AM-4030

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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	?
ATC code	?
PubChem	10550598
Chemical data
Formula	C27H42O4
Mol. mass	430.618 g/mol
SMILES	eMolecules & PubChem
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?

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]

[edit] References

1. ^ Roger Pertwee. Cannabinoids. Handbook of Experimental Pharmacology Volume 168, p 269. Springer. ISBN 3-540-22565-X
2. ^ 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
3. ^ 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
4. ^ 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

v • d • e Cannabinoids Plant cannabinoids CBD • CBDV • CBN • CBG • CBV • CBL • THC • THC-C4 • THCV Cannabinoid metabolites 11-Hydroxy-THC • 11-nor-9-Carboxy-THC Endogenous cannabinoids Arachidonoyl ethanolamide (Anandamide or AEA) • 2-Arachidonoylglycerol (2-AG) • 2-Arachidonyl glyceryl ether (noladin ether) • Virodhamine • N-arachidonoyl-dopamine (NADA) Synthetic cannabinoid agonists Classical cannabinoids (Dibenzopyrans) A-41988 • Ajulemic acid • AM-087 • AM-411 • AM-855 • AM-905 • AM-906 • AM-919 • AM-938 • AM-4030 • AMG-1 • AMG-3 • AMG-36 • AMG-41 • Dexanabinol (HU-211) • DMHP • Dronabinol • HU-210 • JWH-051 • JWH-133 • JWH-139 • L-759,633 • L-759,656 • Levonantradol • Nabilone • Nabitan • O-806 • O-823 • O-1057 • O-1125 • O-1238 • O-2545 • O-2694 • Parahexyl • THC-O-acetate • THC-O-phosphate Nonclassical cannabinoids CP 47,497 • CP 55,244 • CP 55,940 • HU-308 • 2-Isopropyl-5-methyl-1-(2,6-dihydroxy-4-nonylphenyl)cyclohex-1-ene Aminoalkylindoles AM-630 • AM-1241 • JWH-015 • JWH-018 • JWH-073 • JWH-081 • JWH-200 • L-768,242 • Pravadoline • WIN 55,212-2 Aminoalkylpyrroles JWH-030 • JWH-147 • JWH-307 Eicosanoids AM-883 • Arachidonyl-2'-chloroethylamide • Arachidonylcyclopropylamide • Methanandamide • O-585 • O-689 • O-1812 • O-1860 • O-1861 Others BAY 38-7271 • BAY 59-3074 • JWH-171 • O-2220 Endocannabinoid activity enhancers AM-404 • N-arachidonoyl-serotonin • O-1624 • URB-597 • URB-754 Cannabinoid antagonists and inverse agonists AM-251 • AM-281 • AM-630 • BML-190 • JTE-907 • LY-320,135 • NESS-0327 • O-1184 • O-2050 • O-2654 • Rimonabant • SLV-319 • SR-144,528 • Surinabant • Taranabant • VCHSR