QUCHIC

QUCHIC
Legal status
Legal status	CA: Schedule II; DE: Anlage II (Authorized trade only, not prescriptible); NZ: Temporary Class; UK: Class B;
Identifiers
	IUPAC name 1-(cyclohexylmethyl)-1H-indole-3-carboxylic acid 8-quinolinyl ester;
CAS Number	1400742-42-8;
PubChem CID	71711120;
ChemSpider	29339967;
UNII	EUD4ZLB25R;
CompTox Dashboard (EPA)	DTXSID40856801 ;
Chemical and physical data
Formula	C25H24N2O2
Molar mass	384.479 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CCC(CC1)CN2C=C(C3=CC=CC=C32)C(=O)OC4=CC=CC5=C4N=CC=C5;
	InChI InChI=1S/C25H24N2O2/c28-25(29-23-14-6-10-19-11-7-15-26-24(19)23)21-17-27(16-18-8-2-1-3-9-18)22-13-5-4-12-20(21)22/h4-7,10-15,17-18H,1-3,8-9,16H2; Key:RHYGTJXOHOGQGI-UHFFFAOYSA-N;

QUCHIC (BB-22, SGT-32 or 1-(cyclohexylmethyl)-1H-indole-3-carboxylic acid 8-quinolinyl ester) is a designer drug offered by online vendors as a cannabimimetic agent, and was first detected being sold in synthetic cannabis products in Japan in early 2013,^[1] and subsequently also in New Zealand.^[2] The structure of QUCHIC appears to use an understanding of structure-activity relationships within the indole class of cannabimimetics, although its design origins are unclear. QUCHIC, along with QUPIC, represents a structurally unique synthetic cannabinoid chemotype since it contains an ester linker at the indole 3-position rather than the precedented ketone of JWH-018 and its analogues, or the amide of SDB-001 and its analogues.

Pharmacology

BB-22 acts as a full agonist with a binding affinity of 0.217nM at CB₁ and 0.338nM at CB₂ cannabinoid receptors.^[3]

References

^ Uchiyama N, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y (2013). "Two new-type cannabimimetic quinolinyl carboxylates, QUPIC and QUCHIC, two new cannabimimetic carboxamide derivatives, ADB-FUBINACA and ADBICA, and five synthetic cannabinoids detected with a thiophene derivative α-PVT and an opioid receptor agonist AH-7921 identified in illegal products". Forensic Toxicology. 31 (2): 223–240. doi:10.1007/s11419-013-0182-9. S2CID 1279637.
^ Dunne bans further two substances found in K2. Press Release: New Zealand Government. Tuesday, 30 April 2013
^ Hess C, Schoeder CT, Pillaiyar T, Madea B, Müller CE (1 July 2016). "Pharmacological evaluation of synthetic cannabinoids identified as constituents of spice". Forensic Toxicology. 34 (2): 329–343. doi:10.1007/s11419-016-0320-2. PMC 4929166. PMID 27429655.

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[1] Uchiyama N, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y (2013). "Two new-type cannabimimetic quinolinyl carboxylates, QUPIC and QUCHIC, two new cannabimimetic carboxamide derivatives, ADB-FUBINACA and ADBICA, and five synthetic cannabinoids detected with a thiophene derivative α-PVT and an opioid receptor agonist AH-7921 identified in illegal products". Forensic Toxicology. 31 (2): 223–240. doi:10.1007/s11419-013-0182-9. S2CID 1279637.

[2] Dunne bans further two substances found in K2. Press Release: New Zealand Government. Tuesday, 30 April 2013

[3] Hess C, Schoeder CT, Pillaiyar T, Madea B, Müller CE (1 July 2016). "Pharmacological evaluation of synthetic cannabinoids identified as constituents of spice". Forensic Toxicology. 34 (2): 329–343. doi:10.1007/s11419-016-0320-2. PMC 4929166. PMID 27429655.

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Pharmacology

See also

References