5F-AMB

5F-AMB (also known as 5F-MMB-PINACA and 5F-AMB-PINACA) is an indazole-based synthetic cannabinoid from the indazole-3-carboxamide family,[1] which has been used as an active ingredient in synthetic cannabis products. It was first identified in Japan in early 2014.[2][3] Although only very little pharmacological information about 5F-AMB itself exists,[4] its 4-cyanobutyl analogue (instead of 5-fluoropentyl) has been reported to be a potent agonist for the CB1 receptor (KI = 0.7 nM).[5][6]

5F-AMB
Legal status
Legal status
  • CA: Schedule II
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • UK: Class B
  • US: Schedule I
  • UN: Psychotropic Schedule II
  • Illegal in China, Japan, Sweden, Singapore,
Identifiers
IUPAC name
  • Methyl (2S)-2-{[1-(5-fluoropentyl)-1H-indazol-3-yl]formamido}-3-methylbutanoate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H26FN3O3
Molar mass363.433 g·mol−1
3D model (JSmol)
SMILES
  • O=C(N[C@H](C(OC)=O)C(C)C)C1=NN(CCCCCF)C2=C1C=CC=C2
InChI
  • 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

Side effects

5F-AMB intoxication caused one fatality on its own,[7] 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.[8][9]

Legality

In the United States, 5F-AMB is a Schedule I controlled substance.[10]

5F-AMB is an Anlage II controlled substance in Germany as of May 2015.[11]

Sweden's public health agency suggested classifying 5F-AMB as hazardous substance on November 10, 2014.[12]

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.[13]

5F-AMB is controlled by the Fifth Schedule of the Misuse of Drugs Act (MDA) in Singapore as of May 2015.[14]

5F-AMB was also scheduled in Japan on July 25, 2014.[15]

As of October 2015 5F-AMB is a controlled substance in China.[16]

In December of 2019, the UNODC announced scheduling recommendations placing 5F-MMB-PINACA as a Schedule II controlled research chemical.[17]

See also

References
  1. "5-Fluoro-AMB". Cayman Chemical. Retrieved 22 June 2015.
  2. Nahoko Uchiyama; Yoshihiko Shimokawa; Maiko Kawamura; Ruri Kikura-Hanajiri; Takashi Hakamatsuka (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.
  3. 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.
  4. Maria Andersson; Xingxing Diao; Ariane Wohlfarth; Karl B. Scheidweiler; Marilyn A. Huestis (30 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): 1067–107. Bibcode:2016RCMS...30.1067A. doi:10.1002/rcm.7538. PMID 27003044.
  5. Buchler IP et al., INDAZOLE DERIVATIVES. WO 2009/106980
  6. Banister, Samuel D.; Longworth, Mitchell; Kevin, Richard; Sachdev, Shivani; Santiago, Marina; Stuart, Jordyn; Mack, James B. C.; Glass, Michelle; McGregor, Iain S.; Connor, Mark; Kassiou, Michael (27 July 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): 1241–54. doi:10.1021/acschemneuro.6b00137. PMID 27421060.
  7. Kevin G. Shanks; George S. Behonick (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.
  8. C. Hess; S. Stockhausen; G. Kernbach-Wighton; B. Madea (August 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.
  9. Koutaro Hasegawa; Amin Wurita; Kayoko Minakata; Kunio Gonmori; Hideki Nozawa; Itaru Yamagishi; Kanako Watanabe; Osamu Suzuki (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.
  10. "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.
  11. "Gesetz über den Verkehr mit Betäubungsmitteln (Betäubungsmittelgesetz - BtMG) Anlage II (zu § 1 Abs. 1) (verkehrsfähige, aber nicht verschreibungsfähige Betäubungsmittel)" (in German). Retrieved 22 June 2015.
  12. "Cannabinoider föreslås bli klassade som hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. Retrieved 29 June 2015.
  13. "DHH Adds Two New Synthetic Marijuana Compounds to Banned List". Louisiana Department of Health and Hospitals. 3 June 2014. Retrieved 22 July 2015.
  14. "CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. Archived from the original on 15 July 2015. Retrieved 24 July 2015.
  15. "指定薬物一覧" (PDF) (in Japanese). Ministry of Health, Labour and Welfare.
  16. "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  17. "December 2019 – WHO: World Health Organization recommends 12 NPS for scheduling".
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