QMPSB

QMPSB
Legal status
Legal status	CA: Schedule II;
Identifiers
	IUPAC name 8-quinolinyl 4-methyl-3-(1-piperidinylsulfonyl)benzoate;
CAS Number	312606-87-4;
PubChem CID	3929482;
ChemSpider	3151524;
UNII	55Q8B94HS5;
ChEMBL	ChEMBL245876;
CompTox Dashboard (EPA)	DTXSID901045939 ;
Chemical and physical data
Formula	C22H22N2O4S
Molar mass	410.49 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Cc1ccc(cc1[S](=O)(=O)N2CCCCC2)C(=O)Oc3cccc4cccnc34;
	InChI 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-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 K_i 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.

References

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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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[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] 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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See also

References