AM-411

{{Short description|Chemical compound}}

{{Drugbox

| verifiedrevid = 415995491

| IUPAC_name = (6aR,10aR)-3-(1-Adamantyl)-6,6,9-trimethyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol

| image = AM-411 Structure.svg

| image_class = skin-invert-image

| width = 240

| tradename =

| legal_status =

| routes_of_administration =

| metabolism =

| elimination_half-life =

| excretion =

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

| CAS_number = 212835-02-4

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

| UNII = 2K9WS7SUR3

| PubChem = 9799945

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

| ChemSpiderID = 7975710

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 434351

| C=26 | H=34 | O=2

| smiles = C5C6CC4CC5(CC(C6)C4)c(cc1O3)cc(O)c1C2CC(C)=CCC2C3(C)C

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

| StdInChI = 1S/C26H34O2/c1-15-4-5-21-20(6-15)24-22(27)10-19(11-23(24)28-25(21,2)3)26-12-16-7-17(13-26)9-18(8-16)14-26/h4,10-11,16-18,20-21,27H,5-9,12-14H2,1-3H3/t16?,17?,18?,20-,21-,26?/m1/s1

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

| StdInChIKey = RPBMPWGKZFLMFN-OKFSJJLXSA-N

}}

AM-411 (part of the AM cannabinoid series) is an analgesic drug that is a cannabinoid agonist. It is a derivative of Δ8-THC substituted with an adamantyl group at the 3-position, demonstrating that the binding pocket for the alkyl chain at this position can accommodate significant bulk.

AM-411 is a potent and fairly selective CB₁ full agonist with a K_i of 6.80 nM, but is still also a moderately potent CB₂ agonist with a K_i of 52.0 nM.{{cite journal | vauthors = Lu D, Meng Z, Thakur GA, Fan P, Steed J, Tartal CL, Hurst DP, Reggio PH, Deschamps JR, Parrish DA, George C, Järbe TU, Lamb RJ, Makriyannis A | display-authors = 6 | title = Adamantyl cannabinoids: a novel class of cannabinergic ligands | journal = Journal of Medicinal Chemistry | volume = 48 | issue = 14 | pages = 4576–85 | date = July 2005 | pmid = 15999995 | doi = 10.1021/jm058175c }} It produces similar effects to other cannabinoid agonists such as analgesia, sedation, and anxiolysis.{{cite journal | vauthors = Järbe TU, DiPatrizio NV, Lu D, Makriyannis A | title = (−)-Adamantyl-delta8-tetrahydrocannabinol (AM-411), a selective cannabinoid CB1 receptor agonist: effects on open-field behaviors and antagonism by SR-141716 in rats | journal = Behavioural Pharmacology | volume = 15 | issue = 7 | pages = 517–21 | date = November 2004 | pmid = 15472574 | doi = 10.1097/00008877-200411000-00008 | s2cid = 23889056 }}{{cite journal | vauthors = McLaughlin PJ, Lu D, Winston KM, Thakur G, Swezey LA, Makriyannis A, Salamone JD | title = Behavioral effects of the novel cannabinoid full agonist AM 411 | journal = Pharmacology, Biochemistry, and Behavior | volume = 81 | issue = 1 | pages = 78–88 | date = May 2005 | pmid = 15894067 | doi = 10.1016/j.pbb.2005.02.005 | s2cid = 806517 }}