5F-AMB explained

Iupac Name:Methyl (2S)-2--3-methylbutanoate
Legal Br:F2
Legal Br Comment:[1]
Legal Ca:Schedule II
Legal Uk:Class B
Legal Us:Schedule I
Legal De:Anlage II
Legal Un:P II
Legal Status:Illegal in China, Japan, Sweden, Singapore,
Cas Number:1801552-03-3
Cas Supplemental:(S-isomer)
1715016-74-2 (racemate)
Pubchem:119025812
Chemspiderid:30646783
Unii:DK24ID0BCL
Kegg:C22802
C:19
H:26
F:1
N:3
O:3
Smiles:O=C(N[C@H](C(OC)=O)C(C)C)C1=NN(CCCCCF)C2=C1C=CC=C2
Stdinchi: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
Stdinchikey: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

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

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

Notes and References

  1. Web site: Anvisa . Brazilian Health Regulatory Agency . 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. live . https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 . 2023-08-27 . 2023-08-27 . . pt-BR . 2023-07-25.
  2. Web site: 5-Fluoro-AMB . Cayman Chemical . 22 June 2015.
  3. 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 . Uchiyama N, Shimokawa Y, Kawamura M, Kikura-Hanajiri R, Hakamatsuka T . Forensic Toxicology . August 2014 . 32 . 2 . 266–281 . 10.1007/s11419-014-0238-5. 11873421 .
  4. Shevyrin V, Melkozerov V, Nevero A, Eltsov O, Shafran Y, Morzherin Y, Lebedev AT . 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 . August 2015 . 25893797 . 10.1007/s00216-015-8612-7 . 31838655 .
  5. Andersson M, Diao X, Wohlfarth A, Scheidweiler KB, Huestis MA . 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 . April 2016 . 27003044 . 10.1002/rcm.7538 . 2016RCMS...30.1067A .
  6. Indazole derivatives . Buchler IP, Hayes MJ, Hegde SG, Hockerman SL, Jones DE, Kortum SW, Rico JG, Tenbrink RL, Wu LL . WO . 2009106980 . Pfizer Inc. . 3 September 2009 .
  7. Banister SD, Longworth M, Kevin R, Sachdev S, Santiago M, Stuart J, Mack JB, Glass M, McGregor IS, Connor M, Kassiou M . 6 . 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 . September 2016 . 27421060 . 10.1021/acschemneuro.6b00137 .
  8. Shanks KG, Behonick GS . Death after use of the synthetic cannabinoid 5F-AMB . Forensic Science International . 262 . e21–e24 . May 2016 . 27017174 . 10.1016/j.forsciint.2016.03.004 .
  9. Hess C, Stockhausen S, Kernbach-Wighton G, Madea B . Death due to diabetic ketoacidosis: Induction by the consumption of synthetic cannabinoids? . Forensic Science International . 257 . e6–e11 . December 2015 . 26363623 . 10.1016/j.forsciint.2015.08.012 .
  10. 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 . Hasegawa K, Wurita A, Minakata K, Gonmori K, Nozawa H, Yamagishi I, Watanabe K, Suzuki O . Forensic Toxicology . January 2015 . 33 . 1 . 45–53 . 10.1007/s11419-014-0245-6. 11884184 .
  11. Web site: 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 . . 2017-03-17 . 2019-10-17 . https://web.archive.org/web/20191017101101/https://www.deadiversion.usdoj.gov/fed_regs/rules/2016/fr1221.htm . dead .
  12. Web site: 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) . de . 22 June 2015.
  13. Web site: Cannabinoider föreslås bli klassade som hälsofarlig vara . Cannabinoids are proposed to be classified as dangerous to health. Folkhälsomyndigheten . sv . 29 June 2015.
  14. Web site: DHH Adds Two New Synthetic Marijuana Compounds to Banned List . Louisiana Department of Health and Hospitals . 3 June 2014 . 22 July 2015 . 18 September 2015 . https://web.archive.org/web/20150918231309/http://dhh.louisiana.gov/index.cfm/newsroom/detail/3059 . dead .
  15. Web site: CNB NEWS RELEASE . Central Narcotics Bureau (CNB) . 30 April 2015 . 24 July 2015 . https://web.archive.org/web/20150715045305/http://www.cnb.gov.sg/Libraries/CNB_Newsroom_Files/CNB_NR_-_30_Apr_2015.sflb.ashx . 15 July 2015 . dead .
  16. Web site: 指定薬物一覧 . List of Designated Drugs. Ministry of Health, Labour and Welfare . ja.
  17. Web site: 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. China Food and Drug Administration . 27 September 2015 . zh . 1 October 2015 . https://web.archive.org/web/20151001222554/http://www.sfda.gov.cn/WS01/CL0056/130753.html . 1 October 2015 . dead .
  18. Web site: December 2019 – WHO: World Health Organization recommends 12 NPS for scheduling.

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