Basic information
- CAS
42971-09-5- Standard SMILES
CCOC(=O)C1=C[C@]2(CC)CCCN3CCc4c(n1c1ccccc41)[C@@H]32- InChIKey
DDNCQMVWWZOMLN-IRLDBZIGSA-N- Molecular formula
- C22H26N2O2
- Average molar mass
- 350.5 g/mol
- Monoisotopic mass
- 350.19942807
Overview
Vinpocetine is an alkaloid. It has a role as a geroprotector.
Names & identifiers
- Preferred name
- Vinpocetine
- IUPAC
- ethyl (15S,19S)-15-ethyl-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18),16-pentaene-17-carboxylate
- English name
- Vinpocetine
- Molecular formula
- C22H26N2O2
- Molecular weight
- 350.46
Names & synonyms
vinpocetine42971-09-5CavintonCeractinBravintonVinporalApovincaminic acid ethyl esterEthyl apovincamin-22-oateUltra-VincaVinpocetinumRGH 4405cis-Apovincaminic acid ethyl ester
Show more names
VINPOCETINAppearanceEBURNAMENINEEthyl apovincaminate(3alpha,16alpha)-Eburnamenine-14-carboxylic acid ethyl esterTcv-3BCS-1570RGH-4405
Ethyl (+)-cis-apovincaminateTCV 3BVinpocetinaDTXSID5023740NSC-760093AY-27,255543512OBTCAY-27255
Database identifiers
- CAS
42971-09-5- PubChem CID
- 443955
- DTXSID
DTXSID5023740- ChEMBL
CHEMBL71752- ChEBI
CHEBI:32297- UNII
- 543512OBTC
Properties
Computed structural properties
- XLogP
- 4.1
- Topological polar surface area
- 34.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 4
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 617
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP4.23
Solubility35.5 [ug/mL] (The mean of the results at pH 7.4)
Dietary IngredientsVinpocetine
Dissociation Constants7.1
Physicochemical properties
- Melting point
- 147 · 147-153 °C dec.
- alpha
- 20 · D20 +114° (c = 1 in pyridine)
- Boiling point
- 484.44 °C · 484.44°C (rough estimate)
- Density
- 1.126 · 1.1260 (rough estimate)
- refractive index
- 1.65 · 1.6500 (estimate)
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- 5 mg/mL · DMSO: 5 mg/mL
- form
- solid
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 48 reports by companies from 3 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- JW4792000
- hs_code
- 29399990
- Toxicity
- LD50 in mice, rats (mg/kg): 534, 503 orally; 240, 133.8 i.p.; 58.7, 42.6 i.v. (Pálosi, Szporny), also reported as 161.2 mg/kg i.p. in mice (Cholnoky, Dmk)
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P264-P270-P301+P312-P501
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
MeSH Pharmacological Classification
Compounds which inhibit or antagonize the biosynthesis or actions of phosphodiesterases.
Drugs used to cause dilation of the blood vessels.
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.
Applications
DescriptionVinpocetine (42971-09-5) is a phosphodiesterase PDE1 inhibitor (IC50=21 μM).1Also blocks voltage-gated Na+channels, IC50=44.2 μM (potency similar to phenytoin), a mechanism which may contribute to its neuroprotective and anticonvulsant activity.2It reduces inflammatory IL-1β and TNF-α expression in rat hippocampus.3Displays beneficial effects in a rat model of cerebral ischemia-reperfusion injury.4Vinpocetine exerts neuroprotective effects by suppressing microglial inflammation.5
UsesA calcium/calmodulin-dependent phosphodiesterase 1 (PDE1) inhibitor
UsesA derivative of Vincamine with vasodilating activity. Vasodilator (cerebral).
Usescalcium regulator
UsesGleevec metabolite, tyrosine kinase inhibitor
Preparation methods
Production MethodVincamine extracted from small periwinkle (Vinca mino) of apocynaceae plant as raw material, dehydration to Apovincamine, then hydrolysis to Apovincaminic acid. Dissolved the acid (1.0 g, 0.003 mo1) and 1.0 g of potassium hydroxide in 80 ml of drying ethanol, add bromine ethane (0.4 g, 0.0036 mol), reflux 3 h. After the completion of reaction, cooling, evaporation to dry. Dissolve the leftovers in 500 ml of 2% sulfuric acid, and adjust the Ph to 8. Extracted with methylene chloride, drying with potassium carbonate, after the majority of methylene chloride has been evaporated, add in ethanol. Be placed overnight At 0 oC, filter the collected precipitation crystallization, washing with cold ethanol, drying, 0.66 g of Vinpocetine could be obtained. Tabersonine extracted from apocynaceae plant willow small licorice leaf or periwinkle seed can also be as raw material, through multi-step synthesis.
Related reactions
4 records
Compound notes
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