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

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

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

Downstream Products

• 65020-17-9 (+/-)-N-phthaloyl-1-indol-3-yl-2-aminopropane 
• 7795-51-9 (+)-alpha-Methyltryptamine 
• 7795-52-0 (-)-alpha-Methyltryptamine 
• 120229-28-9 N-[(S)-2-(1H-Indol-3-yl)-1-methyl-ethyl]-butyramide 
• 128632-93-9 {(3R,6S,15S)-3-Benzyl-15-[2-(1H-indol-3-yl)-1-methyl-ethylcarbamoyl]-2,5,9-trioxo-1,4,10-triaza-cyclopentadec-6-yl}-carbamic acid tert-butyl ester 
• 111071-89-7 1-(3,4-Dimethoxyphenyl)-3-methyl-1,2,3,4-tetrahydro-β-carboline 
• 120229-28-9 N-[(R)-2-(1H-Indol-3-yl)-1-methyl-ethyl]-butyramide 
• 668419-17-8 N-[2-(1H-indol-3-yl)-1-methylethyl]-2,4,6-trimethyl-benzenesulfonamide 

Relevant articles and documents

Guanidine-containing compound as well as preparation method and application thereof

The invention discloses a cyanoguanidine-containing compound as well as a preparation method and application thereof. The invention also discloses a composition containing the cyanoguanidine-structured compound (I) or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier. The invention also discloses application thereof in preparation of analgesic drugs. The compounds of the invention are useful in the treatment of various pain.

The base-free van Leusen reaction of cyclic imines on water: Synthesis of N-fused imidazo 6,11-dihydro β-carboline derivatives

Construction of imidazoles has been demonstrated on water under base-free conditions. The reaction of dihydro β-carboline imines and p-toluenesulfonylmethyl isocyanides furnished the corresponding substituted N-fused imidazo 6,11-dihydro β-carboline derivatives in very good yields under ambient conditions. The use of deuterium oxide (D2O) as a solvent enabled the incorporation of deuterium isotopes in the imidazole ring.

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.

INDOLE AHR INHIBITORS AND USES THEREOF

The present invention provides compounds useful as inhibitors of AHR, compositions thereof, and methods of using the same.

BIS-HETEROARYL DERIVATIVES AS MODULATORS OF PROTEIN AGGREGATION

The present invention relates to certain bis-heteroaryl compounds, pharmaceutical compositions containing them, and methods of using them, including methods for preventing, reversing, slowing, or inhibiting protein aggregation, and methods of treating diseases that are associated with protein aggregation, including neurodegenerative diseases such as Parkinson's disease, Alzheimer's disease, Lewy body disease, Parkinson's disease with dementia, fronto- temporal dementia, Huntington's Disease, amyotrophic lateral sclerosis, and multiple system atrophy, and cancer including melanoma.

Asymmetric dearomatization of indoles through a Michael/Friedel-Crafts-Type cascade to construct polycyclic spiroindolines

A highly efficient asymmetric dearomatization of indoles was realized through a cascade reaction between 2-isocyanoethylindole and alkylidene malonates catalyzed by a chiral N,N-dioxide/MgII catalyst. Fused polycyclic indolines containing three stereocenters were afforded in good yields with excellent diastereo- and enantioselectivities through a Michael/Friedel-Crafts/Mannich cascade. When 2-substituted 2-isocyanoethylindoles were used, spiroindoline derivatives were obtained through a Michael/Friedel-Crafts reaction.

Alpha-ethyltryptamines as dual dopamine-serotonin releasers

The dopamine (DA), serotonin (5-HT), and norepinephrine (NE) transporter releasing activity and serotonin-2A (5-HT2A) receptor agonist activity of a series of substituted tryptamines are reported. Three compounds, 7b, (+)-7d and 7f, were found to be potent dual DA/5-HT releasers and were >10-fold less potent as NE releasers. Additionally, these compounds had different activity profiles at the 5-HT2Areceptor. The unique combination of dual DA/5-HT releasing activity and 5-HT2Areceptor activity suggests that these compounds could represent a new class of neurotransmitter releasers with therapeutic potential.

Synthesis and structureactivity relationship of novel conformationally restricted analogues of serotonin as 5-HT6 receptor ligands

5-Hydroxytryptamine 6 receptors (5-HT6R) are being perceived as the possible target for treatment of cognitive disorders as well as obesity. The present article deals with the design, synthesis, in vitro binding and structureactivity relationship of a novel series of tetracyclic tryptamines with the rigidized N-arylsulphonyl, N-arylcarbonyl and N-benzyl substituents as 5-HT6 receptor ligands. The chiral sulphonyl derivatives 15a and 17a showed high affinity at 5-HT6R with the Ki of 23.4 and 20.5nM, respectively. The lead compound from the series 15a has acceptable ADME properties, adequate brain penetration and is active in animal models of cognition like Novel Object Recognition Task (NORT) and water maze.

Straightforward preparation of biologically active 1-aryl- and 1-heteroarylpropan-2-amines in enantioenriched form

Because of the importance of developing stereoselective syntheses for single enantiomers, a selected panel of racemic biologically active 1-aryl- and 1-heteroarylpropan-2-amines has been prepared, followed by a study of their behavior in enzymatic kinetic resolution (KR) processes. For this purpose, lipase B from Candida antarctica (CAL-B) proved to be an ideal biocatalyst allowing the preparation of the corresponding enantioenriched (R)-amides and (S)-amines by aminolysis reactions. Likewise, dynamic kinetic resolutions (DKR) have been successfully achieved combining the use of CAL-B and Shvo's catalyst. This research constitutes the first example of a lipase-catalyzed DKR process of β-substituted isopropylamines.