10252-12-7

Basic information

• Product Name: (12bS)-1,2,3,4,6,7,12,12bβ-Octahydroindolo[2,3-a]quinolizine
• Synonyms: (12bS)-1,2,3,4,6,7,12,12bβ-Octahydroindolo[2,3-a]quinolizine
• CAS NO: 10252-12-7
• Molecular Formula: C15H18N2
• Molecular Weight: 226.31682
• Mol File: 10252-12-7.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (12bS)-1,2,3,4,6,7,12,12bβ-Octahydroindolo[2,3-a]quinolizine(CAS DataBase Reference)
• NIST Chemistry Reference: (12bS)-1,2,3,4,6,7,12,12bβ-Octahydroindolo[2,3-a]quinolizine(10252-12-7)
• EPA Substance Registry System: (12bS)-1,2,3,4,6,7,12,12bβ-Octahydroindolo[2,3-a]quinolizine(10252-12-7)

Safety Data

• Hazardous Substances Data: 10252-12-7(Hazardous Substances Data)

Usage

Description

(12bS)-1,2,3,4,6,7,12,12bβ-Octahydroindolo[2,3-a]quinolizine, also known as rauwolscine, is a chemical compound belonging to the indole alkaloid class. It is found in various plant species, including Rauwolfia serpentina, and is a stereoisomer of yohimbine. Rauwolscine has been studied for its potential medicinal properties, such as its role as an alpha-2 adrenergic receptor antagonist, which may contribute to its use in treating erectile dysfunction, weight loss, and enhancing athletic performance. Its structure and pharmacological activities have made it a subject of interest in drug development and medicinal research.

Uses

Used in Pharmaceutical Industry:
Rauwolscine is used as a potential treatment for erectile dysfunction due to its alpha-2 adrenergic receptor antagonist properties, which may help improve blood flow and erectile function.
Used in Dietary Supplements:
Rauwolscine is used as a dietary supplement for weight loss and athletic performance enhancement. Its alpha-2 adrenergic receptor antagonist activity may contribute to increased metabolism and energy expenditure, promoting weight loss and improved physical performance.
Used in Drug Development and Medicinal Research:
Rauwolscine's structure and pharmacological activities make it a subject of interest in drug development and medicinal research. Its potential applications in treating various conditions, such as erectile dysfunction, weight loss, and athletic performance enhancement, warrant further investigation and development of new therapeutic agents.

Upstream product

• 4942-85-2 1,2,3,4,6,7,12,12b-octahydroindolo<2,3-a>quinolizine-4-one 
• 1444254-58-3 tert-butyl (1S,12bR)-1-acetoxy-4-oxo-1,3, 4 ,6,7,12bhexahydroindolo[2,3-a]quinolizine-12(2H)-carboxylate 
• 1444254-50-5 tert-butyl (S)-3-(2-(3-acetoxy-2,6-dioxopiperidin-1-yl)ethyl)-1H-indole-1-carboxylate 
• 1444254-46-9 tert-butyl (S)-3-(2-(3-hydroxy-2,6-dioxopiperidin-1-yl)ethyl)-1H-indole-1-carboxylate 
• 21461-84-7 (2S)-tetrahydro-5-oxofuran-2-carboxylic acid 
• 167015-84-1 3-(2-aminoethyl)-indole-1-carboxylic acid tert-butyl ester 
• 1444254-42-5 tert-butyl (S)-3-(2-(5-oxotetrahydrofuran-2-carboxamido)ethyl)-1H-indole-1-carboxylate 
• 1444254-70-9 (1S,12bR)-4-oxo-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]-quinolizin-1-yl phenyl carbonate 
• 1444254-66-3 (-)-(1S,12bR)-1-hydroxy-2,3,6,7,12,12b-hexahydroindolo[2,3-a]quinolizin-4(1H)-one 
• 6067-48-7 1,2,3,4,6,7-Hexahydro-12H-indolo<2.3-a>chinolizinium-chlorid 
• 99545-57-0 (1S)-(+)-2--1-(4-chlorobutyl)-9-methoxymethyl-1,2,3,4-tetrahydro-β-carboline 
• 137119-61-0 (+)-(1R,12bR,SR)-1-<(4-methylphenyl)sulfinyl>-1,2,3,4,6,7,12,12b-octahydro-4-oxoindolo<2,3-a>quinolizine 
• 123642-80-8 (+)-(R)-3,4-dihydro-1-<<(4-methylphenyl)sulfinyl>methyl>-β-carboline 
• 525-41-7 1-methyl-4,9-dihydro-3H-β-carboline 

Relevant articles and documents

Highly stereoselective synthesis of the indolo[2,3-a]quinolizine ring system and application to indole natural product synthesis

We report a novel, facile and highly stereoselective approach to the indolo[2,3-a]quinolizine ring system from a readily available, non-racemic chiral template. We demonstrate the potential for application of this methodology to natural product synthesis through conversion of the template to a simple indole alkaloid with high enantiomeric purity.

Enantioselective synthesis of some tetrahydroisoquinoline and tetrahydro-β-carboline alkaloids

Four alkaloids: (R)-(+)-cryspine A 5, (R)-(+)-octahydroindolo[2,3-a]quinolizidine 8, (R)-(+)-harmicine 19 and (R)-(+)-desbromoarborescidine 22 were prepared via the asymmetric transfer hydrogenation reaction of a prochiral enamine (iminium salt). The enan

Enantioselective total synthesis of desbromoarborescidines A-C and the formal synthesis of (S)-deplancheine

Starting from Boc-protected tryptamine and (S)-tetrahydro-5-oxo-2- furancarboxylic acid, facile enantioselective total synthesis of desbromoarborescidines A-C and the formal synthesis of (S)-deplancheine have been accomplished via a common intermediate (S

A highly stereoselective synthesis of the indolo[2,3-a]quinolizine ring system and application to natural product synthesis

We present a facile and highly stereoselective approach to the indolo[2,3-a]quinolizine ring system from a readily available, non-racemic chiral template. We demonstrate the potential for application of this methodology to natural product synthesis throug