MMB-2201

{{Short description|Chemical compound}}

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{{Drugbox

| IUPAC_name = (S)-Methyl 2-(1-(5-fluoropentyl)-1H-indole-3-carboxamido)-3-methylbutanoate

| image = 5F-AMB-PICA.svg

| image_class = skin-invert-image

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| legal_CA = Schedule II

| legal_DE = Anlage II

| legal_UK = Class B

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| CAS_number_Ref =

| CAS_number = 1616253-26-9

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| PubChem = 119058037

| ChemSpiderID = 30922499

| SMILES = CC(C)[C@@H](C(=O)OC)NC(=O)c1cn(c2c1cccc2)CCCCCF

| StdInChI = 1S/C20H27FN2O3/c1-14(2)18(20(25)26-3)22-19(24)16-13-23(12-8-4-7-11-21)17-10-6-5-9-15(16)17/h5-6,9-10,13-14,18H,4,7-8,11-12H2,1-3H3,(H,22,24)/t18-/m0/s1

| StdInChIKey = JFXASAFVUQVGEW-SFHVURJKSA-N

| UNII = 744M0WHE80

| C=20 | H=27 | F=1 | N=2 | O=3

}}

MMB-2201 (also known as MMB-5F-PICA,{{cite journal | vauthors = Pulver B, Fischmann S, Gallegos A, Christie R | title = EMCDDA framework and practical guidance for naming synthetic cannabinoids | journal = Drug Testing and Analysis | volume = 15 | issue = 3 | pages = 255–276 | date = March 2023 | pmid = 36346325 | doi = 10.1002/dta.3403 }} 5F-MMB-PICA, 5F-AMB-PICA, and I-AMB) is a potent indole-3-carboxamide based synthetic cannabinoid,{{cite journal | vauthors = Banister SD, Longworth M, Kevin R, Sachdev S, Santiago M, Stuart J, Mack JB, Glass M, McGregor IS, Connor M, Kassiou M | title = Pharmacology of Valinate and tert-Leucinate Synthetic Cannabinoids 5F-AMBICA, 5F-AMB, 5F-ADB, AMB-FUBINACA, MDMB-FUBINACA, MDMB-CHMICA, and Their Analogues | journal = ACS Chemical Neuroscience | volume = 7 | issue = 9 | pages = 1241–1254 | date = September 2016 | pmid = 27421060 | doi = 10.1021/acschemneuro.6b00137 }} which has been sold as a designer drug and as an active ingredient in synthetic cannabis blends.{{cite web | url=https://www.caymanchem.com/app/template/Product.vm/catalog/15971 | title=MMB-2201 | publisher=Cayman Chemical | access-date=16 July 2015}} It was first reported in Russia and Belarus in January 2014, but has since been sold in a number of other countries. In the United States, MMB-2201 was identified in Drug Enforcement Administration drug seizures for the first time in 2018.{{Cite journal | journal = Clinical Pediatric Emergency Medicine | volume = 20 | issue = 1 | date = 2019 | pages = 17–24 | title = Adolescents and Drug Abuse: 21st Century Synthetic Substances | vauthors = Yin S | doi = 10.1016/j.cpem.2019.03.003 | s2cid = 88290992 }}

MMB-2201 is the indole core analogue of 5F-AMB. Synthetic cannabinoid compounds with an indole-3-carboxamide or indazole-3-carboxamide core bearing a N-1-methoxycarbonyl group with attached isopropyl or tert-butyl substituent, have proved to be much more dangerous than older synthetic cannabinoid compounds previously reported, and have been linked to many deaths in Russia, Japan, Europe and the United States.{{cite journal | url=https://www.researchgate.net/publication/263853259 | title=New Synthetic Cannabinoid – Methyl 2-{[1-(5-Fluoro-Pentyl)-3-Methyl-1H -Indol-3-Ylcarbonyl]-Amino}Butyrate – as a Designer Drug | vauthors = Shevyrin VA, Morzherin YY, Melkozerov VP, Nevero AS | journal=Chemistry of Heterocyclic Compounds | date=July 2014 | volume=50 | issue=4 | pages=583–586 | doi=10.1007/s10593-014-1511-6| s2cid=97489753 }}{{cite journal | vauthors = Shevyrin V, Melkozerov V, Nevero A, Eltsov O, Shafran Y, Morzherin Y, Lebedev AT | title = Identification and analytical characteristics of synthetic cannabinoids with an indazole-3-carboxamide structure bearing a N-1-methoxycarbonylalkyl group | journal = Analytical and Bioanalytical Chemistry | volume = 407 | issue = 21 | pages = 6301–6315 | date = August 2015 | pmid = 25893797 | doi = 10.1007/s00216-015-8612-7 | s2cid = 31838655 }}