MMB-2201

MMB-2201 (also known as MMB-5F-PICA,^[1] 5F-MMB-PICA, 5F-AMB-PICA, and I-AMB) is a potent indole-3-carboxamide based synthetic cannabinoid,^[2] which has been sold as a designer drug and as an active ingredient in synthetic cannabis blends.^[3] 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.^[4]

MMB-2201

Legal status
Legal status	CA: Schedule II DE: Anlage II (Authorized trade only, not prescriptible) UK: Class B
Identifiers
IUPAC name (S)-Methyl 2-(1-(5-fluoropentyl)-1H-indole-3-carboxamido)-3-methylbutanoate
CAS Number	1616253-26-9
PubChem CID	119058037
ChemSpider	30922499
UNII	744M0WHE80
CompTox Dashboard (EPA)	DTXSID501342492
Chemical and physical data
Formula	C20H27FN2O3
Molar mass	362.445 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C)[C@@H](C(=O)OC)NC(=O)c1cn(c2c1cccc2)CCCCCF
InChI InChI=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 Key:JFXASAFVUQVGEW-SFHVURJKSA-N

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.^[5][6]

Legality

MMB-2201 is illegal in Russia, Belarus and Sweden.^[7]

See also

• 5F-AB-PINACA
• 5F-ADB
• MDMB-CHMICA
• MDMB-CHMINACA
• MDMB-FUBINACA

References

1. Pulver B, Fischmann S, Gallegos A, Christie R (March 2023). "EMCDDA framework and practical guidance for naming synthetic cannabinoids". Drug Testing and Analysis. 15 (3): 255–276. doi:10.1002/dta.3403. PMID 36346325.
2. Banister SD, Longworth M, Kevin R, Sachdev S, Santiago M, Stuart J, et al. (September 2016). "Pharmacology of Valinate and tert-Leucinate Synthetic Cannabinoids 5F-AMBICA, 5F-AMB, 5F-ADB, AMB-FUBINACA, MDMB-FUBINACA, MDMB-CHMICA, and Their Analogues". ACS Chemical Neuroscience. 7 (9): 1241–1254. doi:10.1021/acschemneuro.6b00137. PMID 27421060.
3. "MMB-2201". Cayman Chemical. Retrieved 16 July 2015.
4. Yin S (2019). "Adolescents and Drug Abuse: 21st Century Synthetic Substances". Clinical Pediatric Emergency Medicine. 20 (1): 17–24. doi:10.1016/j.cpem.2019.03.003. S2CID 88290992.
5. Shevyrin VA, Morzherin YY, Melkozerov VP, Nevero AS (July 2014). "New Synthetic Cannabinoid – Methyl 2-{[1-(5-Fluoro-Pentyl)-3-Methyl-1H -Indol-3-Ylcarbonyl]-Amino}Butyrate – as a Designer Drug". Chemistry of Heterocyclic Compounds. 50 (4): 583–586. doi:10.1007/s10593-014-1511-6. S2CID 97489753.
6. Shevyrin V, Melkozerov V, Nevero A, Eltsov O, Shafran Y, Morzherin Y, et al. (August 2015). "Identification and analytical characteristics of synthetic cannabinoids with an indazole-3-carboxamide structure bearing a N-1-methoxycarbonylalkyl group". Analytical and Bioanalytical Chemistry. 407 (21): 6301–6315. doi:10.1007/s00216-015-8612-7. PMID 25893797. S2CID 31838655.
7. "Cannabinoider föreslås bli klassade som hälsofarlig vara" [Cannabinoids are proposed to be classified as a health hazard]. Folkhälsomyndigheten [The Public Health Authority] (in Swedish). Retrieved 29 June 2015.