263384-65-2

Basic information

• Product Name: MS 245 oxalate
• Synonyms: MS 245 oxalate;MS 245;2-(5-Methoxy-1-(phenylsulfonyl)-1H-indol-3-yl)-N,N-dimethylethanamine oxalate;2-[1-(benzenesulfonyl)-5-methoxyindol-3-yl]-N,N-dimethylethanamine
• CAS NO: 263384-65-2
• Molecular Formula: C₁₉H₂₂N₂O₃S
• Molecular Weight: 448.5
• Mol File: 263384-65-2.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: MS 245 oxalate(CAS DataBase Reference)
• NIST Chemistry Reference: MS 245 oxalate(263384-65-2)
• EPA Substance Registry System: MS 245 oxalate(263384-65-2)

Safety Data

• Hazardous Substances Data: 263384-65-2(Hazardous Substances Data)

Usage

Description

MS 245 oxalate is a 5-HT6 antagonist with high affinity, which is a type of drug that blocks the action of serotonin at the 5-HT6 receptor. It is known for its ability to increase the hypolocomotor actions of (-)-nicotine in mice.

Uses

Used in Pharmaceutical Industry:
MS 245 oxalate is used as a 5-HT6 antagonist for its potential therapeutic effects in treating various neurological and psychiatric disorders. Its ability to block the 5-HT6 receptor may help in modulating serotonin signaling pathways, which could be beneficial in managing conditions such as Alzheimer's disease, schizophrenia, and depression.
Used in Research Applications:
MS 245 oxalate is used as a research tool for studying the role of the 5-HT6 receptor in various biological processes and its potential as a target for drug development. Its high affinity for the 5-HT6 receptor makes it a valuable compound for investigating the mechanisms of action and potential therapeutic applications of 5-HT6 antagonists.
Used in Nicotine Research:
MS 245 oxalate is used in nicotine research for its ability to increase the hypolocomotor actions of (-)-nicotine in mice. This property makes it a useful compound for studying the effects of nicotine on locomotor activity and potentially developing treatments for nicotine addiction or other nicotine-related conditions.

Upstream product

• 1019-45-0 N,N-dimethyl-5-methoxytryptamine 
• 98-09-9 benzenesulfonyl chloride 

Downstream Products

• 263384-66-3 1-benzenesulfonyl-3-(dimethylaminoethyl)-2-n-propyl-5-methoxyindole 

Relevant articles and documents

N1-(Benzenesulfonyl)tryptamines as novel 5-HT6 antagonists.

N-Benzenesulfonyl-5-methoxy-N,N-dimethyltryptamine (BS/5-OMe DMT; 5) was shown to bind at human 5-HT6 serotonin receptors with high affinity (Ki = 2.3 nM) relative to serotonin (Ki = 78 nM). Structural variation failed to result in significantly enhanced affinity. BS/5-OMe DMT acts as an antagonist of 5-HT-stimulated adenylate cyclase (pA2 = 8.88 nM) and may represent the first member of a novel class of 5-HT6 antagonists.

N-arylsulfonylindole derivatives as serotonin 5-HT6 receptor ligands

A series of N1-arylsulfonyltryptamines were found to be potent ligands of the human serotonin 5-HT6 receptor with the 5-methoxy-1-benzenesulfonyl analogue (19) having the highest affinity. Additionally, it was discovered that a group such as 3-(3-methoxybenzyl)-1,2,4-oxadiazol-5-yl in the 2-position of the indole ring (43) can replace the arylsulfonyl substituent in the 1-position with no loss of affinity. This suggested that the binding conformation of the aminoethyl side chain at this receptor was toward the 4-position of the indole ring and was supported by the fact that the 4-(aminoethyl)indoles (45) also displayed high affinity, as did the conformationally rigid 1,3,4,5-tetrahydrobenz[c,d]indole (49). Molecular modeling showed that 19, 43, and 45 all had low-energy conformers that overlaid well onto 49. Both 19 and 49 had good selectivity over other serotonin receptors tested, with 49 also showing excellent selectivity over all dopamine receptors. In a functional adenylate cyclase stimulation assay, 19 and 49 had no agonist activity, whereas 45 behaved as a partial agonist. Finally, it was shown that 19 had good activity in the 5-HT2A centrally mediated mescaline-induced head twitch assay, which implies that it is brain-penetrant.

2-Substituted tryptamines: Agents with selectivity for 5-HT6 serotonin receptors

Several 2-alkyl-5-methoxytryptamine analogues were designed and prepared as potential 5-HT6 serotonin agonists. It was found that 5-HT6 receptors accommodate small alkyl substituents at the indole 2-position and that the resulting co