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AM-4030

AM-4030
AM-4030.png
Identifiers
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC27H42O4
Molar mass430.618 g/mol g·mol−1
3D model (JSmol)
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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. 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. "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.