AM-905

AM-905

Systematic (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
Identifiers
CAS Number	181139-62-8
PubChem	CID 9998522
ChemSpider	8174103
ChEMBL	CHEMBL127848
Chemical data
Formula	C23H34O3
Molar mass	358.513 g/mol
SMILES CCCCCC=Cc(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
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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 1.2nM at CB₁ and 5.3nM at CB₂.^[2]

See Also

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

References

1. Busch-Petersen, Jakob; Hill, W. Adam; Fan, Pusheng; Khanolkar, Atmaram; Xie, Xuang-Qun; Tius, Marcus A.; Makriyannis, Alexandros (1996). "Unsaturated Side Chain β-11-Hydroxyhexahydrocannabinol Analogs". Journal of Medicinal Chemistry 39 (19): 3790–3796. doi:10.1021/jm950934b. ISSN 0022-2623.
2. Papahatjis DP, Kourouli T, Abadji V, Goutopoulos A, Makriyannis A. Pharmacophoric requirements for cannabinoid side chains: multiple bond and C1'-substituted delta 8-tetrahydrocannabinols. Journal of Medicinal Chemistry. 1998 Mar 26;41(7):1195-200. PMID 9544219