304-53-0

Basic information

• Product Name: 1-(INDOL-3-YL)-2-METHYLPROPAN-2-AMINE
• Synonyms: 1-(INDOL-3-YL)-2-METHYLPROPAN-2-AMINE;3-(2-amino-2-methylpropyl)-indol;alpha,alpha-dimethyl-1h-indole-3-ethanamin;alpha,alpha-dimethyltryptamine;2-(1H-INDOL-3-YL)-1,1-DIMETHYL-ETHYLAMINE;1H-Indole-3-ethanamine, alpha,alpha-dimethyl- (9ci);Brn 0127833;Indole, 3-(2-amino-2-methylpropyl)-
• CAS NO: 304-53-0
• Molecular Formula: C₁₂H₁₆N₂
• Molecular Weight: 188.27
• Mol File: 304-53-0.mol

Chemical Properties

• Melting Point: 130-131℃
• Boiling Point: 349°Cat760mmHg
• Flash Point: 191.8°C
• Appearance: /
• Density: 1.098g/cm³
• Vapor Pressure: 4.85E-05mmHg at 25°C
• Refractive Index: 1.628
• Solubility: MeOH, CHCl3, DMSO
• CAS DataBase Reference: 1-(INDOL-3-YL)-2-METHYLPROPAN-2-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(INDOL-3-YL)-2-METHYLPROPAN-2-AMINE(304-53-0)
• EPA Substance Registry System: 1-(INDOL-3-YL)-2-METHYLPROPAN-2-AMINE(304-53-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 304-53-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
1-(INDOL-3-YL)-2-METHYLPROPAN-2-AMINE is used as an intermediate in the synthesis of Bucindolol (B689430), a high-affinity, competitive beta blocker. 1-(INDOL-3-YL)-2-METHYLPROPAN-2-AMINE is utilized in the treatment of congestive heart failure and hypertension, making it a valuable component in the pharmaceutical industry.

InChI:InChI=1/C12H16N2/c1-12(2,13)7-9-8-14-11-6-4-3-5-10(9)11/h3-6,8,14H,7,13H2,1-2H3

Upstream product

• 835-40-5 3-(2,2-dimethyl-2-nitroethyl)-1H-indole 
• 87-52-5 3-(Dimethylaminomethyl)indole 
• 79-46-9 2-nitropropane 
• 7732-18-5 water 
• 120-72-9 indole 

Downstream Products

• 72742-68-8 1-[[2-(3-indolyl)-1,1-dimethylethyl]amino]-3-[2-(methylthio)phenoxy]-2-propanol 
• 77216-35-4 1-(2,6-dimethylphenoxy)-3-[[2-(3-indolyl)-1,1-dimethylethyl]amino]-2-propanol 
• 72742-73-5 1-(4-chloro-2-methylphenoxy)-3-[[2-(3-indolyl)-1,1-dimethylethyl]amino]-2-propanol 
• 72742-64-4 1-(2-fluorophenoxy)-3-[[2-(3-indolyl)-1,1-dimethylethyl]amino]-2-propanol 
• 77216-31-0 1-[[2-(3-indolyl)-1,1-dimethylethyl]amino]-3-[2-(2-propenyl)phenoxy]-2-propanol 
• 72742-63-3 2-[2-hydroxy-3-[[2-(3-indolyl)-1,1-dimethylethyl]amino]propoxy]benzamide 
• 72742-60-0 1-(Biphenyl-2-yloxy)-3-[2-(1H-indol-3-yl)-1,1-dimethyl-ethylamino]-propan-2-ol 
• 77216-36-5 1-(2-cyclohexylphenoxy)-3-[[2-(1H-indol-3-yl)-1,1-dimethylethyl]amino]-2-propanol 
• 1265633-74-6 N-(1-(1H-indol-3-yl)-2-methylpropan-2-yl)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide 
• 77216-05-8 1,1'-[[1,1-dimethyl-2-(1H-indol-3yl)ethyl]imino]bis[3-(2-cyanophenoxy)-2-propanol] 
• 1237817-77-4 [2-(1H-indol-3-yl)-1,1-dimethylethyl]{2-[2-(tetrahydrofur-2-ylmethyloxy)phenoxy]ethyl}amine hydrochloride 

Relevant articles and documents

Spirotetrahydro β-carbolines (spiroindolones): A new class of potent and orally efficacious compounds for the treatment of malaria

The antiplasmodial activity of a series of spirotetrahydro β-carbolines is described. Racemic spiroazepineindole (1) was identified from a phenotypic screen on wild type Plasmodium falciparum with an in vitro IC50 of 90 nM. Structure-activity relationships for the optimization of 1 to compound 20a (IC50 = 0.2 nM) including the identification of the active 1R,3S enantiomer and elimination of metabolic liabilities is presented. Improvement of the pharmacokinetic profile of the series translated to exceptional oral efficacy in the P. berghei infected malaria mouse model where full cure was achieved in four of five mice with three daily doses of 30 mg/kg.

N-ARYLOXYALKYL TRYPTAMINE ALPHA1-ADRENERGIC RECEPTOR ANTAGONISTS

The present invention relates to novel N-aryloxyalkyl tryptamine . alpha. 1-adrenergic receptor antagonists of the formula I: STR1 in which n is 2, 3 or 4; q is 1, 2 or 3; t is 0, 1, 2 or 3; z is 0, 1, 2 or 3; each R 1 and R 2 are independently hydroxy, halogen, cyano, (C 1-8)alkyl, (C 1-8)alkyloxy or trifluoromethyl; and R 2 is hydrogen, (C 1-4)alkyl, fluoro(C 1-4)alkyl, difluoro(C 1-4) alkyl, trifluoro(C 1-4)alkyl, (C 1-4) alkyloxy(C 1-4)alkyl, oxo(C 1-4)alkyl, (C 1-8)cycloalkyl, (C. sub.1-8)cycloalkylmethyl or allyl or phenyl(C 1-4)alkyl or heterocyclo(C 1-8)alkyl (optionally substituted with one to two substituents independently selected from (C 1-4)alkyl, (C 1-4) alkyloxy, trifluoromethyl and halogen); R. sup.3 and R 4 are independently hydrogen, (C 1-4) alkyl, (C 1-8)cycloalkyl, (C 1-8)cycloalkylmethyl or allyl; and R. sup. 5 is hydrogen, (C 1-4)alkyl, (C 1-8)cycloalkyl, (C 1-8) cycloalkylmethyl, allyl, (C 1-4) alkylsulfonyl and aminocarbonyl; with the proviso that when n is 2, t is 0, q is 1, z is 0, 1 or 2, R 5 is hydrogen and R 6 is hydroxy or (C 1-8)alkyloxy then at least one of R 3 and R 4 is not hydrogen; and the pharmaceutically acceptable salts, individual isomers, and mixtures of isomers thereof; their uses as therapeutic agents and the methods of their making.

Antihypertensive indole derivatives of phenoxypropanolamines with β-adrenergic receptor antagonist and vasodilating activity

A series of 25 aryloxypropanolamines containing the 3-indolyl-tert-butyl[i.e., 1,1-dimethyl-2-(1H-indol-3-yl)ethyl] or substituted 3-indolyl-tert-butyl moiety as the N substituent is reported. These compounds have been tested for antihypertensive activity in spontaneously hypertensive rats (SHR), β-adrenergic receptor antagonist action in conscious normotensive rats, vasodilating activity in ganglion-blocked rats with blood pressure maintained by angiotensin II infusion, and for intrinsic sympathomimetic action (ISA) in reserpinized rats. Some of the compounds exhibit antihypertensive activity in combination with β-adrenergic receptor antagonist and vasodilating action. The structure-activity relationships in these tests are discussed.

3-INDOLYL-TERTIARY BUTYLAMINOPROPANOLS

1-Phenoxy-3-(3-indolyl)-tert.-butyl!amino-2-propanols and related 1-aryloxy compounds are antihypertensive agents having vasodilator and adrenergic β-receptor blocking action. Preferred compounds bear an ortho-substituent in the phenoxy group, and most preferably the cyano group.