17403-07-5

Usage

Uses

Used in Pharmaceutical Industry:
3-(1-METHYL-4-PIPERIDINYL)INDOLE is used as a 5-HT6 receptor inhibitor for its potential therapeutic applications in treating various central nervous system disorders. The modulation of the 5-HT6 receptor by 3-(1-METHYL-4-PIPERIDINYL)INDOLE may contribute to the management of cognitive functions and other neurological conditions.
Used in Research and Development:
3-(1-METHYL-4-PIPERIDINYL)INDOLE serves as a valuable research tool in the development of new drugs targeting the 5-HT6 receptor. It can be used to study the receptor's role in physiological and pathological processes, as well as to evaluate the efficacy and safety of new drug candidates.
Used as Naratriptan Impurity:
3-(1-METHYL-4-PIPERIDINYL)INDOLE is also identified as an impurity in Naratriptan (N378730), a drug used for the treatment of migraine. Its presence as an impurity highlights the importance of quality control and purity assessment in pharmaceutical products to ensure their safety and efficacy.

InChI:InChI=1/C14H18N2/c1-16-8-6-11(7-9-16)13-10-15-14-5-3-2-4-12(13)14/h2-5,10-11,15H,6-9H2,1H3

Upstream product

• 13669-28-8 1-methyl-4-methylene-1-azacyclohexane 
• 201230-82-2 carbon monoxide 
• 100-63-0 phenylhydrazine 
• 106-52-5 N-methyl-4-hydroxypiperidine 
• 120-72-9 indole 
• 17403-03-1 3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole 
• 1445-73-4 1-Methyl-4-piperidone 

Relevant academic research and scientific papers

Observations concerning the synthesis of tryptamine homologues and branched tryptamine derivatives via the borrowing hydrogen process: Synthesis of psilocin, bufotenin, and serotonin

Observations concerning the synthesis of substituted tryptamine derivatives starting from indoles and 1,n-amino alcohols via the borrowing hydrogen process are discussed. This catalytic, single-step, and modular approach to tryptamines and homotryptamines allows the synthesis of branched and nonbranched tryptamines as well as tryptamine-based natural products such as psilocin, bufotenin, and serotonin.

PIPERIDINE-INDOLE COMPOUNDS HAVING 5-HT6 AFFINITY

Described herein are indole compounds with affinity for the 5-HT6 receptor, which have general formula (I) wherein, R is selected from the group consisting of H and C1-4alkyl; R is selected from the group consisting of H, C1-4alkyl and benzyl; -----

Synthesis of pharmacologically relevant indoles with amine side chains via tandem hydroformylation/fischer indole synthesis

The sequence of hydroformylation and Fischer indole synthesis starting from amino olefins and aryl hydrazines is described. In a convergent manner, the two units bearing pharmacologically relevant substituents are assembled in the final indolization step. This modular and diversity-oriented approach to tryptamines and homotryptamines can be conducted in water and allows synthesis of branched and nonbranched tryptamines as well as tryptamine-based pharmaceuticals such as the 5-HT1D agonist L 775 606.

Piperidine-indole compounds having 5-HT6 affinity

Described herein are compounds with affinity for the 5-HT6 receptor, which have the general formula: wherein: R1 is selected from the group consisting of H and C1-4alkyl; R2 is selected from the group consisting of H, C1-4alkyl and benzyl; - - - represents a single or double bond; R3 is selected from the group consisting of COR5 and SO2R5; R4a is selected from the group consisting of H, OH, halo, C1-4alkyl and C1-4alkoxy; R4b is selected from the group consisting of H, hydroxy, halo, C3-7cycloalkyloxy, C1-4alkoxy, C1-4alkyl, benzyloxy, phenoxy, trifluoromethyl, trifluoromethoxy and vinyl; R4c is selected from the group consisting of H, OH, halo, C1-4alkyl and C1-4alkoxy; R4d is selected from the group consisting of H, OH, halo, C1-4alkyl and C1-4alkoxy; and R5 is selected from the group consisting of phenyl, pyridyl, thienyl, quinolinyl and naphthyl which are optionally substituted with 1-4 substituents selected from C1-4alkoxy, C1-4alkyl, halo, nitro, trifluoromethyl, trifluoromethoxy, 1,2-methylenedioxy, C1-4alkylcarbonyl, C1-4alkoxycarbonyl and C1-4alkylS-. Also described is the use of these compounds as pharmaceuticals to treat indications where inhibition of the 5-HT6 receptor is implicated, such as schizophrenia.