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Vinpocetine(CAS No. 42971-09-5)

Vinpocetine C22H26N2O2 (cas 42971-09-5) Molecular Structure

42971-09-5 Structure

Identification and Related Records

【Name】
Vinpocetine
【CAS Registry number】
42971-09-5
【Synonyms】
(+)-Apovincaminic acid ethyl ester
(+)-Vinpocetine
(+)-cis-Apovincaminic acid ethyl ester
AY 27255
Apovincaminic acid ethyl ester
Bravinton
Cavinton
Ceractin
Ethyl(+)-apovincaminate
Ethyl (+)-cis-apovincaminate
Ethyl apovincaminate
RGH4405
TCV 3B
Ultra-Vinca
Vinpocetinum
Vinporal
cis-Apovincaminic acid ethylester
【EINECS(EC#)】
256-028-0
【Molecular Formula】
C22H26N2O2 (Products with the same molecular formula)
【Molecular Weight】
350.45
【Inchi】
InChI=1/C22H26N2O2/c1-3-22-11-7-12-23-13-10-16-15-8-5-6-9-17(15)24(19(16)20(22)23)18(14-22)21(25)26-4-2/h5-6,8-9,14,20H,3-4,7,10-13H2,1-2H3/t20-,22+/m1/s1
【InChIKey】
DDNCQMVWWZOMLN-IRLDBZIGSA-N
【Canonical SMILES】
CCC12CCCN3C1C4=C(CC3)C5=CC=CC=C5N4C(=C2)C(=O)OCC
【Isomers smiles】
CC[C@@]12CCCN3[C@@H]1C4=C(CC3)C5=CC=CC=C5N4C(=C2)C(=O)OCC
【MOL File】
42971-09-5.mol

Chemical and Physical Properties

【Appearance】
White Crystalline Solid
【Density】
1.28 g/cm3
【Melting Point】
147-153 °C dec
【Boiling Point】
419.5 °C at 760 mmHg
【Flash Point】
207.5 °C
【Water】
DMSO: 5 mg/mL
【Solubilities】
DMSO: 5 mg/mL
【Color/Form】
white
【Stability】
Stable at normal temperatures and pressures.
【Storage temp】
Keep tightly closed.
【Computed Properties】
Molecular Weight:350.45404 [g/mol]
Molecular Formula:C22H26N2O2
XLogP3-AA:4.1
H-Bond Donor:0
H-Bond Acceptor:3
Rotatable Bond Count:4
Exact Mass:350.199428
MonoIsotopic Mass:350.199428
Topological Polar Surface Area:34.5
Heavy Atom Count:26
Formal Charge:0
Complexity:617
Isotope Atom Count:0
Defined Atom Stereocenter Count:2
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Feature 3D Cation Count:2
Feature 3D Hydrophobe Count:1
Feature 3D Ring Count:5
Effective Rotor Count:5
Conformer Sampling RMSD:0.8
CID Conformer Count:7

Safety and Handling

【Hazard Codes】
Xn:Harmful
【Risk Statements】
R22
【Safety Statements 】
S36
【Safety】

Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion. Experimental teratogenic and reproductive effects. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: Xn
Risk Statements: 22
22:? Harmful if swallowed?
Safety Statements: 36
36:? Wear suitable protective clothing?
WGK Germany: 3
RTECS: JW4792000

【Specification】

? Vinpocetinum , with CAS number of 42971-09-5, can be called Ethyl (+)-cis-apovincaminate ; Ethyl(+)-apovincaminate ; cis-Apovincaminic acid ethylester ; Apovincaminic acid ethyl ester ; (+)-cis-Apovincaminic acid ethyl ester ; 1H-Indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine,eburnamenine-14-carboxylic acid deriv ; (+)-Apovincaminic acid ethyl ester . It is a?white crystalline solid,?Vinpocetinum (CAS NO.42971-09-5) is used as a vasodilator.

Use and Manufacturing

【Usage】

A calcium/calmodulin-dependent phosphodiesterase 1 (PDE1) inhibitor

Biomedical Effects and Toxicity

【Biological Activity】
Phosphodiesterase inhibitor, selective for PDE1 (IC 50 = 21 μ M). Also blocks voltage-gated Na + channels.
【Pharmacological Action】
- Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids.
- Drugs used to specifically facilitate learning or memory, particularly to prevent the cognitive deficits associated with dementias. These drugs act by a variety of mechanisms. While no potent nootropic drugs have yet been accepted for general use, several are being actively investigated.
- Compounds which inhibit or antagonize the biosynthesis or actions of phosphodiesterases.
- Drugs used to cause dilation of the blood vessels.

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