Tetrahydrocannabiphorol

Tetrahydrocannabiphorol
Identifiers
	IUPAC name (6aR,10aR)-3-heptyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol;
CAS Number	54763-99-4;
PubChem CID	6453074;
ChemSpider	4955468;
CompTox Dashboard (EPA)	DTXSID70203228 ;
Chemical and physical data
Formula	C23H34O2
Molar mass	342.523 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCCCc3cc2OC(C)(C)[C@@H]1CCC(C)=C[C@H]1c2c(O)c3;
	InChI 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;

(-)-Trans-Δ⁹-tetrahydrocannabiphorol (Δ⁹-THCP, (C7)-Δ⁹-THC), is a potent phytocannabinoid, a CB₁ and CB₂ agonist which was known as a synthetic homologue of THC,[1] 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." Effects in mice are "hypomotility, analgesia, catalepsy and decreased rectal temperature", similar to those of THC. The corresponding heptyl homologue of cannabidiol was also identified in the same study, and named cannabidiphorol (CBDP).[2]

Cannabidiphorol

The Δ⁸ isomer is also known as a synthetic cannabinoid under the code name JWH-091,[3][4] but it is not known whether it is produced naturally by cannabis plants.

JWH-091 (Δ⁸-THCP)

References

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): 187–97. doi:10.3109/00498258509045349. PMID 2992174.
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. doi:10.1038/s41598-019-56785-1. PMC 6937300. PMID 31889124.
Martin BR, Jefferson R, Winckler R, Wiley JL, Huffman JW, Crocker PJ, Saha B, Razdan RK (September 1999). "Manipulation of the tetrahydrocannabinol side chain delineates agonists, partial agonists, and antagonists". The Journal of Pharmacology and Experimental Therapeutics. 290 (3): 1065–79. PMID 10454479.
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.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[pmid2992174-1] 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): 187–97. doi:10.3109/00498258509045349. PMID 2992174.

[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. doi:10.1038/s41598-019-56785-1. PMC 6937300. PMID 31889124.

[pmid10454479-3] Martin BR, Jefferson R, Winckler R, Wiley JL, Huffman JW, Crocker PJ, Saha B, Razdan RK (September 1999). "Manipulation of the tetrahydrocannabinol side chain delineates agonists, partial agonists, and antagonists". The Journal of Pharmacology and Experimental Therapeutics. 290 (3): 1065–79. PMID 10454479.

[pmid27398024-4] 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.

Tetrahydrocannabiphorol

See also

References