Tetrahydrocannabiphorol (THCP) is a potent

phytocannabinoid Cannabinoids () are several structural classes of compounds found in the cannabis plant primarily and most animal organisms (although insects lack such receptors) or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tet ...

, a CB₁ and CB₂

agonist An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the ago ...

which was known as a synthetic homologue of

THC Tetrahydrocannabinol (THC) 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) describes multiple isomers, the term ''THC'' ...

, but for the first time in 2019 was isolated as a

natural product A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical sy ...

in trace amounts from ''

Cannabis sativa ''Cannabis sativa'' is an annual herbaceous flowering plant indigenous to Eastern Asia, but now of cosmopolitan distribution due to widespread cultivation. It has been cultivated throughout recorded history, used as a source of industrial fiber ...

''. It is structurally similar to Δ⁹-

, the main active component of cannabis, but with the

pentyl Pentyl is a five-carbon alkyl group or substituent with chemical formula -C5H11. It is the substituent form of the alkane pentane. In older literature, the common non-systematic name amyl was often used for the pentyl group. Conversely, the na ...

side chain extended to

heptyl In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl is derived from a cycloalk ...

. Since it has a longer side chain, its

cannabinoid Cannabinoids () are several structural classes of compounds found in the cannabis plant primarily and most animal organisms (although insects lack such receptors) or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tet ...

effects are "far higher than Δ⁹-THC itself." Tetrahydrocannabiphorol has a reported binding affinity approximately 33 times that of Delta-9-THC.

Isomers

Delta-3-THCP

] The Δ³/Δ^6a(10a) isomer Δ³-THCP was synthesised in 1941, and was found to have around the same potency as Delta-3-Tetrahydrocannabinol, Δ³-THC, unlike the hexyl homologue

parahexyl Parahexyl (Synhexyl, n-hexyl-Δ3-THC, (C6)-Δ6a(10a)-THC) is a synthetic homologue of THC which was invented in 1941 during attempts to elucidate the structure of Δ9-THC, one of the active components of cannabis. Parahexyl is similar in both s ...

which was significantly stronger.

Delta-8-THCP

The Δ⁸ isomer is also known as a

synthetic cannabinoid Synthetic cannabinoids are a class of designer drug molecules that bind to the same receptors to which cannabinoids ( THC, CBD and many others) in cannabis plants attach. These novel psychoactive substances should not be confused with synth ...

under the code name JWH-091, It's unconfirmed whether or not Delta-8-THCP is found naturally in cannabis plants, but likely is due to Delta-8-THC itself being a degraded form of Delta-9-THC. JWH-091 has approximately double the binding affinity at the CB1 receptor (22nM ± 3.9nM) in comparison to Delta-9-THC (40.7nM ± 1.7nM) or Delta-8-THC (44nM ± 12nM). but appears significantly lower in vitro than the binding activity of Delta-9-THCP (Ki = 1.2 nM CB1)

References

CB1 receptor agonists Phytocannabinoids Benzochromenes {{cannabinoid-stub

Isomers

Delta-3-THCP

Delta-8-THCP

See also

References