Parahexyl, also known as synhexyl, is a synthetic homologue of

tetrahydrocannabinol Tetrahydrocannabinol (THC) is a cannabinoid found in cannabis. It is the principal psychoactive constituent of ''Cannabis'' and one of at least 113 total cannabinoids identified on the plant. Although the chemical formula for THC (C21H30O2) de ...

(THC) which was invented in 1941 during attempts to elucidate the structure of Δ⁹-THC, one of the active components of

cannabis ''Cannabis'' () is a genus of flowering plants in the family Cannabaceae that is widely accepted as being indigenous to and originating from the continent of Asia. However, the number of species is disputed, with as many as three species be ...

. Parahexyl is similar in both structure and activity to THC, differing only in the position of one double bond and the lengthening of the chain by one CH₂ group to . Parahexyl produces effects typical of other

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 An agonist is a chemical that activates a Receptor (biochemistry), receptor to produce a biological response. Receptors are Cell (biology), cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an R ...

s in animals. It has a somewhat higher oral

bioavailability In pharmacology, bioavailability is a subcategory of absorption and is the fraction (%) of an administered drug that reaches the systemic circulation. By definition, when a medication is administered intravenously, its bioavailability is 100%. H ...

than THC itself but is otherwise very similar. Presumably, it acts as a CB₁ receptor

in the same way as THC, but as there has been no research published using parahexyl since the discovery of the CB₁ receptor, this has not been definitively confirmed. Parahexyl was occasionally used as an

anxiolytic An anxiolytic (; also antipanic or anti-anxiety agent) is a medication or other intervention that reduces anxiety. This effect is in contrast to anxiogenic agents which increase anxiety. Anxiolytic medications are used for the treatment of anxie ...

in the mid-20th century, the dosage ranging from 5 mg to 90 mg. Parahexyl was made illegal under UN convention in 1971 on the basis of its structural similarity and similar effects profile to THC. Parahexyl was placed into the most restrictive Schedule IReport of the Technical Committee on Schedules I, II, III and I at the United Nations Conference for the adoption of a Protocol on Psychotropic Substances. 15 February 1971. E/CONF.58/L.47 as a compound with no medical use.

Isomerism

At least three isomers of parahexyl have been studied and are known to be active as cannabinoids. Parahexyl itself (i.e. the Δ^6a(10a) isomer) has not had any significant use in scientific research since it was banned internationally in the early 1980s; however, the Δ⁸ and Δ⁹ isomers are both known to be cannabinoid receptor agonists, and Δ⁸-parahexyl has the code number JWH-124, while Δ⁹-parahexyl has been isolated from ''

Cannabis ''Cannabis'' () is a genus of flowering plants in the family Cannabaceae that is widely accepted as being indigenous to and originating from the continent of Asia. However, the number of species is disputed, with as many as three species be ...

'' plant material and assigned the name tetrahydrocannabihexol (THCH). Dibenzopyran and monoterpenoid numbering of tetrahydrocannabinol

Note that 6H-dibenzo ,dyran-1-ol is the same as 6H-benzo hromen-1-ol.

References

{{Cannabinoidergics Benzochromenes Cannabinoids Hydroxyarenes

Isomerism

See also

References