QMPSB

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QMPSB
QMPSB structure.svg
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC22H22N2O4S
Molar mass410.49 g·mol−1
3D model (JSmol)

QMPSB is an arylsulfonamide-based synthetic cannabinoid that has been sold as a designer drug.[1]

QMPSB was first discovered by Lambeng and colleagues in 2007. It acts as a full agonist of the CB1 receptor and CB2 receptor with Ki values of 3 nM and 4 nM, respectively.[2] A large number of 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 ester motif of QMPSB led to the discovery of other designer cannabinoids such as PB-22 and BB-22.

See also[edit]

References[edit]

  1. ^ Karen Blakey; Sue Boyd; Sarah Atkinson; Jenna Wolf; Pim M. Slottje; Katrina Goodchild; Jenny McGowan (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. ^ N. Lambeng; F. Lebon; B. Christophe; M. Burton; M. De Ryck; L. Quéré (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): 272–277. doi:10.1016/j.bmcl.2006.09.049. PMID 17027269.
  3. ^ Monika Ermann; Doris Riether; Edward R. Walker; Innocent F. Mushi; James E. Jenkins; Beatriz Noya-Marino; Mark L. Brewer; Malcolm G. Taylor; Patricia Amouzegh; Stephen P. East; Brian W. Dymock; Mark J. Gemkow; Andreas F. Kahrs; Andreas Ebneth; Sabine Löbbe; Kathy O’Shea; Daw-Tsun Shih; David Thomson (March 2008). "Arylsulfonamide CB2 receptor agonists: SAR and optimization of CB2 selectivity". Bioorganic & Medicinal Chemistry Letters. 18 (5): 1725–1729. doi:10.1016/j.bmcl.2008.01.042. PMID 18255291.
  4. ^ Karin Worm; Q. Jean Zhou; Christopher T. Saeui; Rosalyn C. Green; Joel A. Cassel; Gabriel J. Stabley; Robert N. DeHaven; Nathalie Conway-James; Christopher J. LaBuda; Michael Koblish; Patrick J. Little; Roland E. Dolle (May 2008). "Sulfamoyl benzamides as novel CB2 cannabinoid receptor ligands". Bioorganic & Medicinal Chemistry Letters. 18 (9): 2830–2835. doi:10.1016/j.bmcl.2008.04.006. PMID 18430570.
  5. ^ Allan J. Goodman; Christopher W. Ajello; Karin Worm; Bertrand Le Bourdonnec; Markku A. Savolainen; Heather O’Hare; Joel A. Cassel; Gabriel J. Stabley; Robert N. DeHaven; Christopher J. LaBuda; Michael Koblish; Patrick J. Little; Bernice L. Brogdon; Steven A. Smith; Roland E. Dolle (January 2009). "CB2 selective sulfamoyl benzamides: Optimization of the amide functionality". Bioorganic & Medicinal Chemistry Letters. 19 (2): 309–313. doi:10.1016/j.bmcl.2008.11.091. PMID 19091565.
  6. ^ Ian Sellitto; Bertrand Le Bourdonnec; Karin Worm; Allan Goodman; Markku A. Savolainen; Guo-Hua Chu; Christopher W. Ajello; Christopher T. Saeui; Lara K. Leister; Joel A. Cassel; Robert N. DeHaven; Christopher J. LaBuda; Michael Koblish; Patrick J. Little; Bernice L. Brogdonc; Steven A. Smithc; Roland E. Dolle (January 2010). "Novel sulfamoyl benzamides as selective CB2 agonists with improved in vitro metabolic stability". Bioorganic & Medicinal Chemistry Letters. 20 (1): 387–391. doi:10.1016/j.bmcl.2009.10.062. PMID 19919895.
  7. ^ ‹See Tfd›US application 7297796, ‹See Tfd›Roland E. Dolle, Karin Worm, Q. Jean Zhou, "Sulfamoyl benzamide derivatives and methods of their use", published Nov 20, 2007, assigned to Adolor Corporation