AM-905

AM-905 (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 reasonably selective agonist for the CB₁ cannabinoid receptor, with a K_i of 1.2 nM at CB₁ and 5.3 nM at CB₂.[2]

AM-905

Identifiers
IUPAC name (6aR,9R,10aR)-3-[(E)-hept-1-enyl]-9-(hydroxymethyl)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-1-ol
CAS Number	181139-62-8
PubChem CID	9998522
ChemSpider	8174103
UNII	TJ6JD73J07
ChEMBL	ChEMBL127848
Chemical and physical data
Formula	C23H34O3
Molar mass	358.522 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CCCCC/C=C/c(cc1O)cc(OC(C)(C)C2CC3)c1C2CC3CO
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-OKMMTOMJSA-N
(verify)

See also

• AM-906 - The corresponding Z or cis isomer
• HU-243 - Double bond replaced by geminal methyls for Thorpe–Ingold effect

References

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. PMID 9544219.