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" aliphatichydroxyl 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]
^Pertwee R. Cannabinoids. Handbook of Experimental Pharmacology. Vol. 168. Springer. p. 269. ISBN3-540-22565-X.
^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.
^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.
^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.
January 01, 1970
4030, analgesic, drug, which, cannabinoid, receptor, agonist, derivative, which, been, substituted, with, hydroxyprop, enyl, group, this, adds, southern, aliphatic, hydroxyl, group, molecule, seen, series, nonclassical, cannabinoid, drugs, represents, hybrid, . 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 6b 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 AM 4030IdentifiersIUPAC 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 olCAS Number587023 54 9 YPubChem CID10550598ChemSpider8725989 YUNIICGYGFRRXKKChemical and physical dataFormulaC 27H 42O 4Molar mass430 629 g mol 13D model JSmol Interactive imageSMILES OCC CC3 C C1CCC CO CC1c2c O3 cc cc2O C C C CCCCCCInChI 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 YKey SYKOWCSKDYZBIL BKTWVJDESA N Y verify See also editAM 919 AM 938References edit Pertwee R Cannabinoids Handbook of Experimental Pharmacology Vol 168 Springer p 269 ISBN 3 540 22565 X 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 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 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 Retrieved from https en wikipedia org w index php title AM 4030 amp oldid 1199040098, wikipedia, wiki, book, books, library,
