QUCHIC

{{Short description|Chemical compound}}

{{Drugbox

| Verifiedfields =

| verifiedrevid =

| IUPAC_name = 1-(cyclohexylmethyl)-1H-indole-3-carboxylic acid 8-quinolinyl ester

| image = BB-22.png

| image_class = skin-invert-image

| width = 200

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_DE = Anlage II

| legal_CA = Schedule II

| legal_UK = Class B

| legal_US =

| legal_NZ = Temporary Class

| routes_of_administration =

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

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| CAS_number_Ref =

| CAS_number = 1400742-42-8

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = EUD4ZLB25R

| ATC_prefix =

| ATC_suffix =

| PubChem = 71711120

| DrugBank_Ref =

| DrugBank =

| ChemSpiderID = 29339967

| smiles = C1CCC(CC1)CN2C=C(C3=CC=CC=C32)C(=O)OC4=CC=CC5=C4N=CC=C5

| StdInChI = 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

| StdInChIKey = RHYGTJXOHOGQGI-UHFFFAOYSA-N

| C=25 | H=24 | N=2 | O=2

}}

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,{{Cite journal | vauthors = Uchiyama N, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y | title = 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 | doi = 10.1007/s11419-013-0182-9 | journal = Forensic Toxicology | volume = 31 | issue = 2 | pages = 223–240 | year = 2013 | s2cid = 1279637 }} and subsequently also in New Zealand.[http://www.scoop.co.nz/stories/PA1304/S00561/dunne-bans-further-two-substances-found-in-k2.htm Dunne bans further two substances found in K2. Press Release: New Zealand Government. Tuesday, 30 April 2013] 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.{{cite journal | vauthors = Hess C, Schoeder CT, Pillaiyar T, Madea B, Müller CE | title = Pharmacological evaluation of synthetic cannabinoids identified as constituents of spice | journal = Forensic Toxicology | volume = 34 | issue = 2 | pages = 329–343 | date = 1 July 2016 | pmid = 27429655 | pmc = 4929166 | doi = 10.1007/s11419-016-0320-2 }}

See also

References