apovincamine
Synonym(s):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;Vinpocetine EP Impurity B
- CAS NO.:4880-92-6
- Empirical Formula: C21H24N2O2
- Molecular Weight: 336.43
- MDL number: MFCD00867558
- EINECS: 225-491-0
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-08-08 18:06:34
What is apovincamine?
Originator
Apovincamine,GC Promochem
The Uses of apovincamine
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
Properties of apovincamine
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) |
form | neat |
color | Off-White to Pale Grey |
Safety information for apovincamine
Computed Descriptors for apovincamine
New Products
4-Aminotetrahydropyran-4-carbonitrile Hydrochloride (R)-3-Aminobutanenitrile Hydrochloride 4-AMINO-TETRAHYDRO-PYRAN-4-CARBOXYLIC ACID HCL 4-(Dimethylamino)tetrahydro-2H-pyran-4-carbonitrile 3-((Dimethylamino)methyl)-5-methylhexan-2-one oxalate 1,4-Dioxa-8-azaspiro[4.5]decane 5-Bromo-2-nitropyridine Nimesulide BP Aceclofenac IP/BP/EP Mefenamic Acid IP/BP/EP/USP Diclofenac Sodium IP/BP/EP/USP Ornidazole IP Diclofenac Potassium SODIUM AAS SOLUTION ZINC AAS SOLUTION BUFFER SOLUTION PH 10.0(BORATE) GOOCH CRUCIBLE SINTERED AQUANIL 5 BERYLLIUM AAS SOLUTION 2-Bromo-1-(bromomethyl)-3-chloro-5-nitrobenzene 2-Bromo-3-nitroaniline N-(3-Hydroxypropyl)-N-methylacetamide 3-Bromo-6-chloropyridazine 4-ethyl-3-nitrobenzoic acidRelated products of tetrahydrofuran
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