32790-09-3

Basic information

• Product Name: 17,18-Didehydrovincamine
• Synonyms: (3α,14S,16α)-14,15-Dihydro-17,18-didehydro-14-hydroxyeburnamenine-14-carboxylic acid methyl ester;(3α,14S,16α)-17,18-Didehydro-14,15-dihydro-14β-hydroxyeburnamenine-14-carboxylic acid methyl ester;(3α,16α)-14,15-Dihydro-17,18-didehydro-14-hydroxyeburnamenine-14α-carboxylic acid methyl ester;14,15-Dehydrovincamine;17,18-Didehydrovincamine;Δ14-Vincamine
• CAS NO: 32790-09-3
• Molecular Formula: C₂₁H₂₄N₂O₃
• Molecular Weight: 352.42686
• Mol File: 32790-09-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 224-225 °C
• Boiling Point: 508.7±50.0 °C(Predicted)
• Appearance: /
• Density: 1.35±0.1 g/cm3(Predicted)
• PKA: 12.20±0.40(Predicted)
• CAS DataBase Reference: 17,18-Didehydrovincamine(CAS DataBase Reference)
• NIST Chemistry Reference: 17,18-Didehydrovincamine(32790-09-3)
• EPA Substance Registry System: 17,18-Didehydrovincamine(32790-09-3)

Safety Data

• Hazardous Substances Data: 32790-09-3(Hazardous Substances Data)

Usage

Description

17,18-Didehydrovincamine is a naturally occurring alkaloid compound found as an impurity in Vincamine (V314030). It is structurally similar to Vincamine and has been studied for its potential nootropic and vasodilatory properties.

Uses

Used in Pharmaceutical Industry:
17,18-Didehydrovincamine is used as a nootropic agent for combating the effects of aging. It is often used in conjunction with other nootropics, such as piracetam, to enhance cognitive function and memory.
Used in Neurological Applications:
17,18-Didehydrovincamine is used as a peripheral vasodilator to increase blood flow to the brain. This improved blood flow can help support brain health and function, making it a potential candidate for the treatment of various neurological disorders.
Used in Research and Development:
Due to its structural similarity to Vincamine, 17,18-Didehydrovincamine is also used in research and development to study its potential therapeutic effects and to develop new drugs with improved efficacy and safety profiles.

Upstream product

• 112924-07-9 C₂₁H₂₅N₃O₃ 
• 112817-47-7 (5aR,10aS,11R,12aR,12bS)-5a-Amino-12a-ethyl-11-hydroxy-4,5,5a,10,11,12,12a,12b-octahydro-3H-3a,10-diaza-indeno[1,7-ma]fluorene-11-carboxylic acid methyl ester 
• 4429-63-4 tabersonine 

Downstream Products

• 55872-13-4 criocerine 
• 1617-90-9 vincamin 

Relevant articles and documents

Synthesis of vinca alakaloids and realated compounds 98 [1]. Oxidation with dimethyldioxirane of compounds containing the aspidospermane and quebrachamine ring system. A simple synthesis of (7s,20S)-(+)-rhazidigenine and (2R,7S,20S)-(+)-rhazidine

The oxidation of (-)-tabersonine (1) with dimethyldioxirane (DMD) in neutral and acidic medium gave 16-hydroxytabersonine-N-oxide (3) and the didehydrovincamine isomers 4 and 5, respectively. (+)-14,15-Didehydro-quebrachamine (7) furnished the hydroxyindolenine 9, and the pentacyclic derivative 11. (+)- Quebrachamine (8) and DMD in neutral medium gave (7S,20S)-(+)-rhazidigenine (12) which was converted to (2R,7S,20S)-(+)-rhazidine (13b) with hydrochloric acid.

Synthesis of 18-hydroxyvincamines and epoxy-1,14-secovincamines; A new proof for the aspidospermane-eburnane rearrangement

Chemical transformations started from tabersonine were studied. A one-pot oxidative ring-transformation with permaleic acid in methanol yielded 17,18-dehydrovincamine. Hydroboration-oxidation of the latter compound led to alkaloid 17,18-dehydrovincamone. Hydroboration-oxidation of tabersonine resulted 14β-hydroxyvincadifformine and 15β-hydroxyvincadifformine. Allowing 14β- and 15β- hydroxyvincadifformines to react with permaleic acid/methanol provided 1,14-secovincamines, serving as new evidence for the mechanism of the aspidospermane-eburnane transformation. On the other hand 18β-hydroxyvincamine was obtained from 14β-hydroxyvincadifformine by reaction with 3-chloroperbenzoic acid and successive treatment with triphenylphosphine/aqueous acetic acid.

Ozonation in Alkaloid Chemistry: a Mild and Selective Conversion of Vincadifformine into Vincamine

Vincamine has been obtained in a 'one-pot' method by ozonation of vincadifformine.