16765-80-3

Basic information

• Product Name: 1-benzyl-β-carboline
• Synonyms: 1-benzyl-β-carboline
• CAS NO: 16765-80-3
• Molecular Weight: 258.323
• Mol File: 16765-80-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-benzyl-β-carboline(CAS DataBase Reference)
• NIST Chemistry Reference: 1-benzyl-β-carboline(16765-80-3)
• EPA Substance Registry System: 1-benzyl-β-carboline(16765-80-3)

Safety Data

• Hazardous Substances Data: 16765-80-3(Hazardous Substances Data)

Usage

Chemical class

Carboline

Derivative of

β-carboline

Structure

Benzyl group attached to the nitrogen atom

Potential biological activities

Anti-inflammatory, anti-cancer

Investigated for

Modulating neurotransmitter functions

Preclinical studies

Shown promising results for therapeutic applications

Studied for

Potential as a psychoactive compound

Affinity

For certain neurotransmitter receptors in the brain

Compound of interest

Pharmaceutical and psychoactive properties

Further research needed

To understand mechanisms of action and potential applications

Upstream product

• 3851-30-7 1-benzyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 
• 122-78-1 phenylacetaldehyde 
• 54-12-6 Trp 
• 103-80-0 phenylacetyl chloride 
• 61-54-1 tryptamine 
• 859805-53-1 1-benzyl-3,4-dihydro-β-carboline hydrochloride 
• 19462-24-9 N-phenylacetyltryptamine 
• 103-82-2 phenylacetic acid 

Relevant articles and documents

Synthesis of 1-indolyl substituted β-carboline natural products and discovery of antimalarial and cytotoxic activities

A series of 1-indolyl substituted β-carbolines including the natural products hyrtiosulawesine, pityriacitrin and pityriacitrin B were prepared via Pictet-Spengler condensation - oxidation strategy from the corresponding indolyl-acetaldehydes and substituted tryptamines. Efforts to prepare the C-1 methylene-linked β-carboline analogues for structure-activity relationship studies were unsuccessful. Biological evaluation revealed two analogues (5 and 41) to exhibit weak inhibition of phospholipase A2 (IC50 171 and 131 μM, respectively), two to act as antioxidants (3 and 43), and 12 analogues with activity towards a chloroquine-resistant strain (FcB1) of Plasmodium falciparum (IC50 1.0-23 μM). Testing against a panel of 60 human tumour cell lines revealed a general lack of cytotoxic effect for most of the compounds with the exception of β-carboline 42 exhibiting modest antileukaemic activity towards the HL-60(TB) cell line (LC50 4.2 μM). In addition, two novel structures (30 and 32) resulting from aldol condensation followed by Pictet-Spengler cyclisation displayed cytotoxicity with pronounced subpanel specificities towards colon cancer (COLO 205 and HCC-2998) cell lines.