63758-79-2 Usage
Description
3-(2-(PIPERIDIN-4-YL)ETHYL)-1H-INDOLE, also known as Indalpine, is a non-tricyclic antidepressant with a selective serotonin profile. It is significantly more potent than fluoxetine and clomipramine in inhibiting serotonin reuptake in vitro in rat brain synaptosomes. Indalpine demonstrates rapid clinical effects, often within one week of treatment onset, and may also provide anxiolytic benefits. 3-(2-(PIPERIDIN-4-YL)ETHYL)-1H-INDOLE is notable for its lack of anticholinergic and cardiovascular side effects, as well as not promoting weight gain or affecting appetite.
Uses
Used in Pharmaceutical Industry:
3-(2-(PIPERIDIN-4-YL)ETHYL)-1H-INDOLE is used as an antidepressant for treating depression due to its high potency in inhibiting serotonin reuptake, leading to increased availability of serotonin in the brain, which contributes to improved mood and reduced symptoms of depression.
Additionally, 3-(2-(PIPERIDIN-4-YL)ETHYL)-1H-INDOLE is used as an anxiolytic for alleviating anxiety symptoms, potentially offering a dual therapeutic effect for patients suffering from both depression and anxiety.
Brand names for 3-(2-(PIPERIDIN-4-YL)ETHYL)-1H-INDOLE include Lm 5008 and UPSTENE.
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 63758-79-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,3,7,5 and 8 respectively; the second part has 2 digits, 7 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 63758-79:
(7*6)+(6*3)+(5*7)+(4*5)+(3*8)+(2*7)+(1*9)=162
162 % 10 = 2
So 63758-79-2 is a valid CAS Registry Number.
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
63758-79-2Relevant articles and documents
Heterocyclic derivatives, their preparation and medicinal products containing them
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, (2008/06/13)
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.