Tetrahydrocannabiphorol (THCP) is a potent phytocannabinoid, a CB1 and CB2 receptor agonist which was known as a synthetic homologue of tetrahydrocannabinol (THC), but for the first time in 2019 was isolated as a trace natural product from Cannabis sativa.
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.
THCP was studied by Roger Adams as early as 1942.
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.
Delta-8-THCP
The Δ8 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 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), but appears significantly lower in vitro than the binding activity of Δ9-THCP (Ki = 1.2 nM)
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 biomass) without correlation to THC percentage in Δ9-THC-dominant strains of cannabis; that study failed to detect THCP in CBD-dominant strains. See also Δ8-THC-DMH Nabilone Hexahydrocannabiphorol (HHCP) 1,2-Didehydro-3-oxo-THCO Delta-8-THC Parahexyl Perrottetinene Tetrahydrocannabivarin (THCV) Tetrahydrocannabutol Tetrahydrocannabihexol (THCH) THCP-O-acetate Cannabidiphorol (CBDP)
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