5F-AB-FUPPYCA

5F-AB-FUPPYCA
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics); CA: Schedule II; DE: NpSG (Industrial and scientific use only); UK: Under Psychoactive Substances Act;
Identifiers
	IUPAC name N-(1-Amino-3-methyl-1-oxobutan-2-yl)-1-(5-fluoropentyl)-5-(4-fluorophenyl)-1H-pyrazole-3-carboxamide;
CAS Number	2044702-46-5 ;
PubChem CID	129317827;
ChemSpider	58191440;
UNII	2G6G797F5B;
Chemical and physical data
Formula	C20H26F2N4O2
Molar mass	392.451 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES NC(C(C(C)C)NC(=O)C1=NN(C(=C1)C1=CC=C(C=C1)F)CCCCCF)=O;
	InChI InChI=1/C20H26F2N4O2/c1-13(2)18(19(23)27)24-20(28)16-12-17(14-6-8-15(22)9-7-14)26(25-16)11-5-3-4-10-21/h6-9,12-13,18H,3-5,10-11H2,1-2H3,(H2,23,27)(H,24,28)/f/h24H,23H2; Key:GSXRDTDYPSATDE-UHFFFAOYSA-N;

5F-AB-FUPPYCA (also known as AZ-037) is a pyrazole-based synthetic cannabinoid that is presumed to be an agonist of the CB₁ receptor and has been sold online as a designer drug.^[2]^[3] It was first detected by the EMCDDA as part of a seizure of 540 g white powder in France in February 2015.^[4]

The name AZ-037 is also used as a synonym for its structural isomer 5-fluoro-3,5-AB-PFUPPYCA.^[5] Thus AZ-037 is being used as a synonym for two different compounds.

5-fluoro-3,5-AB-PFUPPYCA has been detected in synthetic cannabinoid smoke blends in the USA as early as December 30, 2021, along with ADB-BUTINACA, MDA-19 (BZO-HEXOXIZID) and MDMB-4en-PINACA.^[6]

5-fluoro-AB-PFUPPYCA contains some similar structural elements to other synthetic cannabinoids such as AB-CHFUPYCA, JWH-307, JWH-030, JWH-147, AB-PINACA. It may be considered an analog of the traditional pyrazole cannabinoid receptor 1 antagonist rimonabant. The pharmacological properties of 5F-AB-FUPPYCA have not been studied.

Legality

In the United States, 5F-AB-FUPPYCA is unscheduled at the federal level as of May 22, 2023. It's possible that it may be considered under the federal analogue act as a functional analog due to pharmacology or as a distant structural analog of JWH-307.

North Dakota has placed 5F-AB-FUPPYCA (N-(1-carbamoyl-2-methyl-propyl)-2-(5-fluoropentyl)-5-(4-fluorophenyl)pyrazole-3-carboxamide) into Schedule I status on 04/27/2023. However, this did not include structural substitutions it gave to other cannabinoid structural classes. As such does not include other pyrazoles analogs such as the non-fluorinated AB-FUPPYCA analog.^[7]

References

^ 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.
^ Girreser U, Rösner P, Vasilev A (July 2016). "Structure elucidation of the designer drug N-(1-amino-3,3-dimethyl-1-oxobutan-2-yl)-1-(5-fluoropentyl)-3-(4-fluorophenyl)-pyrazole-5-carboxamide and the relevance of predicted (13) C NMR shifts - a case study". Drug Testing and Analysis. 8 (7): 668–75. doi:10.1002/dta.1820. PMID 26012418.
^ 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): 1241–54. doi:10.1021/acschemneuro.6b00137. PMID 27421060.
^ "2015. ÉVI EURÓPAI KÁBÍTÓSZER - JELENTÉS - A MONITOROZÁS 20 ÉVE" (PDF). Hungarian National Focal Point (NFP). June 2015. Archived (PDF) from the original on 24 July 2015. Retrieved 23 July 2015.
^ "5-fluoro-3,5-AB-PFUPPYCA". Cayman Chemical Company. Archived from the original on 3 June 2016. Retrieved 11 February 2016.
^ "Test Details : Result #11908 - Plant Material, 11908". DrugsData.org (was EcstasyData). Archived from the original on 2022-04-16. Retrieved 2022-04-17.
^ "AN ACT to amend and reenact sections 19-03.1-05, 19-03.1-11, and 19-03.1-13 of the North Dakota Century Code, relating to the scheduling of controlled substances; and to declare an emergency" (PDF). Sixty-eighth Legislative Assembly of North Dakota in Regular Session. 3 January 2023.

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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] Girreser U, Rösner P, Vasilev A (July 2016). "Structure elucidation of the designer drug N-(1-amino-3,3-dimethyl-1-oxobutan-2-yl)-1-(5-fluoropentyl)-3-(4-fluorophenyl)-pyrazole-5-carboxamide and the relevance of predicted (13) C NMR shifts - a case study". Drug Testing and Analysis. 8 (7): 668–75. doi:10.1002/dta.1820. PMID 26012418.

[3] 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): 1241–54. doi:10.1021/acschemneuro.6b00137. PMID 27421060.

[4] "2015. ÉVI EURÓPAI KÁBÍTÓSZER - JELENTÉS - A MONITOROZÁS 20 ÉVE" (PDF). Hungarian National Focal Point (NFP). June 2015. Archived (PDF) from the original on 24 July 2015. Retrieved 23 July 2015.

[5] "5-fluoro-3,5-AB-PFUPPYCA". Cayman Chemical Company. Archived from the original on 3 June 2016. Retrieved 11 February 2016.

[6] "Test Details : Result #11908 - Plant Material, 11908". DrugsData.org (was EcstasyData). Archived from the original on 2022-04-16. Retrieved 2022-04-17.

[7] "AN ACT to amend and reenact sections 19-03.1-05, 19-03.1-11, and 19-03.1-13 of the North Dakota Century Code, relating to the scheduling of controlled substances; and to declare an emergency" (PDF). Sixty-eighth Legislative Assembly of North Dakota in Regular Session. 3 January 2023.

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Legality

See also

References