299-26-3

Basic information

• Product Name: 3-(2-AMINOPROPYL)INDOLE
• Synonyms: 1-(1H-Indol-3-yl)-2-propanamine;164 E;1H-Indole-3-ethanamine, alpha-methyl-;3-(2-aminopropyl)-indol;alpha-Methyl-3-indoleethanamine;AMT(α-MethyltryptaMine);1-(1H-Indol-3-yl)propan-2-amine 2-(1H-Indol-3-yl)-1-methyl-ethylamine;alpha-methyl-beta-indolaethylamine
• CAS NO: 299-26-3
• Molecular Formula: C11H14N2
• Molecular Weight: 174.24
• EINECS: 206-073-7
• Product Categories: Tryptamines
• Mol File: 299-26-3.mol
• Article Data: 15

Chemical Properties

• Melting Point: 97-101 °C
• Boiling Point: 295.23°C (rough estimate)
• Flash Point: 189 °C
• Appearance: white to slightly yellow crystals or cryst. powder
• Density: 0.9649 (rough estimate)
• Vapor Pressure: 6.55E-05mmHg at 25°C
• Refractive Index: 1.6210 (estimate)
• Storage Temp.: Poison room
• PKA: 17.22±0.30(Predicted)
• CAS DataBase Reference: 3-(2-AMINOPROPYL)INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2-AMINOPROPYL)INDOLE(299-26-3)
• EPA Substance Registry System: 3-(2-AMINOPROPYL)INDOLE(299-26-3)

Safety Data

• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 24/25-45-36/37/39-26-22
• RIDADR: 2811
• RTECS: NL4550000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 299-26-3(Hazardous Substances Data)

Usage

Definition

ChEBI: A tryptamine derivative having a methyl substituent at the alpha-position.

Safety Profile

Poison by ingestion and intraperitoneal routes. Moderately toxic by subcutaneous route. Human psychotropic effects by ingestion. An experimental teratogen. Other experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx,.

InChI:InChI=1/C11H14N2/c1-8(12)6-9-7-13-11-5-3-2-4-10(9)11/h2-5,7-8,13H,6,12H2,1H3/p+1/t8-/m1/s1

Upstream product

• 1201-26-9 3-(1H-indolyl)acetone 
• 487-89-8 Indole-3-carboxaldehyde 
• 4771-72-6 α-methyl-β-(3-indolyl)-1-nitroethane 
• 64252-02-4 3-(β-nitro-β-methylvinyl)indole 
• 120-72-9 indole 
• 22693-51-2 3-(2-nitroprop-1-en-1-yl)-1H-indole 

Downstream Products

• 7795-52-0 (-)-alpha-Methyltryptamine 
• 120229-28-9 N-[(S)-2-(1H-Indol-3-yl)-1-methyl-ethyl]-butyramide 
• 120229-28-9 N-[(R)-2-(1H-Indol-3-yl)-1-methyl-ethyl]-butyramide 
• 695805-38-0 [2-(1H-indol-3-yl)-1-methyl-ethyl]-carbamic acid phenyl ester 
• 1100754-12-8 N-(((S)-1-(1H-indol-3-yl)propan-2-ylcarbamoyl)methyl)octanamide 
• 870102-03-7 2-[4-dimethylamino-4-(4-fluoro-phenyl)-cyclohexylidene]-N-[2-(1H-indol-3-yl)-1-methyl-ethyl]-acetamide 
• 870102-05-9 2-[4-dimethylamino-4-(3-fluoro-phenyl)-cyclohexylidene]-N-[2-(1H-indol-3-yl)-1-methyl-ethyl]-acetamide 
• 128600-64-6 2-[2-(1-Benzyl-1H-indol-3-yl)-1-methyl-ethyl]-isoindole-1,3-dione 
• 48184-03-8 (+/-)-1-(1-benzylindol-3-yl)-2-aminopropane 
• 106288-11-3 3-[1-(3,4-Dimethoxy-phenyl)-3-methyl-1,3,4,9-tetrahydro-β-carbolin-2-yl]-1-morpholin-4-yl-propan-1-one 
• 106288-07-7 2-[1-(3,4-Dimethoxy-phenyl)-3-methyl-1,3,4,9-tetrahydro-β-carbolin-2-yl]-1-morpholin-4-yl-ethanone 
• 106288-10-2 3-[1-(3,4-Dimethoxy-phenyl)-3-methyl-1,3,4,9-tetrahydro-β-carbolin-2-yl]-N,N-dipropyl-propionamide 
• 106314-74-3 1-(3,4-Dimethoxy-phenyl)-3-methyl-2-(3-morpholin-4-yl-propyl)-2,3,4,9-tetrahydro-1H-β-carboline 
• 106288-06-6 2-[1-(3,4-Dimethoxy-phenyl)-3-methyl-1,3,4,9-tetrahydro-β-carbolin-2-yl]-N,N-dipropyl-acetamide 

Relevant articles and documents

Indole derivatives. XLIV. Preparative synthesis of indopan from indole

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Virtual screening-driven discovery of dual 5-HT6/5-HT2A receptor ligands with pro-cognitive properties

A virtual screening campaign aimed at finding structurally new compounds active at 5-HT6R provided a set of candidates. Among those, one structure, 4-(5-{[(2-{5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl}ethyl)amino]methyl}furan-2-yl)phenol (1, 5-HT6R Ki = 91 nM), was selected as a hit for further optimization. As expected, the chemical scaffold of selected compound was significantly different from all the serotonin receptor ligands published to date. Synthetic efforts, supported by molecular modelling, provided 43 compounds representing different substitution patterns. The derivative 42, 4-(5-{[(2-{5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl}ethyl)amino]methyl}furan-2-yl)phenol (5-HT6R Ki = 25, 5-HT2AR Ki = 32 nM), was selected as a lead and showed a good brain/plasma concentration profile, and it reversed phencyclidine-induced memory impairment. Considering the unique activity profile, the obtained series might be a good starting point for the development of a novel antipsychotic or antidepressant with pro-cognitive properties.

A Br?nsted Acid Catalyzed Cascade Reaction for the Conversion of Indoles to α-(3-Indolyl) Ketones by Using 2-Benzyloxy Aldehydes

A Br?nsted acid catalyzed, operationally simple, scalable route to several functionalized α-(3-indolyl) ketones has been developed and the long-standing regioisomeric issue has been eliminated by choosing appropriate carbonyls. A readily available and cheap bottle reagent was used as the catalyst. This protocol was also applicable to the synthesis of densely functionalized α-(3-pyrrolyl) ketones. A detailed mechanistic study confirmed the involvement of enolether as a reaction intermediate. Several postsynthetic modifications along with easy access to β-carboline, tryptamines, tryptophols, and spiro-indolenine proclaim the synthetic utility of this powerful building block. On the basis of this concept, functionalized carbazoles were constructed by a cascade annulation strategy.