AM-4030

AM-4030
Identifiers
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
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC27H42O4
Molar mass430.629 g·mol−1
3D model (JSmol)
SMILES
  • OCC=CC3(C)C1CCC(CO)CC1c2c(O3)cc(cc2O)C(C)(C)CCCCCC
InChI
  • InChI=1S/C27H42O4/c1-5-6-7-8-12-26(2,3)20-16-23(30)25-21-15-19(18-29)10-11-22(21)27(4,13-9-14-28)31-24(25)17-20/h9,13,16-17,19,21-22,28-30H,5-8,10-12,14-15,18H2,1-4H3/b13-9+/t19-,21-,22-,27+/m1/s1 checkY
  • Key:SYKOWCSKDYZBIL-BKTWVJDESA-N checkY
  (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

References

  1. ↑ Pertwee R. "Cannabinoids". Handbook of Experimental Pharmacology. Vol. 168. Springer. p. 269. ISBN 3-540-22565-X.
  2. ↑ Tius MA, Hill WA, Zou XL, Busch-Petersen J, Kawakami JK, Fernandez-Garcia MC, et al. (1995). "Classical/non-classical cannabinoid hybrids; stereochemical requirements for the southern hydroxyalkyl chain". Life Sciences. 56 (23–24): 2007–12. doi:10.1016/0024-3205(95)00182-6. PMID 7776825.
  3. ↑ Drake DJ, Jensen RS, Busch-Petersen J, Kawakami JK, Concepcion Fernandez-Garcia M, Fan P, et al. (September 1998). "Classical/nonclassical hybrid cannabinoids: southern aliphatic chain-functionalized C-6beta methyl, ethyl, and propyl analogues". Journal of Medicinal Chemistry. 41 (19): 3596–608. doi:10.1021/jm960677q. PMID 9733485.
  4. ↑ Thakur GA, Palmer SL, Harrington PE, Stergiades IA, Tius MA, Makriyannis A (December 2002). "Enantiomeric resolution of a novel chiral cannabinoid receptor ligand". Journal of Biochemical and Biophysical Methods. 54 (1–3): 415–22. doi:10.1016/s0165-022x(02)00144-6. PMID 12543516.
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