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QMPSB

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
QMPSB
Legal status
Legal status
Identifiers
  • 8-quinolinyl 4-methyl-3-(1-piperidinylsulfonyl)benzoate
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC22H22N2O4S
Molar mass410.49 g·mol−1
3D model (JSmol)
  • Cc1ccc(cc1[S](=O)(=O)N2CCCCC2)C(=O)Oc3cccc4cccnc34
  • InChI=1S/C22H22N2O4S/c1-16-10-11-18(15-20(16)29(26,27)24-13-3-2-4-14-24)22(25)28-19-9-5-7-17-8-6-12-23-21(17)19/h5-12,15H,2-4,13-14H2,1H3
  • Key:WORIMYADZQJWOU-UHFFFAOYSA-N

QMPSB is an arylsulfonamide-basedsynthetic cannabinoid that has been sold as adesigner drug.[1]

QMPSB was first discovered by Nathalie Lambeng and colleagues in 2007. It acts as a fullagonist of theCB1 receptor andCB2 receptor with Ki values of 3 nM and 4 nM, respectively.[2] Many related derivatives were subsequently produced, with the main focus of this work being to increase selectivity for the non-psychoactive CB2 receptor.[3][4][5][6] This work led on from an earlier series of sulfamoyl benzamide derivatives for which a patent was filed in 2004.[7]

The quinolin-8-yl estermotif of QMPSB led to the discovery of other designer cannabinoids such asPB-22 andBB-22.[8]

See also

[edit]

References

[edit]
  1. ^Blakey K, Boyd S, Atkinson S, Wolf J, Slottje PM, Goodchild K, McGowan J (March 2016)."Identification of the novel synthetic cannabimimetic 8-quinolinyl 4-methyl-3-(1-piperidinylsulfonyl)benzoate (QMPSB) and other designer drugs in herbal incense".Forensic Science International.260:40–53.doi:10.1016/j.forsciint.2015.12.001.PMID 26795397.
  2. ^Lambeng N, Lebon F, Christophe B, Burton M, De Ryck M, Quéré L (January 2007). "Arylsulfonamides as a new class of cannabinoid CB1 receptor ligands: identification of a lead and initial SAR studies".Bioorganic & Medicinal Chemistry Letters.17 (1):272–7.doi:10.1016/j.bmcl.2006.09.049.PMID 17027269.
  3. ^Ermann M, Riether D, Walker ER, Mushi IF, Jenkins JE, Noya-Marino B, et al. (March 2008). "Arylsulfonamide CB2 receptor agonists: SAR and optimization of CB2 selectivity".Bioorganic & Medicinal Chemistry Letters.18 (5):1725–9.doi:10.1016/j.bmcl.2008.01.042.PMID 18255291.
  4. ^Worm K, Zhou QJ, Saeui CT, Green RC, Cassel JA, Stabley GJ, et al. (May 2008). "Sulfamoyl benzamides as novel CB2 cannabinoid receptor ligands".Bioorganic & Medicinal Chemistry Letters.18 (9):2830–5.doi:10.1016/j.bmcl.2008.04.006.PMID 18430570.
  5. ^Goodman AJ, Ajello CW, Worm K, Le Bourdonnec B, Savolainen MA, O'Hare H, et al. (January 2009). "CB2 selective sulfamoyl benzamides: optimization of the amide functionality".Bioorganic & Medicinal Chemistry Letters.19 (2):309–13.doi:10.1016/j.bmcl.2008.11.091.PMID 19091565.
  6. ^Sellitto I, Le Bourdonnec B, Worm K, Goodman A, Savolainen MA, Chu GH, et al. (January 2010). "Novel sulfamoyl benzamides as selective CB(2) agonists with improved in vitro metabolic stability".Bioorganic & Medicinal Chemistry Letters.20 (1):387–91.doi:10.1016/j.bmcl.2009.10.062.PMID 19919895.
  7. ^US application 7297796, Roland E. Dolle, Karin Worm, Q. Jean Zhou, "Sulfamoyl benzamide derivatives and methods of their use", published Nov 20, 2007, assigned to Adolor Corporation 
  8. ^Brandt SD, Kavanagh PV, Westphal F, Dreiseitel W, Dowling G, Bowden MJ, Williamson JP (2020)."Synthetic cannabinoid receptor agonists: analytical profiles and development of QMPSB, QMMSB, QMPCB, 2F-QMPSB, QMiPSB, and SGT-233".Drug Testing and Analysis.13 (1):175–196.doi:10.1002/dta.2913.PMID 32880103.
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