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Cannabidiphorol

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
Cannabidiphorol
Identifiers
  • 5-heptyl-2-[(1R,6R)-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-1,3-benzenediol
CAS Number
PubChemCID
ChemSpider
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC23H34O2
Molar mass342.523 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, theheptyl-homologue ofcannabidiol was identified as a naturalphytocannabinoid and namedcannabidiphorol (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 since gained popularity due to it being synthesized and available on a commercial level.[3]

Pharmacology

[edit]

Pharmacodynamics

[edit]

CBDP shows weak antagonism at bothcannabinoid receptors (CB1 andCB2), similar to cannabidiol (CBD). CBD, however, exhibits stronger antagonism at CB2, reaching a 33% maximum response ofSR144528 versus CBDP's 23%.[4]

Both cannabinoids act as weak agonists at theserotonin5-HT1A receptor, contributing to potential anxiolytic effects.[4]

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

Unexpectedly, CBDP acts as a positiveallosteric modulator (PAM) at theMOR, enhancingmet-enkephalin signaling by 37%, potentially affecting pain perception.[4]

References

[edit]
  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. ^US Abandoned 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. Retrieved2024-09-13.
  4. ^abcdHaghdoost 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

[edit]
Phytocannabinoids
(comparison)
Cannabibutols
Cannabichromenes
Cannabicyclols
Cannabidiols
Cannabielsoins
Cannabigerols
Cannabiphorols
Cannabinols
Cannabitriols
Cannabivarins
Delta-3-tetrahydrocannabinols
Delta-4-tetrahydrocannabinols
Delta-7-tetrahydrocannabinols
Delta-8-tetrahydrocannabinols
Delta-9-tetrahydrocannabinols
Delta-10-Tetrahydrocannabinols
Delta-11-Tetrahydrocannabinols
Miscellaneous cannabinoids
Active metabolites
Endocannabinoids
Synthetic
cannabinoid
receptor
agonists /
neocannabinoids
Classical cannabinoids
(dibenzopyrans)
Non-classical
cannabinoids
Adamantoylindoles
Benzimidazoles
Benzoylindoles
Cyclohexylphenols
Eicosanoids
Indazole-3-
carboxamides
Indole-3-carboxamides
Indole-3-carboxylates
Naphthoylindazoles
Naphthoylindoles
Naphthoylpyrroles
Naphthylmethylindenes
Naphthylmethylindoles
Phenylacetylindoles
Pyrazolecarboxamides
Tetramethylcyclo-
propanoylindazoles
Tetramethylcyclo-
propanoylindoles
Others
AllostericCBRTooltip Cannabinoid receptorligands
Endocannabinoid
enhancers

(inactivation inhibitors)
Anticannabinoids
(antagonists/inverse
agonists/antibodies)
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