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QUCHMIC

QUCHMIC
Clinical data
Other namesBB-22; SGT-32; quinolin-8-yl 1-cyclohexylmethyl-1H-indole-3-8-carboxylate
Legal status
Legal status
Identifiers
  • 1-(cyclohexylmethyl)-1H-indole-3-carboxylic acid 8-quinolinyl ester
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H24N2O2
Molar mass384.479 g·mol−1
3D model (JSmol)
  • C1CCC(CC1)CN2C=C(C3=CC=CC=C32)C(=O)OC4=CC=CC5=C4N=CC=C5
  • 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

QUCHMIC (named using EMCDDA naming standards,[1] but regularly mis-named QUCHIC[nb 1]), also known as BB-22, SGT-32, or quinolin-8-yl 1-cyclohexylmethyl-1H-indole-3-8-carboxylate, 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,[2] and subsequently also in New Zealand.[3]

The structure of QUCHMIC appears to use an understanding of structure-activity relationships within the indole class of cannabimimetics, although its design origins are unclear. QUCHMIC, along with QUPIC, QUFUBIC, 2F-QMPSB and NA-PINAC, represent a structurally unusual synthetic cannabinoid chemotype since they contain 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

QUCHMIC acts as a full agonist with a binding affinity of 0.217 nM at CB1 and 0.338 nM at CB2 cannabinoid receptors.[4]

See also

Notes

  1. ^ The compound QUCHIC (quinolin-8-yl 1-cyclohexyl-1H-indole-3-8-carboxylate) has never been detected

References

  1. ^ Pulver B, Fischmann S, Gallegos A, Christie R (March 2023). "EMCDDA framework and practical guidance for naming synthetic cannabinoids". Drug Testing and Analysis. 15 (3): 255–276. doi:10.1002/dta.3403. PMID 36346325.
  2. ^ 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.
  3. ^ Dunne bans further two substances found in K2. Press Release: New Zealand Government. Tuesday, 30 April 2013
  4. ^ 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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