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CB1 receptor agonists
Tetrahydrocannabiphorol
Другие языки:

    Tetrahydrocannabiphorol

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    See also: CBDP
    Not to be confused with THPC.
    Tetrahydrocannabiphorol
    THCP 2D skeletal.svg
    THCP 3D BS.png
    Clinical data
    Other names (-)-Trans-Δ9-tetrahydrocannabiphorol
    Δ9-THCP
    (C7)-Δ9-THC
    THC-Heptyl
    Identifiers
    • (6aR,10aR)-3-heptyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
    CAS Number
    PubChem CID
    ChemSpider
    CompTox Dashboard (EPA)
    Chemical and physical data
    Formula C23H34O2
    Molar mass 342.523 g·mol−1
    3D model (JSmol)
    • CCCCCCCc3cc2OC(C)(C)[C@@H]1CCC(C)=C[C@H]1c2c(O)c3
    • InChI=1S/C23H34O2/c1-5-6-7-8-9-10-17-14-20(24)22-18-13-16(2)11-12-19(18)23(3,4)25-21(22)15-17/h13-15,18-19,24H,5-12H2,1-4H3/t18-,19-/m1/s1
    • Key:OJTMRZHYTZMJKX-RTBURBONSA-N

    Tetrahydrocannabiphorol (THCP) is a potent phytocannabinoid, a CB1 and CB2 agonist which was known as a synthetic homologue of THC, but for the first time in 2019 was isolated as a natural product in trace amounts from Cannabis sativa. It 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 approximately 33 times that of Delta-9-THC.

    Isomers

    Delta-3-THCP

    Δ3-THCP [1]

    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

    JWH-091 (Δ8-THCP) [2], CAS# 51768-60-6

    The Δ8 isomer is also known as a synthetic cannabinoid 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)

    See also


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