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V4765

Sigma-Aldrich

Valnoctamide

≥98% (NMR)

Synonyme(s) :

2-ethyl-3-methyl-pentanamide, Axiquel, Nirvanil

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About This Item

Formule empirique (notation de Hill):
C8H17NO
Numéro CAS:
4171-13-5
Poids moléculaire :
143.23
Numéro MDL:
MFCD00868184
Code UNSPSC :
12352200
ID de substance PubChem :
329829054
Nomenclature NACRES :
NA.77

Pureté

≥98% (NMR)

Forme

powder

Conditions de stockage

desiccated

Couleur

white to off-white

Solubilité

DMSO: 20 mg/mL, clear

Température de stockage

room temp

Chaîne SMILES 

CCC(C)C(CC)C(N)=O

InChI

1S/C8H17NO/c1-4-6(3)7(5-2)8(9)10/h6-7H,4-5H2,1-3H3,(H2,9,10)

Clé InChI

QRCJOCOSPZMDJY-UHFFFAOYSA-N

Application

Valnoctamide has been used:
  • as a mood stabilizer to study its anti-cytomegalovirus (anti-CMV) effects in newborn mice brain
  • as a hypnotic sedative to study its cytotoxic effects on oligodendrocyte precursor cells (OPCs) and human oligodendroglioma cell line (HOG)
  • as a mood stabilizer to study its effects on inhibition of human cytomegalovirus

Actions biochimiques/physiologiques

Valnoctamide exhibits anti-cytomegalovirus (anti-CMV) properties. It has therapeutic effects against status epilepticus (SE) and neuropathic pain. Valnoctamide also shows therapeutic effects against bipolar disorders.
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.

Caractéristiques et avantages

This compound is featured on the Glutamate/GABA Synthesis and Metabolism page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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H Steve White et al.
Epilepsia, 53(1), 134-146 (2011-12-14)
sec-Butyl-propylacetamide (SPD) is a one-carbon homolog of valnoctamide (VCD), a central nervous system (CNS)-active amide derivative of valproic acid (VPA) currently in phase II clinical trials. The study reported herein evaluated the anticonvulsant activity of SPD in a battery of
A Haj-Yehia et al.
Journal of pharmaceutical sciences, 77(10), 831-834 (1988-10-01)
Valnoctamide (2-ethyl-3-methylpentanamide; VCD), an isomer of valpromide possessing both anxiolytic and antiepileptic properties, has been used as a tranquilizer in the treatment of anxiety and tension. As VCD is an isomer of valpromide (VPD), which is used both as an
Rapid gas chromatographic assay for monitoring valnoctamide in plasma.
M Bialer et al.
Journal of chromatography, 337(2), 408-411 (1985-02-08)
S Barel et al.
Clinical pharmacology and therapeutics, 61(4), 442-449 (1997-04-01)
To investigate the pharmacokinetics of the four stereoisomers of valnoctamide, a mild tranquilizer endowed with anticonvulsant properties. Racemic valnoctamide, 400 mg, was administered orally to seven healthy subjects and to six patients with epilepsy stabilized with long-term carbamazepine therapy. In
F Pisani et al.
British journal of clinical pharmacology, 34(1), 85-87 (1992-07-01)
The effect of the valpromide isomer valnoctamide (VCD, 200 mg three times daily for 8 days), an over-the-counter tranquillizer, on the elimination kinetics of a single oral dose of carbamazepine-10, 11-epoxide (CBZ-E, 100 mg) was investigated in healthy subjects. During
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Glutamate/GABA Synthesis and Metabolism

Glutamine is a common precursor for the biosynthesis of both glutamate and GABA. Glutamine can be transported in and out of neurons and astrocytes utilizing different glutamine carriers. The neurotransmitter glutamate can be synthesized from glutamine by the action of phosphate-activated glutaminase.

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