5F-CUMYL-P7AICA

5F-CUMYL-P7AICA
Legal status
Legal status	CA: Schedule II; DE: NpSG (Industrial and scientific use only); UK: Under Psychoactive Substances Act; US: Schedule I;
Identifiers
	IUPAC name 1-(5-Fluoropentyl)-N-(2-phenylpropan-2-yl)pyrrolo[2,3-b]pyridine-3-carboxamide;
CAS Number	2171492-36-5;
PubChem CID	129532613;
ChemSpider	68028038;
UNII	V3J3TQ3UPP;
Chemical and physical data
Formula	C22H26FN3O
Molar mass	367.468 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES FCCCCCn1cc(c3cccnc13)C(=O)NC(C)(C)c2ccccc2;
	InChI InChI=1S/C22H26FN3O/c1-22(2,17-10-5-3-6-11-17)25-21(27)19-16-26(15-8-4-7-13-23)20-18(19)12-9-14-24-20/h3,5-6,9-12,14,16H,4,7-8,13,15H2,1-2H3,(H,25,27); Key:MXJYOUMYJGNQEY-UHFFFAOYSA-N;

5F-CUMYL-P7AICA (also known as CUMYL-5F-P7AICA or SGT-263) is a pyrrolo[2,3-b]pyridine-3-carboxamide based synthetic cannabinoid that has been sold as a designer drug.^[1]^[2]^[3]^[4]^[5]^[6] It was first identified by the EMCDDA in February 2015.^[7]

References

^ Ernst L, Brandhorst K, Papke U, Altrogge A, Zodel S, Langer N, Beuerle T (August 2017). "Identification and quantification of synthetic cannabinoids in 'spice-like' herbal mixtures: Update of the German situation in early 2017". Forensic Science International. 277: 51–58. doi:10.1016/j.forsciint.2017.05.019. PMID 28601726.
^ Staeheli SN, Poetzsch M, Veloso VP, Bovens M, Bissig C, Steuer AE, Kraemer T (January 2018). "In vitro metabolism of the synthetic cannabinoids CUMYL-PINACA, 5F-CUMYL-PINACA, CUMYL-4CN-BINACA, 5F-CUMYL-P7AICA and CUMYL-4CN-B7AICA". Drug Testing and Analysis. 10 (1): 148–157. doi:10.1002/dta.2298. PMID 28885775.
^ Bovens M, Bissig C, Staeheli SN, Poetzsch M, Pfeiffer B, Kraemer T (December 2017). "Structural characterization of the new synthetic cannabinoids CUMYL-PINACA, 5F-CUMYL-PINACA, CUMYL-4CN-BINACA, 5F-CUMYL-P7AICA and CUMYL-4CN-B7AICA". Forensic Science International. 281: 98–105. doi:10.1016/j.forsciint.2017.10.020. PMID 29125990.
^ Banister SD, Adams A, Kevin RC, Macdonald C, Glass M, Boyd R, Connor M, McGregor IS, Havel CM, Bright SJ, Ventura Vilamala M, Gil Lladanosa C, Barratt MJ, Gerona RR (August 2018). "Synthesis and pharmacology of new psychoactive substance 5F-CUMYL-P7AICA, a scaffold-hopping analog of synthetic cannabinoid receptor agonists 5F-CUMYL-PICA and 5F-CUMYL-PINACA". Drug Testing and Analysis. 11 (2): 279–291. doi:10.1002/dta.2491. hdl:1959.4/unsworks_58933. PMID 30151911. S2CID 52100276.
^ Walle N, Nordmeier F, Doerr AA, Peters B, Laschke MW, Menger MD, Schmidt PH, Meyer MR, Schaefer N (July 2020). "Comparison of in vitro and in vivo models for the elucidation of metabolic patterns of 7-azaindole-derived synthetic cannabinoids exemplified using cumyl-5F-P7AICA". Drug Testing and Analysis. 13 (1): 74–90. doi:10.1002/dta.2899. PMID 32678962.
^ Gatch MB, Tourigny A, Shetty RA, Forster MJ (February 2021). "Behavioral pharmacology of five novel synthetic cannabinoids". Behavioural Pharmacology. 33 (2&3): 175–183. doi:10.1097/FBP.0000000000000618. PMC 8364570. PMID 33595956.
^ "Annual Report on the implementation of Council Decision 2005/387/JHA" (PDF). Europol. 2015.
^ ^a ^b ^c Cannaert A, Sparkes E, Pike E, Luo JL, Fang A, Kevin RC, Ellison R, Gerona R, Banister SD, Stove CP (2020). "Synthesis and in Vitro Cannabinoid Receptor 1 Activity of Recently Detected Synthetic Cannabinoids 4F-MDMB-BICA, 5F-MPP-PICA, MMB-4en-PICA, CUMYL-CBMICA, ADB-BINACA, APP-BINACA, 4F-MDMB-BINACA, MDMB-4en-PINACA, A-CHMINACA, 5F-AB-P7AICA, 5F-MDMB-P7AICA, and 5F-AP7AICA". ACS Chemical Neuroscience. 11 (24): 4434–4446. doi:10.1021/acschemneuro.0c00644. PMID 33253529. S2CID 227246346.

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[1] Ernst L, Brandhorst K, Papke U, Altrogge A, Zodel S, Langer N, Beuerle T (August 2017). "Identification and quantification of synthetic cannabinoids in 'spice-like' herbal mixtures: Update of the German situation in early 2017". Forensic Science International. 277: 51–58. doi:10.1016/j.forsciint.2017.05.019. PMID 28601726.

[2] Staeheli SN, Poetzsch M, Veloso VP, Bovens M, Bissig C, Steuer AE, Kraemer T (January 2018). "In vitro metabolism of the synthetic cannabinoids CUMYL-PINACA, 5F-CUMYL-PINACA, CUMYL-4CN-BINACA, 5F-CUMYL-P7AICA and CUMYL-4CN-B7AICA". Drug Testing and Analysis. 10 (1): 148–157. doi:10.1002/dta.2298. PMID 28885775.

[3] Bovens M, Bissig C, Staeheli SN, Poetzsch M, Pfeiffer B, Kraemer T (December 2017). "Structural characterization of the new synthetic cannabinoids CUMYL-PINACA, 5F-CUMYL-PINACA, CUMYL-4CN-BINACA, 5F-CUMYL-P7AICA and CUMYL-4CN-B7AICA". Forensic Science International. 281: 98–105. doi:10.1016/j.forsciint.2017.10.020. PMID 29125990.

[4] Banister SD, Adams A, Kevin RC, Macdonald C, Glass M, Boyd R, Connor M, McGregor IS, Havel CM, Bright SJ, Ventura Vilamala M, Gil Lladanosa C, Barratt MJ, Gerona RR (August 2018). "Synthesis and pharmacology of new psychoactive substance 5F-CUMYL-P7AICA, a scaffold-hopping analog of synthetic cannabinoid receptor agonists 5F-CUMYL-PICA and 5F-CUMYL-PINACA". Drug Testing and Analysis. 11 (2): 279–291. doi:10.1002/dta.2491. hdl:1959.4/unsworks_58933. PMID 30151911. S2CID 52100276.

[pmid32678962-5] Walle N, Nordmeier F, Doerr AA, Peters B, Laschke MW, Menger MD, Schmidt PH, Meyer MR, Schaefer N (July 2020). "Comparison of in vitro and in vivo models for the elucidation of metabolic patterns of 7-azaindole-derived synthetic cannabinoids exemplified using cumyl-5F-P7AICA". Drug Testing and Analysis. 13 (1): 74–90. doi:10.1002/dta.2899. PMID 32678962.

[pmid33595956-6] Gatch MB, Tourigny A, Shetty RA, Forster MJ (February 2021). "Behavioral pharmacology of five novel synthetic cannabinoids". Behavioural Pharmacology. 33 (2&3): 175–183. doi:10.1097/FBP.0000000000000618. PMC 8364570. PMID 33595956.

[7] "Annual Report on the implementation of Council Decision 2005/387/JHA" (PDF). Europol. 2015.

[cannaert-8] Cannaert A, Sparkes E, Pike E, Luo JL, Fang A, Kevin RC, Ellison R, Gerona R, Banister SD, Stove CP (2020). "Synthesis and in Vitro Cannabinoid Receptor 1 Activity of Recently Detected Synthetic Cannabinoids 4F-MDMB-BICA, 5F-MPP-PICA, MMB-4en-PICA, CUMYL-CBMICA, ADB-BINACA, APP-BINACA, 4F-MDMB-BINACA, MDMB-4en-PINACA, A-CHMINACA, 5F-AB-P7AICA, 5F-MDMB-P7AICA, and 5F-AP7AICA". ACS Chemical Neuroscience. 11 (24): 4434–4446. doi:10.1021/acschemneuro.0c00644. PMID 33253529. S2CID 227246346.

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See also

References