AM-4030

{{Short description|Chemical compound}}

{{Drugbox

| verifiedrevid = 448104470

| 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

| image = AM-4030 Structure.svg

| width = 240

| tradename =

| legal_status =

| routes_of_administration =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 587023-54-9

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = CGYGFRRXKK

| PubChem = 10550598

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 8725989

| C=27 | H=42 | O=4

| smiles = OCC=CC3(C)C1CCC(CO)CC1c2c(O3)cc(cc2O)C(C)(C)CCCCCC

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = SYKOWCSKDYZBIL-BKTWVJDESA-N

}}

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,{{cite book | first = Roger | last = Pertwee | name-list-style = vanc | title = Cannabinoids | series = Handbook of Experimental Pharmacology | volume = 168 | page = 269 | publisher = Springer | isbn = 3-540-22565-X }} 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 K_i of 0.7nM at CB₁ and 8.6nM at CB₂, a selectivity of around 12x.{{cite journal | vauthors = Tius MA, Hill WA, Zou XL, Busch-Petersen J, Kawakami JK, Fernandez-Garcia MC, Drake DJ, Abadji V, Makriyannis A | display-authors = 6 | title = Classical/non-classical cannabinoid hybrids; stereochemical requirements for the southern hydroxyalkyl chain | journal = Life Sciences | year = 1995 | volume = 56 | issue = 23–24 | pages = 2007–12 | pmid = 7776825 | doi = 10.1016/0024-3205(95)00182-6 }}{{cite journal | vauthors = Drake DJ, Jensen RS, Busch-Petersen J, Kawakami JK, Concepcion Fernandez-Garcia M, Fan P, Makriyannis A, Tius MA | display-authors = 6 | title = Classical/nonclassical hybrid cannabinoids: southern aliphatic chain-functionalized C-6beta methyl, ethyl, and propyl analogues | journal = Journal of Medicinal Chemistry | volume = 41 | issue = 19 | pages = 3596–608 | date = September 1998 | pmid = 9733485 | doi = 10.1021/jm960677q }} Resolution of the enantiomers of AM-4030 yields an even more potent compound, although with less selectivity, with the (−) enantiomer AM-4030a having a K_i of 0.6nM at CB₁ and 1.1nM at CB₂.{{cite journal | vauthors = Thakur GA, Palmer SL, Harrington PE, Stergiades IA, Tius MA, Makriyannis A | title = Enantiomeric resolution of a novel chiral cannabinoid receptor ligand | journal = Journal of Biochemical and Biophysical Methods | volume = 54 | issue = 1–3 | pages = 415–22 | date = December 2002 | pmid = 12543516 | doi = 10.1016/s0165-022x(02)00144-6 }}