5F-AB-PINACA

5F-AB-PINACA is an indazole-based synthetic cannabinoid that is derived from a series of compounds originally developed by Pfizer in 2009 as an analgesic medication, and has been sold online as a designer drug.[1][2]

Not to be confused with 5F-APINACA.
5F-AB-PINACA
Legal status
Legal status
  • CA: Schedule II
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • UK: Class B
  • US: Schedule I
  • Illegal in China and Singapore
Identifiers
IUPAC name
  • N-[(2S)-1-Amino-3-methyl-1-oxobutan-2-yl]-1-(5-fluoropentyl)indazole-3-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H25FN4O2
Molar mass348.422 g·mol−1
3D model (JSmol)
SMILES
  • CC(C)[C@H](NC(=O)c1nn(CCCCCF)c2ccccc12)C(N)=O
InChI
  • InChI=1S/C18H25FN4O2/c1-12(2)15(17(20)24)21-18(25)16-13-8-4-5-9-14(13)23(22-16)11-7-3-6-10-19/h4-5,8-9,12,15H,3,6-7,10-11H2,1-2H3,(H2,20,24)(H,21,25)/t15-/m0/s1
  • Key:WCBYXIBEPFZUBG-HNNXBMFYSA-N

5F-AB-PINACA has been reported to be a potent agonist of the CB1 receptor and CB2 receptor with EC50 values of 0.48 nM and 2.6 nM respectively.[3] Its metabolism has been described in literature.[4][5]

Legality

China

As of October 2015 5F-AB-PINACA is a controlled substance in China.[6]

Germany

5F-AB-PINACA is an Anlage II controlled substance in Germany as of May 2015.[7]

Singapore

It is also controlled under the Fifth Schedule of the Misuse of Drugs Act (MDA) in Singapore as of May 2015.[8]

See also

References
  1. WO 2009106980, Buchler I, Hayes M, Hegde S, Hockerman S, Jones D, Kortum S, Rico J, Tenbrink R, Wu KK, "Indazole derivatives", published 2009-09-03, assigned to Pfizer
  2. "5F-AB-PINACA". Cayman Chemical. Retrieved 5 July 2015.
  3. Banister SD, Moir M, Stuart J, Kevin RC, Wood KE, Longworth M, et al. (September 2015). "Pharmacology of Indole and Indazole Synthetic Cannabinoid Designer Drugs AB-FUBINACA, ADB-FUBINACA, AB-PINACA, ADB-PINACA, 5F-AB-PINACA, 5F-ADB-PINACA, ADBICA, and 5F-ADBICA". ACS Chemical Neuroscience. 6 (9): 1546–59. doi:10.1021/acschemneuro.5b00112. PMID 26134475.
  4. Wohlfarth A, Castaneto MS, Zhu M, Pang S, Scheidweiler KB, Kronstrand R, Huestis MA (May 2015). "Pentylindole/Pentylindazole Synthetic Cannabinoids and Their 5-Fluoro Analogs Produce Different Primary Metabolites: Metabolite Profiling for AB-PINACA and 5F-AB-PINACA". The AAPS Journal. 17 (3): 660–77. doi:10.1208/s12248-015-9721-0. PMC 4406957. PMID 25721194.
  5. Jang M, Shin I, Kim J, Yang W (July 2015). "Simultaneous quantification of 37 synthetic cannabinoid metabolites in human urine by liquid chromatography-tandem mass spectrometry". Forensic Toxicology. 33 (2): 221–234. doi:10.1007/s11419-015-0265-x. S2CID 3038555.
  6. "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.
  7. "Gesetz über den Verkehr mit Betäubungsmitteln (Betäubungsmittelgesetz - BtMG) Anlage II (zu § 1 Abs. 1) (verkehrsfähige, aber nicht verschreibungsfähige Betäubungsmittel)" (in German). Retrieved 5 July 2015.
  8. "CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. Archived from the original on 15 July 2015. Retrieved 24 July 2015.
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