AM-2232

{{Short description|Cannabinoid receptor agonist}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 451605653

| IUPAC_name = 5-(3-(1-Naphthoyl)-1H-indol-1-yl)pentanenitrile

| image = AM-2232_structure.png

| image_class = skin-invert-image

| width = 150

| tradename =

| pregnancy_AU =

| pregnancy_US =

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| legal_AU =

| legal_CA = Schedule II

| legal_DE = Anlage II

| legal_UK = Class B

| legal_US = Schedule I

| legal_NZ = Temporary Class

| legal_status =

| routes_of_administration =

| bioavailability =

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| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 335161-19-8

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

| UNII = 40KCH8YIKP

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| PubChem =

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 26633898

| smiles = c1ccc2c(c1)cccc2C(=O)c3cn(c4c3cccc4)CCCCC#N

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C24H20N2O/c25-15-6-1-7-16-26-17-22(20-12-4-5-14-23(20)26)24(27)21-13-8-10-18-9-2-3-11-19(18)21/h2-5,8-14,17H,1,6-7,16H2

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = VWVAIBKHFCUSMD-UHFFFAOYSA-N

| C=24 | H=20 | N=2 | O=1

}}

AM-2232 (1-(4-cyanobutyl)-3-(naphthalen-1-oyl)indole) is a drug that acts as a potent but unselective agonist for the cannabinoid receptors, with a K_i of 0.28 nM at CB₁ and 1.48 nM at CB₂.{{Ref patent2 | country = US | number = 7241799 | status = granted | title = Cannabimimetic indole derivatives | pubdate = 2004-11-05 | gdate = 2007-07-10 | pridate= 2004-11-05 | inventor = Makriyannis A, Deng H | assign1= }}{{cite journal | vauthors = Zagzoog A, Brandt AL, Black T, Kim ED, Burkart R, Patel M, Jin Z, Nikolaeva M, Laprairie RB | title = Assessment of select synthetic cannabinoid receptor agonist bias and selectivity between the type 1 and type 2 cannabinoid receptor | journal = Scientific Reports | volume = 11 | issue = 1 | pages = 10611 | date = May 2021 | pmid = 34012003 | pmc = 8134483 | doi = 10.1038/s41598-021-90167-w }}

In the United States, all CB₁ receptor agonists of the 3-(1-naphthoyl)indole class such as AM-2232 are Schedule I Controlled Substances.{{UnitedStatesCode2|21|812|Schedules of controlled substances}}