CUMYL-PICA

CUMYL-PICA (SGT-56) is an indole-3-carboxamide based synthetic cannabinoid. It is the α,α-dimethylbenzyl analogue of SDB-006.[1] It was briefly sold in New Zealand during 2013 as an ingredient of at the time legal synthetic cannabis products, but the product containing CUMYL-BICA and CUMYL-PICA was denied an interim licensing approval under the Psychoactive Substances regulatory scheme, due to reports of adverse events in consumers.[2] CUMYL-PICA acts as an agonist for the cannabinoid receptors, with Ki values of 59.21 nM at CB1 and 136.38 nM at CB2 and EC50 values of 11.98 nM at CB1 and 16.2 nM at CB2.[3][4]

CUMYL-PICA
Legal status
Legal status
Identifiers
IUPAC name
  • 1-pentyl-N-(2-phenylpropan-2-yl)-1H-indole-3-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC23H28N2O
Molar mass348.490 g·mol−1
3D model (JSmol)
SMILES
  • O=C(NC(C)(C)C1=CC=CC=C1)C2=CN(CCCCC)C3=C2C=CC=C3
InChI
  • InChI=1S/C23H28N2O/c1-4-5-11-16-25-17-20(19-14-9-10-15-21(19)25)22(26)24-23(2,3)18-12-7-6-8-13-18/h6-10,12-15,17H,4-5,11,16H2,1-3H3,(H,24,26)
  • Key:RCXFMWJQOYCIQU-UHFFFAOYSA-N


See also

References
  1. Ametovski A, Macdonald C, Manning JJ, Haneef SA, Santiago M, Martin L, et al. (November 2020). "Exploring Stereochemical and Conformational Requirements at Cannabinoid Receptors for Synthetic Cannabinoids Related to SDB-006, 5F-SDB-006, CUMYL-PICA, and 5F-CUMYL-PICA". ACS Chemical Neuroscience. 11 (21): 3672–3682. doi:10.1021/acschemneuro.0c00591. PMID 33054155.
  2. "The Risk Assessment Score Table. New Zealand Ministry of Health, 27 September 2013" (PDF). Archived from the original (PDF) on 2014-01-08. Retrieved 2015-07-09.
  3. Gamage TF, Farquhar CE, Lefever TW, Marusich JA, Kevin RC, McGregor IS, et al. (May 2018). "Molecular and Behavioral Pharmacological Characterization of Abused Synthetic Cannabinoids MMB- and MDMB-FUBINACA, MN-18, NNEI, CUMYL-PICA, and 5-Fluoro-CUMYL-PICA". The Journal of Pharmacology and Experimental Therapeutics. 365 (2): 437–446. doi:10.1124/jpet.117.246983. PMC 5932312. PMID 29549157.
  4. WO 2014167530, Bowden MJ, Bernard WJ, "Cannabinoid compounds", published 11 April 2013
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