Chemical compound
Pharmaceutical compound
5F-CUMYL-P7AICA Legal status
1-(5-Fluoropentyl)-N-(2-phenylpropan-2-yl)pyrrolo[2,3-b]pyridine-3-carboxamide
CAS Number PubChem CID ChemSpider UNII Formula C 22 H 26 F N 3 O Molar mass −1 3D model (JSmol )
FCCCCCn1cc(c3cccnc13)C(=O)NC(C)(C)c2ccccc2
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] EMCDDA in February 2015.[ 7]
See also
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 .
Phytocannabinoids comparison )
Cannabibutols Cannabichromenes Cannabicyclols Cannabidiols Cannabielsoins Cannabigerols Cannabiphorols Cannabinols Cannabitriols Cannabivarins Delta-8-tetrahydrocannabinols Delta-9-tetrahydrocannabinols Delta-10-Tetrahydrocannabinols Miscellaneous cannabinoids Active metabolites
Endocannabinoids Synthetic
Classical cannabinoids Non-classical Adamantoylindoles Benzimidazoles Benzoylindoles Cyclohexylphenols Eicosanoids Indazole-3- Indole-3-carboxamides Indole-3-carboxylates Naphthoylindazoles Naphthoylindoles Naphthoylpyrroles Naphthylmethylindenes Naphthylmethylindoles Phenylacetylindoles Pyrazolecarboxamides Tetramethylcyclo- Tetramethylcyclo- Others
Allosteric CBR Tooltip Cannabinoid receptor ligands Endocannabinoid (inactivation inhibitors) Anticannabinoids (antagonists/inverse
Receptor (ligands )
CB1 Tooltip Cannabinoid receptor type 1
Agonists(abridged,full list ) Inverse agonists Antagonists
CB2 Tooltip Cannabinoid receptor type 2
Agonists
2-AG 2-AGE (noladin ether) 3,3'-Diindolylmethane 4-O-Methylhonokiol α-Amyrin · β-Amyrin A-796,260 A-834,735 A-836,339 AM-1172 AM-1221 AM-1235 AM-1241 AM-2232 Anandamide AZ-11713908 Cannabinol Caryophyllene CB-13 CBS-0550 CP 55,940 GW-405,833 (L-768,242) GW-842,166X HU-308 JTE 7-31 JWH-007 JWH-015 JWH-018 JWH-73 JWH-133 L-759,633 L-759,656 Lenabasum (anabasum) Magnolol MDA-19 Nabitan NADA Olorinab (APD-371) PF-03550096 S-444,823 SER-601 Serinolamide A UR-144 Tedalinab THC (dronabinol) THCV Tetrahydromagnolol Virodhamine Antagonists
NAGly GPR18 )
GPR55
GPR119
Transporter (modulators )
eCBTs Tooltip Endocannabinoid transporter
Enzyme (modulators )
Others
Others: 2-PG (directly potentiates activity of 2-AG at CB1 receptor) ARN-272 (FAAH-like anandamide transporter inhibitor)
