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;
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 (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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ 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 (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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[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