View source for Chemistry:5F-AB-FUPPYCA

{{Short description|Chemical compound}}
{{Drugbox
| IUPAC_name = ''N''-(1-Amino-3-methyl-1-oxobutan-2-yl)-1-(5-fluoropentyl)-5-(4-fluorophenyl)-1''H''-pyrazole-3-carboxamide
| image = 5F-AB-FUPPYCA.svg

<!--Clinical data-->
| tradename =  
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B            / C / D / X -->
| pregnancy_category =  
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_BR = F2
| legal_CA = Schedule II
| legal_DE = NpSG
| legal_UK = PSA
| legal_US = 
| legal_NZ = 
| routes_of_administration =

<!--Pharmacokinetic data-->
| bioavailability =  
| protein_bound =  
| metabolism =  
| elimination_half-life =  
| excretion =

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 2044702-46-5
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2G6G797F5B
| ATC_prefix =  
| ATC_suffix =  
| PubChem =  129317827
| ChemSpiderID      = 58191440
| smiles            = NC(C(C(C)C)NC(=O)C1=NN(C(=C1)C1=CC=C(C=C1)F)CCCCCF)=O
| StdInChI          = 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
| StdInChIKey       = GSXRDTDYPSATDE-UHFFFAOYSA-N

<!--Chemical data-->
| C=20 | H=26 | F=2 | N=4 | O=2
}}

'''5F-AB-FUPPYCA''' (also known as '''AZ-037''') is a [[Chemistry:Pyrazole|pyrazole]]-based synthetic cannabinoid that is presumed to be an [[Biology:Agonist|agonist]] of the CB<sub>1</sub> receptor and has been sold online as a [[Chemistry:Designer drug|designer drug]].<ref>{{cite journal | vauthors = Girreser U, Rösner P, Vasilev A | title = 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 | journal = Drug Testing and Analysis | volume = 8 | issue = 7 | pages = 668–75 | date = July 2016 | pmid = 26012418 | doi = 10.1002/dta.1820 }}</ref><ref>{{cite journal | vauthors = Banister SD, Longworth M, Kevin R, Sachdev S, Santiago M, Stuart J, Mack JB, Glass M, McGregor IS, Connor M, Kassiou M | display-authors = 6 | title = Pharmacology of Valinate and tert-Leucinate Synthetic Cannabinoids 5F-AMBICA, 5F-AMB, 5F-ADB, AMB-FUBINACA, MDMB-FUBINACA, MDMB-CHMICA, and Their Analogues | journal = ACS Chemical Neuroscience | volume = 7 | issue = 9 | pages = 1241–54 | date = September 2016 | pmid = 27421060 | doi = 10.1021/acschemneuro.6b00137 }}</ref> It was first detected by the EMCDDA as part of a seizure of 540&nbsp;g white powder in France in February 2015.<ref>{{cite web | url=http://drogfokuszpont.hu/wp-content/uploads/NFP_hirlevel_2015_junius.pdf | title=2015. ÉVI EURÓPAI KÁBÍTÓSZER - JELENTÉS - A MONITOROZÁS 20 ÉVE | publisher=Hungarian National Focal Point (NFP) | date=June 2015 | access-date=23 July 2015 | archive-date=24 July 2015 | archive-url=https://web.archive.org/web/20150724022838/http://drogfokuszpont.hu/wp-content/uploads/NFP_hirlevel_2015_junius.pdf | url-status=live }}</ref>

The name AZ-037 is also used as a synonym for its structural isomer 5-fluoro-3,5-AB-PFUPPYCA.<ref>{{cite web | url=https://www.caymanchem.com/product/17181 | title=5-fluoro-3,5-AB-PFUPPYCA | publisher=Cayman Chemical Company | access-date=11 February 2016 | archive-date=3 June 2016 | archive-url=https://web.archive.org/web/20160603030151/https://www.caymanchem.com/product/17181 | url-status=live }}</ref> 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, [[Chemistry:MDA-19|MDA-19]] (BZO-HEXOXIZID) and [[Chemistry:MDMB-4en-PINACA|MDMB-4en-PINACA]].<ref>{{Cite web |url=https://drugsdata.org/view.php?id=11908 |title=Test Details : Result #11908 - Plant Material, 11908 |publisher=DrugsData.org (was EcstasyData) |access-date=2022-04-17 |archive-date=2022-04-16 |archive-url=https://web.archive.org/web/20220416034503/https://drugsdata.org/view.php?id=11908 |url-status=live }}</ref>

5-fluoro-AB-PFUPPYCA contains some similar structural elements to other synthetic cannabinoids such as [[Chemistry:AB-CHFUPYCA|AB-CHFUPYCA]], [[Chemistry:JWH-307|JWH-307]], [[Chemistry:JWH-030|JWH-030]], [[Chemistry:JWH-147|JWH-147]], [[Chemistry:AB-PINACA|AB-PINACA]]. It may be considered an analog of the traditional [[Chemistry:Pyrazole|pyrazole]] cannabinoid receptor 1 antagonist [[Chemistry:Rimonabant|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 [[Chemistry:JWH-307|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.<ref>{{cite web | title = 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. | url = https://www.ndlegis.gov/prod/assembly/68-2023/regular/documents/23-8099-04000.pdf | work = Sixty-eighth Legislative Assembly of North Dakota in Regular Session | date = 3 January 2023 }}</ref>

== See also ==
{{div col|colwidth=30em}}
* [[Chemistry:AB-CHFUPYCA|AB-CHFUPYCA]]
* [[Chemistry:AM-6545|AM-6545]]
* [[Chemistry:TM-38837|TM-38837]]
* [[Chemistry:Rimonabant|Rimonabant]]
* [[Chemistry:JWH-307|JWH-307]]
* [[Chemistry:JWH-147|JWH-147]]
* [[Chemistry:JWH-030|JWH-030]]
* [[Chemistry:AB-FUBINACA|AB-FUBINACA]]
* [[Chemistry:ADB-FUBINACA|ADB-FUBINACA]]
* [[Chemistry:AMB-FUBINACA|AMB-FUBINACA]]
* [[Chemistry:APP-FUBINACA|APP-FUBINACA]]
* [[Chemistry:MDA-19|MDA-19]]
* [[Chemistry:FUB-144|FUB-144]]
* [[Chemistry:FUB-APINACA|FUB-APINACA]]
* [[Chemistry:FUB-JWH-018|FUB-JWH-018]]
* [[Chemistry:FDU-PB-22|FDU-PB-22]]
* [[Chemistry:FUB-PB-22|FUB-PB-22]]
* [[Chemistry:MDMB-FUBICA|MDMB-FUBICA]]
* [[Chemistry:MDMB-FUBINACA|MDMB-FUBINACA]]
{{Div col end}}

== References ==
{{reflist}}

{{Cannabinoids}}

[[Category:Cannabinoids]]
[[Category:Designer drugs]]
[[Category:Fluoroarenes]]
[[Category:Pyrazoles]]
[[Category:Pyrazolecarboxamides]]
[[Category:Organofluorides]]



{{Sourceattribution|5F-AB-FUPPYCA}}