63758-79-2

Basic information

• Product Name: 3-(2-(PIPERIDIN-4-YL)ETHYL)-1H-INDOLE
• Synonyms: 3-(2-(PIPERIDIN-4-YL)ETHYL)-1H-INDOLE;3-(2-(4-piperidinyl)ethyl)-1h-indol;3-(2-(4-piperidyl)ethyl)-indol;indalpine;lipstene;3-[2-(4-Piperidinyl)ethyl]-1H-indole;LM-5008;Upstene
• CAS NO: 63758-79-2
• Molecular Formula: C₁₅H₂₀N₂
• Molecular Weight: 228.33
• EINECS: 264-445-4
• Mol File: 63758-79-2.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 405.1 °C at 760 mmHg
• Flash Point: 198.8 °C
• Appearance: /
• Density: 1.07 g/cm³
• Vapor Pressure: 9.01E-07mmHg at 25°C
• Refractive Index: 1.595
• CAS DataBase Reference: 3-(2-(PIPERIDIN-4-YL)ETHYL)-1H-INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-(PIPERIDIN-4-YL)ETHYL)-1H-INDOLE(63758-79-2)
• EPA Substance Registry System: 3-(2-(PIPERIDIN-4-YL)ETHYL)-1H-INDOLE(63758-79-2)

Safety Data

• RIDADR: 3249
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 63758-79-2(Hazardous Substances Data)

Usage

Description

Indalpine is a non-tricyclic antidepressant with a serotonin selective profile. It is 6-7 times more potent than fluoxetine and clomipramine in inhibiting serotonin reuptake in vitro in rat brain synaptosomes. Statistically significant clinical effects within one week of onset of treatment have been reported. An anxiolytic effect may accompany the antidepressant effect. Indalpine appears devoid of anticholinergic and cardiovascular side effects and does not promote weight gain or affect appetite.

Manufacturing Process

0.5 g of bis(methoxy-2ethoxy)sodium aluminum hydride in a 70% solution in toluene is added to a solution of 0.29 g of (indolyl-3)(piperidyl-4-methyl) ketone in 10 ml of toluene. The mixture is heated under refluxing conditions for 15 hours, then cooled to 0°C. 10 ml of an aqueous solution of 5N sodium hydroxide is added dropwise thereto, followed by stirring for 1 hour. The organic phase is decanted, washed with water, dried using potassium carbonate and evaporated under partial vacuum. 0.26 g of oil is obtained, which is purified by chromatography and hydrochloride formation. The productobtained is 0.1 g of (indolyl-3)-2-ethyl-4-piperidine hydrochloride which has a melting point of 167°C.

Brand name

Lm 5008;UPSTENE.

Therapeutic Function

Antidepressant

World Health Organization (WHO)

Indalpine, an antidepressant with serotoninergic action, was introduced in 1983 and marketed exclusively in France. In 1984 its use was associated with cases of leucopenia and agranulocytosis which led to the voluntary suspension of clinical trials in the USA. In 1985 the major manufacturer voluntarily withdrew the drug from the market.

InChI:InChI=1/C15H20N2/c1-2-4-15-14(3-1)13(11-17-15)6-5-12-7-9-16-10-8-12/h1-4,11-12,16-17H,5-10H2

Upstream product

• 16571-49-6 3-(2-pyridin-4-yl-ethyl)-indole 
• 120-72-9 indole 
• 100-43-6 4-vinylpyridine 

Relevant articles and documents

Heterocyclic derivatives, their preparation and medicinal products containing them

Compounds are disclosed of formula: in which R1 represents a residue of formula STR1 X represents a hydrogen atom or an alkyl radical, Y represents a hydrogen atom or an alkyl or alkoxy radical, Z represents an alkyl radical, n is equal to 2 or 3, Het represents a substituted piperidino (substituted at the 4-position with a 1-indenylidene, 1-indenyl or 1-indanyl radical or with a chain --(CH2)m --R2 or =CH--R2), substituted 1,2,3,6-tetrahydro-1-pyridyl (substituted at the 4-position with a chain --(CH2)m --R2), m is equal to 1 or 2, and R2 represents an optionally substituted 2- or 3-indolyl radical, a 1- or 2-indanyl, 1- or 2-indenyl, an optionally substituted 1,2,3,4-tetrahydro-5H-pyrido[4,3-b]indol-2-yl radical, a 1,2,3,4-tetrahydro-3-quinolyl radical, an optionally substituted 1,2,3,4-tetrahydro-2-naphthyl radical or a 1-indolyl radical, their preparation and medicinal products containing them.