QMPSB

QMPSB
Legal status
Legal status	CA: Schedule II ; DE: NpSG (Industrial and scientific use only) ; UK: Under Psychoactive Substances Act ;
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;
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] 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 ester motif of QMPSB led to the discovery of other designer cannabinoids such as PB-22 and BB-22.[8]

References

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.
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.
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.
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.
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.
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.
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
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. doi:10.1002/dta.2913.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[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. doi:10.1002/dta.2913.

QMPSB

See also

References