QMPSB

QMPSB
Systematic (IUPAC) name
8-quinolinyl 4-methyl-3-(1-piperidinylsulfonyl)benzoate
Clinical data
Legal status
Identifiers
CAS Number 312606-87-4
PubChem CID 3929482
ChemSpider 3151524
UNII 55Q8B94HS5 YesY
Chemical data
Formula C22H22N2O4S
Molar mass 410.49 g·mol−1

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

References

  1. ↑ Karen Blakey, Sue Boyd, Sarah Atkinson, Jenna Wolf, Pim M. Slottje, Katrina Goodchild, Jenny McGowan (December 2015). "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. doi:10.1016/j.forsciint.2015.12.001.
  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. ↑ 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


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