Tetrahydrocannabiphorol
Cannabinoid agonist compound
From Wikipedia, the free encyclopedia
Tetrahydrocannabiphorol (THCP) is a potent phytocannabinoid, a CB1 and CB2 receptor agonist which was known as a synthetic homologue of tetrahydrocannabinol (THC),[1] but for the first time in 2019 was isolated as a natural product in trace amounts from Cannabis sativa.[2][3]
Δ9-THCP,
(C7)-Δ9-THC,
THC-Heptyl
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| Pronunciation | /tɛtʃrəhaɪdroʊkənæbɪfoʊrɔːl/ |
| Other names | (-)-Trans-Δ9-tetrahydrocannabiphorol, Δ9-THCP, (C7)-Δ9-THC, THC-Heptyl |
| Drug class | Cannabinoid |
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| Formula | C23H34O2 |
| Molar mass | 342.523 g·mol−1 |
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THCP is structurally similar to Δ9-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 Δ9-THC itself." Tetrahydrocannabiphorol has a reported binding affinity of 1.2 nM at CB1, approximately 33 times that of Δ9-THC (40 nM at CB1), however this does not mean it's 33x stronger per milligram.[4]
THCP was studied by Roger Adams as early as 1942.[5]
Isomers
Delta-3-THCP
The Δ3/Δ6a(10a) isomer Δ3-THCP was synthesised in 1941, and was found to have around the same potency as Δ3-THC, unlike the hexyl homologue parahexyl which was significantly stronger.[6]
Delta-8-THCP
The Δ8 isomer is also known as a synthetic cannabinoid under the code name JWH-091.[7][8] It's unconfirmed whether or not JWH-091 is found naturally in cannabis plants.[9] JWH-091 has approximately double the binding affinity at the CB1 receptor (22 nM ± 3.9 nM) in comparison to Δ9-THC (40.7 nM ± 1.7 nM) or Δ8-THC (44 nM ± 12 nM),[8] but appears significantly lower in vitro than the binding activity of Δ9-THCP (Ki = 1.2 nM)[4]
Natural cannabis occurrence
The Δ9 isomer of THCP occurs naturally in cannabis plants, but in very small amounts. A 2021 study reported the content of Δ9-THCP ranging from 0.0023% to 0.0136% (w/w) (approximately 0.02–0.13 mg/g) without correlation to THC percentage in Δ9-THC-dominant strains of cannabis; that study failed to detect THCP in CBD-dominant strains.[2][10][11]