AM-906

AM-906
Identifiers
	IUPAC name (6aR,9R,10aR)-3-[(Z)-hept-1-enyl]-9-(hydroxymethyl)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-1-ol;
CAS Number	180989-26-8 ;
PubChem CID	10089808;
ChemSpider	8174103 ;
UNII	EW1UQ3B1Y8;
ChEMBL	ChEMBL127848 ;
CompTox Dashboard (EPA)	DTXSID701027470 ;
Chemical and physical data
Formula	C23H34O3
Molar mass	358.522 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCC/C=C\C1=CC2=C(C3CC(CCC3C(O2)(C)C)CO)C(=C1)O;
	InChI InChI=1S/C23H34O3/c1-4-5-6-7-8-9-16-13-20(25)22-18-12-17(15-24)10-11-19(18)23(2,3)26-21(22)14-16/h8-9,13-14,17-19,24-25H,4-7,10-12,15H2,1-3H3/b9-8-/t17-,18-,19-/m1/s1 ; Key:NJIKRWBGUIYKJM-FORFBYLSSA-N ;
	(verify)

AM-906 (part of the AM cannabinoid series) is an analgesic drug which is a cannabinoid agonist. It is conformationally restricted by virtue of the double bond on its side chain, leading an increased affinity for and selectivity between CB₁ and CB₂ receptors.^[1] It is a potent and selective agonist for the CB₁ cannabinoid receptor, with a K_i of 0.8 nM at CB₁ and 9.5 nM at CB₂, a selectivity of almost 12x.^[2]

The corresponding E or trans isomer is AM-905.

References

^ Busch-Petersen J, Hill WA, Fan P, Khanolkar A, Xie XQ, Tius MA, Makriyannis A (September 1996). "Unsaturated side chain beta-11-hydroxyhexahydrocannabinol analogs". Journal of Medicinal Chemistry. 39 (19): 3790–6. doi:10.1021/jm950934b. PMID 8809166.
^ Papahatjis DP, Kourouli T, Abadji V, Goutopoulos A, Makriyannis A (March 1998). "Pharmacophoric requirements for cannabinoid side chains: multiple bond and C1'-substituted delta 8-tetrahydrocannabinols". Journal of Medicinal Chemistry. 41 (7): 1195–200. doi:10.1021/jm970277i. PMC 2291680. PMID 9544219.

[Busch-PetersenHill1996-1] Busch-Petersen J, Hill WA, Fan P, Khanolkar A, Xie XQ, Tius MA, Makriyannis A (September 1996). "Unsaturated side chain beta-11-hydroxyhexahydrocannabinol analogs". Journal of Medicinal Chemistry. 39 (19): 3790–6. doi:10.1021/jm950934b. PMID 8809166.

[2] Papahatjis DP, Kourouli T, Abadji V, Goutopoulos A, Makriyannis A (March 1998). "Pharmacophoric requirements for cannabinoid side chains: multiple bond and C1'-substituted delta 8-tetrahydrocannabinols". Journal of Medicinal Chemistry. 41 (7): 1195–200. doi:10.1021/jm970277i. PMC 2291680. PMID 9544219.

[1]

[2]

See also

References