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

• ChemBase ID: 130416
• Molecular Formular: C22H26N2O2
• Molecular Mass: 350.45404
• Monoisotopic Mass: 350.19942808
• SMILES: O=C(OCC)C1=C[C@]2([C@H]3c4n1c1c(c4CCN3CCC2)cccc1)CC
• Canonical SMILES: CCOC(=O)C1=C[C@]2(CC)CCCN3[C@@H]2c2n1c1ccccc1c2CC3
• InChI: InChI=1S/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

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (15S,19S)-15-ethyl-1,11-diazapentacyclo[9.6.2.0^2,^7.0^8,^1^8.0^1^5,^1^9]nonadeca-2,4,6,8(18),16-pentaene-17-carboxylate
• IUPAC Traditional name: vinpocetine
• Synonyms: Vinpocetine; (3α,16α)-Eburnamenine-14-carboxylic acid ethyl ester; Eburnamenine-14-carboxylic acid ethyl ester; Vinpocetine

Database IDs

• CAS Number: 42971-09-5
• EC Number: 256-028-0
• MDL Number: MFCD00211233
• PubChem SID: 162224695; 24278182
• PubChem CID: 443955
• ATC CODE: N06BX18
• CHEMBL: 71752
• Chemspider ID: 392007
• KEGG ID: D01371
• Unique Ingredient Identifier: 543512OBTC
• Wikipedia Title: Vinpocetine

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.3386369
• LogD (pH = 7.4): 3.843793
• Log P: 4.0670204
• Molar Refractivity: 104.2384 cm^3
• Polarizability: 41.198402 Å^3
• Polar Surface Area: 34.47 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble5 mg/mL; H2O: insoluble
• Apperance: white solid

Safety Information

• RTECS: JW4792000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Admin Routes: oral, intravenous
• Bioavailability: 56.6 +/- 8.9%
• Excretion: renal
• Half Life: 2.54 +/- 0.48 hours
• Metabolism: hepatic
• Legal Status: OTC
• Pregnancy Category: not recommended
• Gene Information: human ... PDE1A(5136), PDE1B(5153), PDE1C(5137)

Product Information

• Purity: ≥98%

DETAILS

Sigma Aldrich - V6383

Biochem/physiol Actions
Ca2+-calmodulin-dependent phosphodiesterase I (PDE1) inhibitor.
Caution
Photosensitive