3851-30-7

Basic information

• Product Name: 1-Benzyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole
• Synonyms: 1-Benzyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole;1-Benzyl-1,2,3,4-tetrahydro-β-carboline;1-Benzyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• CAS NO: 3851-30-7
• Molecular Formula: C₁₈H₁₈N₂
• Molecular Weight: 0
• Mol File: 3851-30-7.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 466.826°C at 760 mmHg
• Flash Point: 236.128°C
• Appearance: /
• Density: 1.205g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.671
• CAS DataBase Reference: 1-Benzyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Benzyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole(3851-30-7)
• EPA Substance Registry System: 1-Benzyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole(3851-30-7)

Safety Data

• Hazardous Substances Data: 3851-30-7(Hazardous Substances Data)

Usage

Chemical class

Tetrahydro beta-carboline

Heterocyclic compound

Yes

Pyrido-indole ring system

Present

Benzyl group attachment

First position

Pharmacological properties

Studied for affinity for serotonin and dopamine receptors

Potential role

Mood and cognition regulation

Potential use

Treatment of neurological disorders and addiction

Research area

Precursor in the synthesis of biologically active compounds in medicinal chemistry

InChI:InChI=1/C18H18N2/c1-2-6-13(7-3-1)12-17-18-14-8-4-5-9-15(14)20-16(18)10-11-19-17/h1-7,9,17,19H,8,10-12H2

Upstream product

• 10022-80-7 1-benzyl-4,9-dihydro-3H-pyrido-[3,4-b]indole 
• 343-94-2 tryptamine hydochloride 
• 122-78-1 phenylacetaldehyde 
• 61-54-1 tryptamine 
• 73955-63-2 2-benzyl-3,4,4-trimethyl-1-(toluene-4-sulfonyl)-imidazolidine 
• 36873-30-0 2-benzyl-4,4,6-trimethyltetrahydro-(2H)-1,3-oxazine 
• 766-04-1 benzyllithium 
• 116965-61-8 2,9-bis-(trimethylsilyl)-3,4-dihydropyrido<3,4-b>indolium trifluoromethane sulphonate 
• 156-06-9 2-oxo-3-(phenyl)propionic acid 
• 100-52-7 benzaldehyde 
• 38879-46-8 (Z)-4-benzylidene-2-methyl-5(4H)-oxazolone 
• 4894-26-2 3,4-dihydro-β-carboline 
• 1589-82-8 phenylmagnesium bromide 
• 103-82-2 phenylacetic acid 

Downstream Products

• 16765-80-3 1-benzyl-β-carboline 
• 913289-12-0 1-benzyl-2-ethyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole 

Relevant articles and documents

Phytochemical meanings of tetrahydro-β-carboline moiety in strictosidine derivatives

Synthesis of 13 different tetrahydro-β-carbolines (THBC) was accomplished by applying the Pictet-Spengler reaction with seven aldehydes, which have been coupled with tryptamine (6) and l-tryptophan methyl ester (7), respectively. The resulting products represent analogues of strictosidine (1) and carboxystrictosidine (5). They were investigated with respect to possible effects on herbivores in feeding bioassays upon the generalist Spodoptera littoralis. Maximum inhibition averages were 42% after four and 46% after six days for the most effective product (19) at 1000 ppm. Additionally, the frass of this particular bioassay was investigated via HPLC-UV for THBC digestion. All synthesized THBCs were also tested for their radical scavenger activity by monitoring their interaction with 2,2-diphenyl-1-picrylhydrazyl (DPPH). Compounds 16-20, 24 and 25 exhibited radical scavenging activity, ranging from 50% to 74% compared to that of α-tocopherol. All results were discussed with respect to possible contributions of tetrahydro-β-carboline moieties in bioactivities of strictosidine (1) and its biodegradation products.

1-Benzyl-1,2,3,4-Tetrahydro-β-Carboline as Channel Blocker of N-Methyl-d-Aspartate Receptors

N-methyl-d-aspartate (NMDA) receptors belong to the family of ligand-gated ion channels and are important for synaptic plasticity and memory function. The NMDA receptor consists of a voltage-dependent channel permeable to Ca2+ and Na+/sup

Reaction of 1-substituted tetrahydro-β-carbolines with activated alkynes - A new original approach to the synthesis of tetrahydroazocino[5,4-b] indoles

The transformations of 1-substituted tetrahydro-β-carbolines by the action of activated alkynes were studied. The action of dimethyl acetylenedicarboxylate in methanol gives products of the opening of the tetrahydropyridine fragment, namely, 2-methoxyalkylindoles. The action of ethyl propiolate in ethanol and of tosylacetylene in methanol gives mixtures of azocino[5,4-b]indoles and 2-alkoxyindoles. The action of ethyl propiolate in acetonitrile gives azocinoindoles.