AM-1241

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 477235775

| IUPAC_name = (2-Iodo-5-nitrophenyl)-[1-[(1-methylpiperidin-2-yl)methyl]indol-3-yl]methanone

| image = AM-1241-2D-skeletal.svg

| tradename =

| pregnancy_AU =

| pregnancy_US =

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| legal_AU =

| legal_CA = Schedule II

| legal_DE = NpSG

| legal_UK = PSA

| legal_US =

| legal_status =

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| IUPHAR_ligand = 3316

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

| CAS_number = 444912-48-5

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

| UNII = DLM851L3RD

| ATC_prefix =

| ATC_suffix =

| PubChem = 10141893

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

| DrugBank =

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

| ChemSpiderID = 8317404

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

| ChEMBL = 408430

| C=22 | H=22 | I=1 | N=3 | O=3

| smiles = Ic2ccc(N(=O)=O)cc2C(=O)c(c4ccccc14)cn1CC3CCCCN3C

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

| StdInChI = 1S/C22H22IN3O3/c1-24-11-5-4-6-16(24)13-25-14-19(17-7-2-3-8-21(17)25)22(27)18-12-15(26(28)29)9-10-20(18)23/h2-3,7-10,12,14,16H,4-6,11,13H2,1H3

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

| StdInChIKey = ZUHIXXCLLBMBDW-UHFFFAOYSA-N

}}

AM-1241 (1-(methylpiperidin-2-ylmethyl)-3-(2-iodo-5-nitrobenzoyl)indole) is a chemical from the aminoalkylindole family that acts as a potent and selective agonist for the cannabinoid receptor CB₂,{{cite journal | vauthors = Yao BB, Mukherjee S, Fan Y, Garrison TR, Daza AV, Grayson GK, Hooker BA, Dart MJ, Sullivan JP, Meyer MD | display-authors = 6 | title = In vitro pharmacological characterization of AM1241: a protean agonist at the cannabinoid CB2 receptor? | journal = British Journal of Pharmacology | volume = 149 | issue = 2 | pages = 145–54 | date = September 2006 | pmid = 16894349 | pmc = 2013801 | doi = 10.1038/sj.bjp.0706838 }}{{cite journal | vauthors = Bingham B, Jones PG, Uveges AJ, Kotnis S, Lu P, Smith VA, Sun SC, Resnick L, Chlenov M, He Y, Strassle BW, Cummons TA, Piesla MJ, Harrison JE, Whiteside GT, Kennedy JD | display-authors = 6 | title = Species-specific in vitro pharmacological effects of the cannabinoid receptor 2 (CB2) selective ligand AM1241 and its resolved enantiomers | journal = British Journal of Pharmacology | volume = 151 | issue = 7 | pages = 1061–70 | date = August 2007 | pmid = 17549048 | pmc = 2042933 | doi = 10.1038/sj.bjp.0707303 }} with a K_i of 3.4 nM at CB₂ and 80 times selectivity over the related CB₁ receptor.{{cite journal | vauthors = Ibrahim MM, Deng H, Zvonok A, Cockayne DA, Kwan J, Mata HP, Vanderah TW, Lai J, Porreca F, Makriyannis A, Malan TP | display-authors = 6 | title = Activation of CB2 cannabinoid receptors by AM1241 inhibits experimental neuropathic pain: pain inhibition by receptors not present in the CNS | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 100 | issue = 18 | pages = 10529–33 | date = September 2003 | pmid = 12917492 | pmc = 193595 | doi = 10.1073/pnas.1834309100 | bibcode = 2003PNAS..10010529I | doi-access = free }}{{cite journal | vauthors = Marriott KS, Huffman JW | title = Recent advances in the development of selective ligands for the cannabinoid CB(2) receptor | journal = Current Topics in Medicinal Chemistry | volume = 8 | issue = 3 | pages = 187–204 | year = 2008 | pmid = 18289088 | doi = 10.2174/156802608783498014 }} It has analgesic effects in animal studies, particularly against "atypical" pain such as hyperalgesia and allodynia.{{cite journal | vauthors = Beltramo M, Bernardini N, Bertorelli R, Campanella M, Nicolussi E, Fredduzzi S, Reggiani A | title = CB2 receptor-mediated antihyperalgesia: possible direct involvement of neural mechanisms | journal = The European Journal of Neuroscience | volume = 23 | issue = 6 | pages = 1530–8 | date = March 2006 | pmid = 16553616 | doi = 10.1111/j.1460-9568.2006.04684.x | s2cid = 19266396 }} This is thought to be mediated through CB₂-mediated peripheral release of endogenous opioid peptides,{{cite journal | vauthors = Ibrahim MM, Porreca F, Lai J, Albrecht PJ, Rice FL, Khodorova A, Davar G, Makriyannis A, Vanderah TW, Mata HP, Malan TP | display-authors = 6 | title = CB2 cannabinoid receptor activation produces antinociception by stimulating peripheral release of endogenous opioids | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 102 | issue = 8 | pages = 3093–8 | date = February 2005 | pmid = 15705714 | pmc = 549497 | doi = 10.1073/pnas.0409888102 | bibcode = 2005PNAS..102.3093I | doi-access = free }} as well as direct activation of the TRPA1 channel.{{cite journal | vauthors = Akopian AN, Ruparel NB, Patwardhan A, Hargreaves KM | title = Cannabinoids desensitize capsaicin and mustard oil responses in sensory neurons via TRPA1 activation | journal = The Journal of Neuroscience | volume = 28 | issue = 5 | pages = 1064–75 | date = January 2008 | pmid = 18234885 | pmc = 6671418 | doi = 10.1523/JNEUROSCI.1565-06.2008 | doi-access = free }} It has also shown efficacy in the treatment of amyotrophic lateral sclerosis in animal models.{{cite journal | vauthors = Kim K, Moore DH, Makriyannis A, Abood ME | title = AM1241, a cannabinoid CB2 receptor selective compound, delays disease progression in a mouse model of amyotrophic lateral sclerosis | journal = European Journal of Pharmacology | volume = 542 | issue = 1–3 | pages = 100–5 | date = August 2006 | pmid = 16781706 | doi = 10.1016/j.ejphar.2006.05.025 | authorlink3 = Alexandros Makriyannis }}{{cite journal | vauthors = Shoemaker JL, Seely KA, Reed RL, Crow JP, Prather PL | title = The CB2 cannabinoid agonist AM-1241 prolongs survival in a transgenic mouse model of amyotrophic lateral sclerosis when initiated at symptom onset | journal = Journal of Neurochemistry | volume = 101 | issue = 1 | pages = 87–98 | date = April 2007 | pmid = 17241118 | pmc = 2819701 | doi = 10.1111/j.1471-4159.2006.04346.x }}