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5F-AMB

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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]

Side effects

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5F-AMB intoxication caused one fatality on its own,[8] another through ketoacidosis in combination with AB-CHMINACA, AB-FUBINACA, AM-2201, 5F-APINACA, EAM-2201, JWH-018, JWH-122, MAM-2201, STS-135 and THJ-2201 and another fatality in combination with AB-CHMINACA and Diphenidine.[9][10]

Legality

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In the United States, 5F-AMB is a Schedule I controlled substance.[11]

5F-AMB is an Anlage II controlled substance in Germany as of May 2015.[12]

Sweden's public health agency suggested classifying 5F-AMB as hazardous substance on November 10, 2014.[13]

The state of Louisiana banned 5F-AMB through an emergency rule after it was detected in a synthetic cannabinoids product called "Kali Berry 2" on 3 June 2014.[14]

5F-AMB is controlled by the Fifth Schedule of the Misuse of Drugs Act (MDA) in Singapore as of May 2015.[15]

5F-AMB was also scheduled in Japan on July 25, 2014.[16]

As of October 2015 5F-AMB is a controlled substance in China.[17]

In December 2019, the UNODC announced scheduling recommendations placing 5F-MMB-PINACA as a Schedule II controlled research chemical.[18]

See also

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References

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  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.
  8. ^ Shanks KG, Behonick GS (May 2016). "Death after use of the synthetic cannabinoid 5F-AMB". Forensic Science International. 262: e21–e24. doi:10.1016/j.forsciint.2016.03.004. PMID 27017174.
  9. ^ Hess C, Stockhausen S, Kernbach-Wighton G, Madea B (December 2015). "Death due to diabetic ketoacidosis: Induction by the consumption of synthetic cannabinoids?". Forensic Science International. 257: e6–e11. doi:10.1016/j.forsciint.2015.08.012. PMID 26363623.
  10. ^ Hasegawa K, Wurita A, Minakata K, Gonmori K, Nozawa H, Yamagishi I, Watanabe K, Suzuki O (January 2015). "Postmortem distribution of AB-CHMINACA, 5-fluoro-AMB, and diphenidine in body fluids and solid tissues in a fatal poisoning case: usefulness of adipose tissue for detection of the drugs in unchanged forms". Forensic Toxicology. 33 (1): 45–53. doi:10.1007/s11419-014-0245-6. S2CID 11884184.
  11. ^ "Schedules of Controlled Substances: Temporary Placement of Six Synthetic Cannabinoids (5F-ADB, 5F-AMB, 5F-APINACA, ADB-FUBINACA, MDMB-CHMICA and MDMB-FUBINACA) Into Schedule I". Drug Enforcement Administration. Archived from the original on 2019-10-17. Retrieved 2017-03-17.
  12. ^ "Gesetz über den Verkehr mit Betäubungsmitteln (Betäubungsmittelgesetz - BtMG) Anlage II (zu § 1 Abs. 1) (verkehrsfähige, aber nicht verschreibungsfähige Betäubungsmittel)" [German Narcotics Act (Narcotic Drugs Act - BtMG) Annex II (to Section 1 (1)) (narcotics that can be marketed but not prescribed)] (in German). Retrieved 22 June 2015.
  13. ^ "Cannabinoider föreslås bli klassade som hälsofarlig vara" [Cannabinoids are proposed to be classified as dangerous to health] (in Swedish). Folkhälsomyndigheten. Retrieved 29 June 2015.
  14. ^ "DHH Adds Two New Synthetic Marijuana Compounds to Banned List". Louisiana Department of Health and Hospitals. 3 June 2014. Archived from the original on 18 September 2015. Retrieved 22 July 2015.
  15. ^ "CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. Archived from the original on 15 July 2015. Retrieved 24 July 2015.
  16. ^ "指定薬物一覧" [List of Designated Drugs] (PDF) (in Japanese). Ministry of Health, Labour and Welfare.
  17. ^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" [On the issuance of non-pharmaceutical narcotic drugs and psychotropic substances listed in the notice] (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  18. ^ "December 2019 – WHO: World Health Organization recommends 12 NPS for scheduling".
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