CUMYL-PICA

CUMYL-PICA
Legal status
Legal status	CA: Schedule II; DE: NpSG (Industrial and scientific use only); UK: Class B;
Identifiers
	IUPAC name 1-pentyl-N-(2-phenylpropan-2-yl)-1H-indole-3-carboxamide;
CAS Number	1400742-32-6 ;
PubChem CID	86273678;
ChemSpider	34450887;
UNII	H4APZ90T9U;
CompTox Dashboard (EPA)	DTXSID601017202 ;
Chemical and physical data
Formula	C23H28N2O
Molar mass	348.490 g·mol−1
3D model (JSmol)	Interactive image;
	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;

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 K_i 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]

References

^ 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. S2CID 222821806.
^ "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.
^ 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.
^ WO 2014167530, Bowden MJ, Bernard WJ, "Cannabinoid compounds", published 11 April 2013

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[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. S2CID 222821806.

[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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See also

References