Cannabidiphorol

{{Short description|Chemical compound}}

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{{Drugbox

| IUPAC_name = 5-heptyl-2-[(1R,6R)-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-1,3-benzenediol

| image = Cannabidiphorol_structure.png

| image_class = skin-invert-image

| image2 = CBDP 3D BS.png

| image_class2 = bg-transparent

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| CAS_number = 55824-13-0

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| PubChem = 49873141

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| ChemSpiderID = 84400576

| UNII_Ref = {{fdacite|changed|FDA}}

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| C=23 | H=34 | O=2

| smiles = CC(=C)[C@@H]1CCC(C)=C[C@H]1c1c(O)cc(CCCCCCC)cc1O

| StdInChI = 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

| StdInChIKey = GGHRHCGOMWNLCE-VQTJNVASSA-N

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Cannabidiphorol, the heptyl-homologue of cannabidiol was identified as a natural phytocannabinoid and named cannabidiphorol (CBDP) in 2019.{{cite journal | vauthors = Citti C, Linciano P, Russo F, Luongo L, Iannotta M, Maione S, Laganà A, Capriotti AL, Forni F, Vandelli MA, Gigli G, Cannazza G | title = A novel phytocannabinoid isolated from Cannabis sativa L. with an in vivo cannabimimetic activity higher than Δ9-tetrahydrocannabinol: Δ9-Tetrahydrocannabiphorol | journal = Scientific Reports | volume = 9 | issue = 1 | pages = 20335 | date = December 2019 | pmid = 31889124 | pmc = 6937300 | doi = 10.1038/s41598-019-56785-1 | bibcode = 2019NatSR...920335C | doi-access = free }} It had previously been reported as a synthetic compound,{{cite patent | url = https://patents.google.com/patent/US20120172339A1 | country = US | number = 2012/172339 | inventor = Makriyannis A, Nikas SP, Alapafuja SO | title = Angiogenic resorcinol derivatives | pubdate = 5 July 2012 | assign = Northeastern University Boston | status = Abandoned | postscript = . }} 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.{{Cite web | vauthors = Heredia M | date = 27 May 2024 |title=What Is CBDP? Everything You Need To Know |url=https://herb.co/learn/what-is-cbdp-everything-you-need-to-know |access-date=2024-09-13 |website=herb.co |language=en}}

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%.{{cite journal | vauthors = Haghdoost M, et al. | title = CBD Versus CBDP: Comparing In Vitro Receptor-Binding Activities | journal = International Journal of Molecular Sciences | volume = 25 | issue = 14 | pages = 7724 | date = July 2024 | pmid = 39062976 | pmc = 11277192 | doi = 10.3390/ijms25147724 | doi-access = free }}

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

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

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

References

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See also