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MS-245
Systematic (IUPAC) name
2-[5-methoxy-1-(phenylsulfonyl)-1H-indol-3-yl]- N,N-dimethylethanamine
Identifiers
CAS number  ?
ATC code  ?
PubChem 6918542
Chemical data
Formula C 19H22N2O3S 
Mol. mass 358.454 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes  ?

MS-245 is a tryptamine derivative which is used in scientific research. It acts as a selective 5-HT6 receptor antagonist with a Ki of 2.3nM, and was derived through structure-activity relationship development of the selective 5-HT6 agonist EMDT.[1] It has been used as a lead compound for further development of tryptamine-derived 5-HT6 antagonists.[2][3] In animal studies it has been shown to boost the activity of, but not to substitute for, both amphetamine and nicotine.[4][5]

For tetrahydrocarbazole constrained analogs it was shown that the amino function is not required for receptor binding.[6]

For pyrrolidinylmethylindole analogs the higher affinity resides in the R-enantiomere (Ki of 5d = 0.3nM).[7]

References

  1. ^ Tsai Y, Dukat M, Slassi A, MacLean N, Demchyshyn L, Savage JE, Roth BL, Hufesein S, Lee M, Glennon RA. N1-(Benzenesulfonyl)tryptamines as novel 5-HT6 antagonists. Bioorganic and Medicinal Chemistry Letters. 2000 Oct 16;10(20):2295-9. PMID 11055342
  2. ^ Abate C, Kolanos R, Dukat M, Setola V, Roth BL, Glennon RA. Interaction of chiral MS-245 analogs at h5-HT6 receptors. Bioorganic and Medicinal Chemistry Letters. 2005 Aug 1;15(15):3510-3. PMID 15990303
  3. ^ Dukat M, Mosier PD, Kolanos R, Roth BL, Glennon RA. Binding of serotonin and N1-benzenesulfonyltryptamine-related analogs at human 5-HT6 serotonin receptors: receptor modeling studies. Journal of Medicinal Chemistry. 2008 Feb 14;51(3):603-11. PMID 18201064
  4. ^ Pullagurla M, Bondareva T, Young R, Glennon RA. Modulation of the stimulus effects of (+)amphetamine by the 5-HT6 antagonist MS-245. Pharmacology, Biochemistry and Behaviour. 2004 Jun;78(2):263-8. PMID 15219766
  5. ^ Young R, Bondareva T, Wesolowska A, Young S, Glennon RA. Effect of the 5-HT(6) serotonin antagonist MS-245 on the actions of (-)nicotine. Pharmacology, Biochemistry and Behaviour. 2006 Sep;85(1):170-7. PMID 16950502
  6. ^ Chang-Fong J, Rangisetty JB, Dukat M, et al. (April 2004). "1,2,3,4-tetrahydrocarbazoles as 5-HT6 serotonin receptor ligands". Bioorg. Med. Chem. Lett. 14 (8): 1961–4. doi:10.1016/j.bmcl.2004.01.071. PMID 15050637.  
  7. ^ Abate C, Kolanos R, Dukat M, Setola V, Roth BL, Glennon RA (August 2005). "Interaction of chiral MS-245 analogs at h5-HT6 receptors". Bioorg. Med. Chem. Lett. 15 (15): 3510–3. doi:10.1016/j.bmcl.2005.05.092. PMID 15990303.  
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