Tetrahydrocannabiphorol (THCP) is a potent phytocannabinoid, a CB<sub>1</sub> and CB<sub>2</sub> receptor agonist which was known as a synthetic homologue of tetrahydrocannabinol (THC), but for the first time in 2019 was isolated as a natural product in trace amounts from Cannabis sativa.
THCP is structurally similar to ÃÂ<sup>9</sup>-THC, the main active component of cannabis, but with the pentyl side chain extended to heptyl. Since it has a longer side chain, its cannabinoid effects are "far higher than ÃÂ<sup>9</sup>-THC itself." Tetrahydrocannabiphorol has a reported binding affinity of 1.2 nM at CB<sub>1</sub>, approximately 33 times that of ÃÂ<sup>9</sup>-THC (40 nM at CB<sub>1</sub>), however this does not mean it's 33x stronger per milligram.
THCP was studied by Roger Adams as early as 1942.
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The ÃÂ<sup>3</sup>/ÃÂ<sup>6a(10a)</sup> isomer ÃÂ<sup>3</sup>-THCP was synthesised in 1941, and was found to have around the same potency as ÃÂ<sup>3</sup>-THC, unlike the hexyl homologue parahexyl which was significantly stronger.
The ÃÂ<sup>8</sup> isomer is also known as a synthetic cannabinoid under the code name JWH-091. It's unconfirmed whether or not JWH-091 is found naturally in cannabis plants. JWH-091 has approximately double the binding affinity at the CB<sub>1</sub> receptor (22 nM ñ 3.9 nM) in comparison to ÃÂ<sup>9</sup>-THC (40.7 nM ñ 1.7 nM) or ÃÂ<sup>8</sup>-THC (44 nM ñ 12 nM), but appears significantly lower in vitro than the binding activity of ÃÂ<sup>9</sup>-THCP (K<sub>i</sub>âÂÂ=âÂÂ1.2 nM)
The ÃÂ<sup>9</sup> isomer of THCP occurs naturally in cannabis plants, but in very small amounts. A 2021 study reported the content of ÃÂ<sup>9</sup>-THCP ranging from 0.0023% to 0.0136% (w/w) (approximately 0.02âÂÂ0.13 mg/g) without correlation to THC percentage in ÃÂ<sup>9</sup>-THC-dominant strains of cannabis; that study failed to detect THCP in CBD-dominant strains.