5F-AB-PINACA

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	1800101-60-3;
PubChem CID	91936927;
ChemSpider	29763723;
UNII	3L83B2298V;
CompTox Dashboard (EPA)	DTXSID401009970 ;
Chemical and physical data
Formula	C18H25FN4O2
Molar mass	348.422 g·mol−1
3D model (JSmol)	Interactive image;
	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 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]

Quick Facts Legal status, Identifiers ...

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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]

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]

[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.

[1] [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] [2]
"5F-AB-PINACA". Cayman Chemical. Retrieved 5 July 2015.

[3] [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] [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] [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] [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] [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] [8]
"CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. Archived from the original on 15 July 2015. Retrieved 24 July 2015.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

China

Germany

Singapore

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5F-AB-PINACA

China

Germany

Singapore

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Legality

See also

References

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	1800101-60-3
PubChem CID	91936927
ChemSpider	29763723
UNII	3L83B2298V
CompTox Dashboard (EPA)	DTXSID401009970
Chemical and physical data
Formula	C₁₈H₂₅FN₄O₂
Molar mass	348.422 g·mol⁻¹
3D model (JSmol)	Interactive image
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