3382-95-4

Basic information

• Product Name: Vincaminol
• Synonyms: Vincaminol
• CAS NO: 3382-95-4
• Molecular Formula: C20H26N2O2
• Molecular Weight: 326.43264
• Mol File: 3382-95-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 533°C at 760 mmHg
• Flash Point: 276.1°C
• Appearance: /
• Density: 1.37g/cm³
• Vapor Pressure: 3.43E-12mmHg at 25°C
• Refractive Index: 1.704
• CAS DataBase Reference: Vincaminol(CAS DataBase Reference)
• NIST Chemistry Reference: Vincaminol(3382-95-4)
• EPA Substance Registry System: Vincaminol(3382-95-4)

Safety Data

• Hazardous Substances Data: 3382-95-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H26N2O2/c1-2-19-9-5-10-21-11-8-15-14-6-3-4-7-16(14)22(17(15)18(19)21)20(24,12-19)13-23/h3-4,6-7,18,23-24H,2,5,8-13H2,1H3/t18-,19+,20+/m1/s1

Upstream product

• 1617-90-9 vincamin 

Downstream Products

• 65026-49-5 (15S,19S)-15-ethyl-1,11-diazapentacyclo[9.6.2.0^2,7.0^8,18.0^15,19]nonadeca-2,4,6,8⁽¹⁸⁾-tetraene 
• 4880-88-0 vinburnine 

Relevant articles and documents

Preventing Morphine-Seeking Behavior through the Re-Engineering of Vincamine's Biological Activity

Innovative discovery strategies are essential to address the ongoing opioid epidemic in the United States. Misuse of prescription and illegal opioids (e.g., morphine, heroin) has led to major problems with addiction and overdose. We used vincamine, an indole alkaloid, as a synthetic starting point for dramatic structural alterations of its complex, fused ring system to synthesize 80 diverse compounds with intricate molecular architectures. A select series of vincamine-derived compounds were screened for both agonistic and antagonistic activities against a panel of 168 G protein-coupled receptor (GPCR) drug targets. Although vincamine was without an effect, the novel compound 4 (V2a) demonstrated antagonistic activities against hypocretin (orexin) receptor 2. When advanced to animal studies, 4 (V2a) significantly prevented acute morphine-conditioned place preference (CPP) and stress-induced reinstatement of extinguished morphine-CPP in mouse models of opioid reward and relapse. These results demonstrate that the ring distortion of vincamine offers a promising way to explore new chemical space of relevance to opioid addiction.

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.