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5F-AMB

5F-AMB
Legal status
Legal status
Identifiers
  • Methyl (2S)-2-{[1-(5-fluoropentyl)-1H-indazol-3-yl]formamido}-3-methylbutanoate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H26FN3O3
Molar mass363.433 g·mol−1
3D model (JSmol)
  • O=C(N[C@H](C(OC)=O)C(C)C)C1=NN(CCCCCF)C2=C1C=CC=C2
  • InChI=1S/C19H26FN3O3/c1-13(2)16(19(25)26-3)21-18(24)17-14-9-5-6-10-15(14)23(22-17)12-8-4-7-11-20/h5-6,9-10,13,16H,4,7-8,11-12H2,1-3H3,(H,21,24)/t16-/m0/s1
  • Key:SAFXSUZMRLTBMM-INIZCTEOSA-N

5F-AMB (also known as 5F-MMB-PINACA and 5F-AMB-PINACA) is an indazole-based synthetic cannabinoid from the indazole-3-carboxamide family,[2] which has been used as an active ingredient in synthetic cannabis products. It was first identified in Japan in early 2014.[3][4] Although only very little pharmacological information about 5F-AMB itself exists,[5] its 4-cyanobutyl analogue (instead of 5-fluoropentyl) has been reported to be a potent agonist for the CB1 receptor (KI = 0.7 nM).[6][7]

  1. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  2. ^ "5-Fluoro-AMB". Cayman Chemical. Retrieved 22 June 2015.
  3. ^ Uchiyama N, Shimokawa Y, Kawamura M, Kikura-Hanajiri R, Hakamatsuka T (August 2014). "Chemical analysis of a benzofuran derivative, 2-(2-ethylaminopropyl)benzofuran (2-EAPB), eight synthetic cannabinoids, five cathinone derivatives, and five other designer drugs newly detected in illegal products". Forensic Toxicology. 32 (2): 266–281. doi:10.1007/s11419-014-0238-5. S2CID 11873421.
  4. ^ Shevyrin V, Melkozerov V, Nevero A, Eltsov O, Shafran Y, Morzherin Y, Lebedev AT (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.
  5. ^ Andersson M, Diao X, Wohlfarth A, Scheidweiler KB, Huestis MA (April 2016). "Metabolic profiling of new synthetic cannabinoids AMB and 5F-AMB by human hepatocyte and liver microsome incubations and high-resolution mass spectrometry". Rapid Communications in Mass Spectrometry. 30 (8): 1067–1078. Bibcode:2016RCMS...30.1067A. doi:10.1002/rcm.7538. PMID 27003044.
  6. ^ WO 2009106980, Buchler IP, Hayes MJ, Hegde SG, Hockerman SL, Jones DE, Kortum SW, Rico JG, Tenbrink RL, Wu LL, "Indazole derivatives", published 3 September 2009, assigned to Pfizer Inc. 
  7. ^ 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.
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