THC Science

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[edit]

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[edit]

^ 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.

[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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@@ Line 1: / Line 1: @@
+{{Short description|Chemical compound}}
 {{Drugbox
-| IUPAC_name = N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(5-fluoropentyl)-5-(4-fluorophenyl)-1H-pyrazole-3-carboxamide
+| 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.png
+| image = 5F-AB-FUPPYCA.svg
 <!--Clinical data-->
@@ Line 9: / Line 10: @@
 | pregnancy_category =
 | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
+| legal_BR = F2
-| legal_CA = <!--             / Schedule I, II, III, IV, V, VI, VII, VIII -->
+| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-07-25}}</ref>
-| legal_UK = <!-- GSL         / P       / POM / CD / Class A, B, C -->
+| legal_CA = Schedule II
+| legal_DE = NpSG
+| legal_UK = PSA
 | legal_US =
 | legal_NZ =
@@ Line 23: / Line 27: @@
 <!--Identifiers-->
-| CAS_number_Ref =
+| CAS_number_Ref = {{cascite|correct|CAS}}
-| CAS_number =
+| CAS_number = 2044702-46-5
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = 2G6G797F5B
 | ATC_prefix =
 | ATC_suffix =
-| PubChem =
+| PubChem =  129317827
-| ChemSpiderID      =
+| 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
@@ Line 34: / Line 40: @@
 <!--Chemical data-->
-| C=20 | H=26 | F=1 | N=4 | O=2
+| C=20 | H=26 | F=2 | N=4 | O=2
-| molecular_weight = 392,45 g/mol
 }}
-'''5F-AB-FUPPYCA''' (also known as '''AZ-037''') is a [[pyrazole]]-based [[synthetic cannabinoid]] that is presumed to be a potent [[agonist]] of the [[CB1 receptor|CB<sub>1</sub> receptor]] and has been sold online as a [[designer drug]].<ref>{{cite journal | url=http://onlinelibrary.wiley.com/doi/10.1002/dta.1820/abstract | 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 13C NMR shifts – a case study | author=Ulrich Girreser, Peter Rösner, Andrej Vasilev | journal=Drug Testing and Analysis |date=May 2015  | doi=10.1002/dta.1820 | pmid=26012418}}</ref> It was first detected by the [[European Monitoring Centre for Drugs and Drug Addiction|EMCDDA]] as part of a seizure of 540g 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 | accessdate=23 July 2015}}</ref>
+'''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|CB<sub>1</sub> receptor]] and has been sold online as a [[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 [[European Monitoring Centre for Drugs and Drug Addiction|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.
-==See also==
+-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]].<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>
+-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.<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}}
+* [[AB-CHFUPYCA]]
+* [[AM-6545]]
+* [[TM-38837]]
+* [[Rimonabant]]
+* [[JWH-307]]
+* [[JWH-147]]
+* [[JWH-030]]
 * [[AB-FUBINACA]]
 * [[ADB-FUBINACA]]
 * [[AMB-FUBINACA]]
 * [[APP-FUBINACA]]
-* [[FDU-NNE1]]
+* [[MDA-19]]
 * [[FUB-144]]
 * [[FUB-APINACA]]
 * [[FUB-JWH-018]]
-* [[FUB-NNE1]]
 * [[FDU-PB-22]]
 * [[FUB-PB-22]]
@@ Line 57: / Line 80: @@
 {{Div col end}}
-==References==
+== References ==
 {{reflist}}
@@ Line 64: / Line 87: @@
 [[Category:Cannabinoids]]
 [[Category:Designer drugs]]
-[[Category:Organofluorides]]
+[[Category:Fluoroarenes]]
 [[Category:Pyrazoles]]
 [[Category:Pyrazolecarboxamides]]
+[[Category:Organofluorides]]

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Latest revision as of 02:38, 28 August 2023

Legality[edit]

See also[edit]

References[edit]

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Legal status

Legal status	BR: Class F2 (Prohibited psychotropics)^[1] 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^Y
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