MMB-2201

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

MMB-2201
Legal status
Legal status
Identifiers
IUPAC name
  • (S)-Methyl 2-(1-(5-fluoropentyl)-1H-indole-3-carboxamido)-3-methylbutanoate
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC20H27FN2O3
Molar mass362.445 g·mol−1
3D model (JSmol)
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.[4][5]

Legality

MMB-2201 is illegal in Russia, Belarus and Sweden.[6]

See also

References
  1. Samuel D Banister; et al. (July 2016). "The 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): 1241–54. doi:10.1021/acschemneuro.6b00137. PMID 27421060.
  2. "MMB-2201". Cayman Chemical. Retrieved 16 July 2015.
  3. Shan Yin (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.
  4. V. A. Shevyrin; Yu. Yu. Morzherin; V. P. Melkozerov; A. S. Nevero (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.
  5. Shevyrin V, Melkozerov V, Nevero A, Eltsov O, Shafran Y, Morzherin Y, Lebedev AT (Apr 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): 6301–15. doi:10.1007/s00216-015-8612-7. PMID 25893797. S2CID 31838655.
  6. "Cannabinoider föreslås bli klassade som hälsofarlig vara". Folkhälsomyndigheten. Retrieved 29 June 2015.
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