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apovincamine

Product Name
apovincamine
CAS No.
4880-92-6
Chemical Name
apovincamine
Synonyms
Apovincamina;apovincamine;Apovincaminum;Vinpocetine-2;Unii-504R182zx7;Einecs 225-491-0;cis-ApovincaMine;(+)-trans-Cavinton;(+)-trans-Cavinton;Vincamine Impurity D
CBNumber
CB2890058
Molecular Formula
C21H24N2O2
Formula Weight
336.43
MOL File
4880-92-6.mol
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apovincamine Property

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

HS Code 
2939800000
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P330Rinse mouth.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
Y0000591
Product name
Vinpocetine impurity B
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
y0000591
Price
$150
Updated
2024/03/01
Sigma-Aldrich
Product number
1714620
Product name
Vinpocetine impurity B
Packaging
30mg
Price
$1290
Updated
2024/03/01
TRC
Product number
A729245
Product name
cis-Apovincamine
Packaging
10mg
Price
$105
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
PXT0004644
Product name
APOVINCAMINE
Purity
95.00%
Packaging
5MG
Price
$499.54
Updated
2021/12/16
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apovincamine Chemical Properties,Usage,Production

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

apovincamine Preparation Products And Raw materials

Raw materials

Preparation Products

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4880-92-6, apovincamineRelated Search:

Vinpocetine ApovincaMinic Acid Ethyl Ester N-Oxide methyl (41R,12R,13aS)-13a-ethyl-12-hydroxy-2,3,41,5,6,12,13,13a-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate methyl (3alpha,14alpha,16alpha)-14,15-dihydro-14-hydroxyeburnamenine-14-carboxylate (41S,12S,13aS)-13a-ethyl-12-hydroxy-2,3,41,5,6,12,13,13a-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylic acid methyl (41R,12S,13aS)-13a-ethyl-12-hydroxy-2,3,41,5,6,12,13,13a-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate methyl (41S,12S,13aS)-13a-ethyl-12-hydroxy-8-methoxy-2,3,41,5,6,12,13,13a-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate ethyl (41R,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 (+)-(14β)-Dihydrovinpocetine (-)-DihydroapovincaMinic Acid Ethyl Ester ethyl (41S,12R,13aS)-13a-ethyl-12-hydroxy-2,3,41,5,6,12,13,13a-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate ethyl (41S,13aR)-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 methyl (41R,12R,13aR)-13a-ethyl-12-hydroxy-2,3,41,5,6,12,13,13a-octahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate 16,17-Dihydroapovincamine sodium (41S,13aS)-13a-ethyl-2,3,41,5,6,12,13,13a-octahydro- 1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12- carboxylate methyl (41S,12R,13aR)-13a-ethyl-12- hydroxy-2,3,41,5,6,12,13,13aoctahydro- 1H-indolo[3,2,1- de]pyrido[3,2,1-ij][1,5]naphthyridine- 12-carboxylate (3alpha,16alpha)-eburnamenine-14-carboxylic acid ethyl apovincaminate

  • 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
  • Apovincamina
  • Apovincamina [spanish]
  • Apovincaminum
  • Apovincaminum [latin]
  • Eburnamenine-14-carboxylic acid, methyl ester, (3-alpha,16-alpha)-
  • Einecs 225-491-0
  • Methyl (13as,13bs)-13A-ethyl-2,3,4,6,13A,14B-hexahydro-1H-indilol(3.2.1-de)pyrido(3,2,1-ij)(1,5)naphthylridin-12-carboxylat
  • Vincamine EP Impurity B
  • Vinpocetine EP Impurity B
  • 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]phthyridine-12-carboxylate
  • Unii-504R182zx7
  • Vinpocetine Related Compound B (30 mg) (methyl (13aS,13bS)-13a-ethyl-9-methoxy-2,3,5,6,13a,13b-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine-12-carboxylate)
  • IMp. B (EP): 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 (ApovincaMine)
  • Vinpocetine IMp. B (EP)
  • cis-ApovincaMine
  • Vinpocetine Related CoMpound B
  • Vinpocetine-2
  • (41S,13aS)-methyl 13a-ethyl-
  • Methyl (13aS,13bS)-13a-Ethyl-2,3,5,
  • Vinpocetine impurity B CRS
  • Eburnamenine-14-carboxylic acid, methyl ester, (3α,16α)-
  • (+)-trans-Cavinton
  • Vinpocetine Related Compound B(Secondary Standards traceble to USP)
  • Vinpocetine Related Compound B (Methyl(13aS,13bS)-13a-ethyl-2,3,5,6,13a,13b-hexahydro-1H-indolo[3,2 (1714620)
  • Vinpocetine impurity B (apovincamine)
  • Vinpocetine USP Related Compound B
  • methyl14,15-didehydrovincane-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(apovincamine)
  • Vincamine EP Impurity D
  • Vincamine Impurity D
  • (+)-apovincamine, cis-apovincamine
  • 4880-92-6