2-ethyl-3-methylpentanamide

• ChemBase ID: 130285
• Molecular Formular: C8H17NO
• Molecular Mass: 143.22668
• Monoisotopic Mass: 143.13101417
• SMILES: CCC(C)C(CC)C(=O)N
• Canonical SMILES: CCC(C(CC)C)C(=O)N
• InChI: InChI=1S/C8H17NO/c1-4-6(3)7(5-2)8(9)10/h6-7H,4-5H2,1-3H3,(H2,9,10)
• InChIKey: QRCJOCOSPZMDJY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-ethyl-3-methylpentanamide
• IUPAC Traditional name: nirvanil
• Synonyms: 2-ethyl-3-methyl-pentanamide; Axiquel; Nirvanil; Valnoctamide; Valnoctamide; 2-Ethyl-3-methylpentan-amide; 2-Ethyl-3-methylvaleramide; Valmethamide; McN-X-181

Database IDs

• CAS Number: 4171-13-5
• EC Number: 224-033-7
• MDL Number: MFCD00868184
• PubChem SID: 162224564
• PubChem CID: 20140
• ATC CODE: N05CM13
• CHEMBL: 1075733
• Chemspider ID: 18974
• KEGG ID: D02717
• MeSH Name: valnoctamide
• Unique Ingredient Identifier: 3O25NRX9YG
• Wikipedia Title: Valnoctamide

CALCULATED PROPERTIES

• Acid pKa: 17.088268
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 1.8339574
• LogD (pH = 7.4): 1.8339589
• Log P: 1.8339589
• Molar Refractivity: 42.0189 cm^3
• Polarizability: 16.67138 Å^3
• Polar Surface Area: 43.09 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: ≥10 mg/mL; Methanol
• Apperance: White crystals; White Solid; white to off-white powder
• Melting Point: 102-105°C0C
• Partition Coefficient: 1.885

Safety Information

• Storage Condition: desiccated; Refrigerator
• RTECS: YV5950000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; R22
• GHS Pictograms: GHS exclamation mark; GHS07
• GHS Signal Word: WARNING; Warning
• LD50: 760 mg kg^-1 (oral, rat)
• GHS Hazard statements: 302; H302
• Storage Temperature: room temp

Pharmacology Properties

• Admin Routes: Intravenous; Oral
• Bioavailability: 94%
• Half Life: 10 hours
• Metabolism: Hepatic

Product Information

• Purity: ≥98% (non-aqueous titration)
• Empirical Formula (Hill Notation): C8H17NO

DETAILS

Sigma Aldrich - V4765

Biochem/physiol Actions
Valproic acid (VPA) and derivatives such as valpromide and valnoctamide are anti-convulsant, mood stabilizing drugs, believed to function as indirect GABA agonists by inhibiting the transamination of GABA.

Toronto Research Chemicals - V094500

Isomer of Valpromide. Anxiolytic.

REFERENCES

• Bialer, M., et al.: Eur. J. Clin. Pharmacol., 38, 289 (1990)