AM-4030
| File:AM-4030.png | |
| Identifiers | |
|---|---|
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| PubChem CID | |
| E number | {{#property:P628}} |
| ECHA InfoCard | {{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value). |
| Chemical and physical data | |
| Formula | C27H42O4 |
| Molar mass | 430.618 g/mol |
| 3D model (JSmol) | |
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AM-4030 is an analgesic drug which is a cannabinoid 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 vs 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]
References
- ↑ 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
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