-NAN-tee-ə-mər''), also known as an optical isomer, antipode, or optical antipode, is one of a pair of molecular entities whi ...

s, which by analogy with other related cannabinoid compounds can be expected to have widely varying affinity for cannabinoid receptors, and consequently will show considerable variation in potency. While the (-)-''cis'' enantiomer (-)-cannabicyclohexanol discovered in the original Pfizer research is expected to be the most potent, all four enantiomers have been isolated from illicit samples of this compound, and the properties of the other three enantiomers have not been studied in detail. Most commonly cannabicyclohexanol is encountered as a diastereomeric mix of the two ''cis'' or two ''trans'' isomers in varying ratios, though more rarely a mixture of all four enantiomers has been seen, as well as reasonably enantiopure samples of the most active isomer. Confusion can arise around the naming of these compounds as they can be viewed either as substituted

phenol Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire. The molecule consists of a phenyl group () ...

s or substituted

cyclohexanol Cyclohexanol is the organic compound with the formula HOCH(CH2)5. The molecule is related to cyclohexane by replacement of one hydrogen atom by a hydroxyl group. This compound exists as a deliquescent colorless solid with a camphor-like odor, whi ...

s, but this results in different numbering of the rings. Consequently, the active isomer can be named either 2- 1S,3R)-3-hydroxycyclohexyl5-(2-methylnonan-2-yl)phenol or (1R,3S)-3- -hydroxy-4-(2-methylnonan-2-yl)phenylyclohexan-1-ol.

Toxicity

(C8)-CP 47,497 has been shown to cause DNA damage and inflammation in directly exposed human cells ''in vitro'', though it is unclear if this has any relevance ''in vivo''.

Legal status

Cannabicyclohexanol is not listed in the schedules set out by the

United Nations The United Nations (UN) is the Earth, global intergovernmental organization established by the signing of the Charter of the United Nations, UN Charter on 26 June 1945 with the stated purpose of maintaining international peace and internationa ...

Single Convention on Narcotic Drugs The Single Convention on Narcotic Drugs, 1961 (Single Convention, 1961 Convention, or C61) is an international treaty that controls activities (cultivation, production, supply, trade, transport) involving specific narcotic drugs and lays down a ...

from 1961 nor their

Convention on Psychotropic Substances The Convention on Psychotropic Substances of 1971 is a United Nations treaty designed to control psychoactive drugs such as amphetamine-type stimulants, barbiturates, benzodiazepines, and psychedelics signed in Vienna, Austria on 21 February ...

from 1971, so the signatory countries to these international drug control treaties are not required by said treaties to control Cannabicyclohexanol.

United States

Cannabicyclohexanol is a

Schedule I controlled substance The Controlled Substances Act (CSA) is the statute establishing federal U.S. drug policy under which the manufacture, importation, possession, use, and distribution of certain substances is regulated. It was passed by the 91st United State ...

in the USA.

Vermont

Effective January 1, 2016, cannabicyclohexanol is a regulated drug in Vermont designated as a "Hallucinogenic Drug."

References