3574-01-4

Basic information

• Product Name: 1-phenyl-2,3,4,9-tetrahydro-1H-beta-carboline hydrochloride
• Synonyms: 1-phenyl-2,3,4,9-tetrahydro-1H-beta-carboline hydrochloride;1-phenyl-2,3,4,9-tetrahydro-1H-$b-carboline hydrochloride;1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole hydrochloride;1-Phenyltetrahydronorharman hydrochloride;9H-Pyrido(3,4-b)indole, 1,2,3,4-tetrahydro-1-phenyl-, hydrochloride;9H-Pyrido(3,4-b)indole, 1,2,3,4-tetrahydro-1-phenyl-, monohydrochloride
• CAS NO: 3574-01-4
• Molecular Formula: C₁₇H₁₆N₂*ClH
• Molecular Weight: 284.78328
• Mol File: 3574-01-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 254-258 °C(Solv: ethanol (64-17-5))
• Boiling Point: 444.7°Cat760mmHg
• Flash Point: 222.7°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 4.19E-08mmHg at 25°C
• CAS DataBase Reference: 1-phenyl-2,3,4,9-tetrahydro-1H-beta-carboline hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 1-phenyl-2,3,4,9-tetrahydro-1H-beta-carboline hydrochloride(3574-01-4)
• EPA Substance Registry System: 1-phenyl-2,3,4,9-tetrahydro-1H-beta-carboline hydrochloride(3574-01-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 3574-01-4(Hazardous Substances Data)

Usage

Molecular Weight

284.77 g/mol

Chemical Family

Beta-carbolines

Psychoactive Alkaloid

Yes

Potential Neurological Effects

Yes

Derivative of Beta-carboline

Yes

Ability to Bind to Brain Receptors

Yes

Modulation of Neurotransmitter Activity

Yes

Common Salt Form

Hydrochloride

Used in Research and Clinical Studies

Yes

Potential Therapeutic Agent for Neurological Disorders

Yes

Tool for Understanding Central Nervous System

Yes

Starting Point for Development of Novel Drugs

Possible

Further Research Needed

Yes

InChI:InChI=1/C17H16N2.ClH/c1-2-6-12(7-3-1)16-17-14(10-11-18-16)13-8-4-5-9-15(13)19-17;/h1-9,16,18-19H,10-11H2;1H

Upstream product

• 5956-86-5 tryptamine-2-carboxylic acid 
• 100-52-7 benzaldehyde 
• 611-73-4 Benzoylformic acid 
• 61-54-1 tryptamine 
• 4753-09-7 N-benzoyltryptamine 
• 10022-79-4 1-phenyl-4,9-dihydro-3H-β-carboline 
• 343-94-2 tryptamine hydochloride 
• 3790-45-2 1-phenyl-2,3,4,9-tetrahydro-1H-beta-carboline 
• 541-41-3 chloroformic acid ethyl ester 

Downstream Products

• 142696-56-8 (S)-1-phenyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole 
• 148261-76-1 (R)-1-phenyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole 
• 16765-79-0 1-phenyl-9H-pyrido[3,4-b]indole 
• 22294-23-1 2-(2-benzyl-1H-indol-3-yl)ethanamine 
• 3790-45-2 1-phenyl-2,3,4,9-tetrahydro-1H-beta-carboline 

Relevant articles and documents

Asymmetric Biocatalytic Synthesis of 1-Aryltetrahydro-β-carbolines Enabled by “Substrate Walking”

Stereoselective catalysts for the Pictet–Spengler reaction of tryptamines and aldehydes may allow a simple and fast approach to chiral 1-substituted tetrahydro-β-carbolines. Although biocatalysts have previously been employed for the Pictet–Spengler react

Monoamine oxidase (MAO-N) catalyzed deracemization of tetrahydro-β- carbolines: Substrate dependent switch in enantioselectivity

The tetrahydro-β-carboline (THBC) ring system is an important structural motif found in a large number of bioactive alkaloid natural products. Herein we report a broadly applicable method for the synthesis of enantiomerically pure β-carbolines via a deracemization procedure employing the D9 and D11 variants of monoamine oxidase from Aspergillus niger (MAO-N) in combination with a nonselective chemical reducing agent. Biotransformations were performed on a preparative scale, leading to the synthesis of optically enriched products in excellent enantiomeric excess (e.e.; up to 99%) and isolated yield (up to 93%). Interestingly, a switch in enantioselectivity associated with the MAO-N variants is observed as the nature of the C-1 substituent of the THBC is varied. Molecular modeling provided an explanation for this observation and highlighted key active site residues which were modified, resulting in an increase in (R)-selectivity associated with the enzyme. These results provide insight into the factors which influence the selectivity of the MAO-N variants, and may offer a platform for future directed evolution projects aimed toward the challenge of engineering (R)-selective amine oxidase biocatalysts.

Microwave-assisted one-pot preparation of tetrahydro-β-carboline hydrochlorides under solvent-free conditions

An efficient and environmentally friendly synthesis of tetrahydro-β- carboline hydrochlorides via Pictet-Spengler reaction was described. Tryptamine hydrochlorides were used as the reactant and no additional acid catalyst was needed. This reaction was com