Cannabidiphorol

Last updated

Cannabidiphorol
Cannabidiphorol structure.png
CBDP 3D BS.png
Identifiers
  • 5-heptyl-2-[(1R,6R)-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-1,3-benzenediol
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
Formula C23H34O2
Molar mass 342.523 g·mol−1
3D model (JSmol)
  • CC(=C)[C@@H]1CCC(C)=C[C@H]1c1c(O)cc(CCCCCCC)cc1O
  • InChI=1S/C23H34O2/c1-5-6-7-8-9-10-18-14-21(24)23(22(25)15-18)20-13-17(4)11-12-19(20)16(2)3/h13-15,19-20,24-25H,2,5-12H2,1,3-4H3/t19-,20+/m0/s1
  • Key:GGHRHCGOMWNLCE-VQTJNVASSA-N

Cannabidiphorol, the heptyl-homologue of cannabidiol was identified as a natural phytocannabinoid and named cannabidiphorol (CBDP) in 2019. [1] It had previously been reported as a synthetic compound, [2] but was not identified as a natural product prior to 2019. Recently, CBDP has been gained popularity due to it being synthesized and available on a commercial level. [3]

Contents

Pharmacology

Pharmacodynamics

CBDP shows weak antagonism at both cannabinoid receptors (CB1 and CB2), similar to cannabidiol (CBD). CBD, however, exhibits stronger antagonism at CB2, reaching a 33% maximum response of SR144528 versus CBDP's 23%. [4]

Both cannabinoids act as weak agonists at the serotonin 5-HT1A receptor, contributing to potential anxiolytic effects. [4]

Unlike CBD, CBDP shows no sign of dopamine D2 receptor agonism. [4]

Unexpectedly, CBDP acts as a positive allosteric modulator (PAM) at the MOR, enhancing met-enkephalin signaling by 37%, potentially affecting pain perception. [4]

References

  1. ↑ 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.
  2. ↑ USAbandoned 2012/172339,Makriyannis A, Nikas SP, Alapafuja SO,"Angiogenic resorcinol derivatives",published 5 July 2012, assigned to Northeastern University Boston.
  3. ↑ Heredia M (27 May 2024). "What Is CBDP? Everything You Need To Know". herb.co. Retrieved 2024-09-13.
  4. 1 2 3 4 Haghdoost M, et al. (July 2024). "CBD Versus CBDP: Comparing In Vitro Receptor-Binding Activities". International Journal of Molecular Sciences. 25 (14): 7724. doi: 10.3390/ijms25147724 . PMC   11277192 . PMID   39062976.

See also

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