AM-4030
 |
|
| Systematic (IUPAC) name | |
|---|---|
|
(6S,6aR,9R,10aR)-9-(hydroxymethyl)-6-[(E)-3-hydroxyprop-1-enyl]-6-methyl-3-(2-methyloctan-2-yl)-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-1-ol
|
|
| Identifiers | |
| CAS Number | 587023-54-9  |
| PubChem | CID 10550598 |
| ChemSpider | 8725989 |
| Chemical data | |
| Formula | C27H42O4 |
| Molar mass | 430.618 g/mol |
|
|
|
|
| (verify) | |
AM-4030 is an analgesic drug which is a cannabinoid receptor agonist. It is a derivative of HU-210 which has been substituted with a 6β-((E)-3-hydroxyprop-1-enyl) group. This adds a "southern" aliphatic hydroxyl group to the molecule as seen in the CP-series of nonclassical cannabinoid drugs, and so AM-4030 represents a hybrid structure between the classical and nonclassical cannabinoid families,[1] with the 6-hydroxyalkyl chain rigidified with a double bond with defined stereochemistry. This gives AM-4030 a greater degree of selectivity, so while it is still a potent agonist at both CB1 and CB2, it is reasonably selective for CB1, with a Ki of 0.7nM at CB1 and 8.6nM at CB2, a selectivity of around 12x.[2][3] Resolution of the enantiomers of AM-4030 yields an even more potent compound, although with less selectivity, with the (-) enantiomer AM-4030a having a Ki of 0.6nM at CB1 and 1.1nM at CB2.[4]
See also[edit]
References[edit]
- ^ Roger Pertwee. Cannabinoids. Handbook of Experimental Pharmacology Volume 168, p 269. Springer. ISBN 3-540-22565-X
- ^ Tius MA, Hill WA, Zou XL, Busch-Petersen J, Kawakami JK, Fernandez-Garcia MC, Drake DJ, Abadji V, Makriyannis A. Classical/non-classical cannabinoid hybrids; stereochemical requirements for the southern hydroxyalkyl chain. Life Sciences. 1995;56(23-24):2007-12. PMID 7776825
- ^ Drake DJ, Jensen RS, Busch-Petersen J, Kawakami JK, Concepcion Fernandez-Garcia M, Fan P, Makriyannis A, Tius MA. Classical/nonclassical hybrid cannabinoids: southern aliphatic chain-functionalized C-6beta methyl, ethyl, and propyl analogues. Journal of Medicinal Chemistry. 1998 Sep 10;41(19):3596-608. PMID 9733485
- ^ Thakur GA, Palmer SL, Harrington PE, Stergiades IA, Tius MA, Makriyannis A. Enantiomeric resolution of a novel chiral cannabinoid receptor ligand. Journal of Biochemical and Biophysical Methods. 2002 Dec 31;54(1-3):415-22. PMID 12543516
