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apovincamine

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apovincamine Basic information

Product Name:
apovincamine
Synonyms:
  • Methyl (3alpha,16alpha)-eburnamenine-14-carboxylate
  • apovincamine
  • Methyl (13aS,13bS)-13a-ethyl-2,3,5,6,13a,13b-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate
  • methyl (41S,13aS)-13a-ethyl-2,3,41,5,6,13a-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate
  • (3α,16α)-Eburnamenine-14-carboxylic acid methyl ester
  • Apo-14,15-dehydrovincamine
  • Apovincaminic acid methyl
  • (+)-trans-Cavinton
CAS:
4880-92-6
MF:
C21H24N2O2
MW:
336.43
EINECS:
225-491-0
Mol File:
4880-92-6.mol
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apovincamine Chemical Properties

Melting point:
160-162℃
Boiling point:
405.7±45.0 °C(Predicted)
Density 
1.30±0.1 g/cm3(Predicted)
storage temp. 
Refrigerator
solubility 
Chloroform (Slightly), Methanol (Slightly)
pka
7.82±0.60(Predicted)
color 
Off-White to Pale Grey
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Safety Information

HS Code 
2939800000
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apovincamine Usage And Synthesis

Originator

Apovincamine,GC Promochem

Uses

cis-Apovincamine (Vinpocetine USP Related Compound B), is a vinca alkaloid and a chemical precursor of Vinpocetine (V332500), a derivative of Vincamine with vasodilating activity. Vasodilator (cerebral).

Definition

ChEBI: Apovincamine is an alkaloid.

Manufacturing Process

Apovincamine is semisynthethetic derivative of (+)-vincamine. Vincamine is alkaloid of Vinca minor. Alcoloid of Tabernaemontana rigida (Apocynaceae) also is used as raw material for preparing of apovincamine. (+)- Vincamine was transformed into oxime ester by reaction with NaNO2 in acetic acid at 0°C -(+/-)-methyl-3-((12bR)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3- a]quinolizin-1-yl)-2-(hydroxyimino)propanoate, which was resolved on the isomers with dibenzoyl D-tartratic acid. (-)-Methyl 3-((12bR)-1-ethyl- 1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-1-yl)-2- (hydroxyimino)propanoate was re-crystallized from methanol to afford (-)- methyloxime ester, MP: 195°C.
2 g of above oxime methyl ester was heated in mixture of methanol (37.5 ml) and conc. H2SO4 (13.5 ml) on water bath for 1 hour. The solution was poured into ice-water (80 ml), basified with conc. NH4OH to pH 9, and extracted with CH2Cl2 (3x20 ml). The combined extracts were dried (MgSO4), filtered, evaporated in vacuum and the residue was re-crystallized from MeOH (5 ml) to yield 1.32 g (72.5%) of (+)-apovincamine, MP: 160°-162°C.

Therapeutic Function

Vasodilator

apovincamineSupplier

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