Tetrahydrocannabiphorol

Last updated

Tetrahydrocannabiphorol
THCP 2D skeletal.svg
THCP 3D BS.png
Clinical data
Pronunciation/tɛtʃrəhaɪʒroʊkənæbɪfoʊrɔːl/
Other names(-)-Trans-Δ9-tetrahydrocannabiphorol,
Δ9-THCP,
(C7)-Δ9-THC,
THC-Heptyl
Drug class Cannabinoid
Identifiers
  • (6aR,10aR)-3-heptyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
CAS Number
PubChem CID
ChemSpider
UNII
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 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]

Contents

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). [4]

THCP was studied by Roger Adams as early as 1942. [5]

Isomers

Delta-3-THCP

D -THCP D3-THCP structure.png
Δ -THCP

Delta-8-THCP

JWH-091 (D -THCP) , CAS# 51768-60-6 JWH-091.svg
JWH-091 (Δ -THCP) , CAS# 51768-60-6

The Δ8 isomer is also known as a synthetic cannabinoid under the code name JWH-091. [7] [8] It's unconfirmed whether or not Δ8-THCP is found naturally in cannabis plants, but likely is due to Δ8-THC itself being a degraded form of Δ9-THC. [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, but in 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]

See also

References

  1. ↑ Harvey DJ (March 1985). "Identification of hepatic metabolites of n-heptyl-delta-1-tetrahydrocannabinol in the mouse". Xenobiotica; the Fate of Foreign Compounds in Biological Systems. 15 (3): 187–197. doi:10.3109/00498258509045349. PMID   2992174.
  2. 1 2 Bueno J, Greenbaum EA (February 2021). "(-)-trans-Δ9-Tetrahydrocannabiphorol Content of Cannabis sativa Inflorescence from Various Chemotypes". Journal of Natural Products. 84 (2): 531–536. doi:10.1021/acs.jnatprod.0c01034. PMID   33565878. S2CID   231866062.
  3. ↑ Linciano P, Russo F, Citti C, Tolomeo F, Paris R, Fulvio F, et al. (December 2021). "The novel heptyl phorolic acid cannabinoids content in different Cannabis sativa L. accessions". Talanta. 235: 122704. doi:10.1016/j.talanta.2021.122704. hdl: 11380/1250339 . PMID   34517579.
  4. 1 2 Citti C, Linciano P, Russo F, Luongo L, Iannotta M, Maione S, et al. (December 2019). "A novel phytocannabinoid isolated from Cannabis sativa L. with an in vivo cannabimimetic activity higher than Δ9-tetrahydrocannabinol: Δ9-Tetrahydrocannabiphorol". Scientific Reports. 9 (1): 20335. Bibcode:2019NatSR...920335C. doi:10.1038/s41598-019-56785-1. PMC   6937300 . PMID   31889124.
  5. ↑ Adams R, Loewe S, Smith CM, McPhee WD (1942). "Tetrahydrocannabinol Homologs and Analogs with Marihuana Activity. XIII1". Journal of the American Chemical Society. 64 (3): 694–697. doi:10.1021/ja01255a061.
  6. ↑ Adams R, Loewe S, Jelinek C, Wolff H (July 1941). "Tetrahydrocannabinol Homologs with Marihuana Activity. IX". Journal of the American Chemical Society. 63 (7): 1971–1973. doi:10.1021/ja01852a052.
  7. ↑ Martin BR, Jefferson R, Winckler R, Wiley JL, Huffman JW, Crocker PJ, et al. (September 1999). "Manipulation of the tetrahydrocannabinol side chain delineates agonists, partial agonists, and antagonists". The Journal of Pharmacology and Experimental Therapeutics. 290 (3): 1065–1079. PMID   10454479.
  8. 1 2 Bow EW, Rimoldi JM (2016). "The Structure-Function Relationships of Classical Cannabinoids: CB1/CB2 Modulation". Perspectives in Medicinal Chemistry. 8: 17–39. doi:10.4137/PMC.S32171. PMC   4927043 . PMID   27398024.
  9. ↑ Hazekamp A, Fischedick JT, Díez ML, Lubbe A, Ruhaak RL (2010). "Chemistry of Cannabis". Comprehensive Natural Products II. pp. 1033–1084. doi:10.1016/B978-008045382-8.00091-5. ISBN   978-0-08-045382-8.
  10. ↑ Bueno J, Greenbaum EA (2021). "(-)- trans-Δ9-Tetrahydrocannabiphorol Content of Cannabis sativa Inflorescence from Various Chemotypes". Journal of Natural Products. 84 (2): 531–536. doi:10.1021/acs.jnatprod.0c01034. PMID   33565878. S2CID   231866062 . Retrieved 19 Feb 2024.
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