Isovaleramide

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Isovaleramide
Skeletal formula of isovaleramide
Ball-and-stick model of isovaleramide
Names
IUPAC name
3-Methylbutanamide
Other names
Isopentanamide
Isovaleric acid amide
Isovaleric amide
beta-Methylbutyramide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.984
EC Number 208-781-1
KEGG
UNII
Properties
C5H11NO
Molar mass 101.15 g·mol−1
Appearance colourless solid
Melting point 137 °C (279 °F; 410 K)
Boiling point 226 °C (439 °F; 499 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Isovaleramide is an organic compound with the formula (CH3)2CHCH2C(O)NH2. The amide derived from isovaleric acid, it is a colourless solid.

Occurrence and biological activity[edit]

Isovaleramide is a constituent of valerian root.

In humans, it acts as a mild anxiolytic at lower doses and as a mild sedative at higher dosages.[1] Isovaleramide has been shown to be non-cytotoxic and does not act as a CNS stimulant. It inhibits the liver alcohol dehydrogenases and has a reported LD50 of greater than 400 mg/kg when administered intraperitoneally in mice.[2]

It is a positive allosteric modulator of the GABAA receptor, similarly to isovaleric acid. [3]

References[edit]

  1. ^ "Use of isovaleramide as a mild anxiolytic and sedative agent", US 5506268 
  2. ^ Taillandier, Georges; Benoit-Guyod, Jean L.; Boucherle, Andre; Broll, Madeleine; Eymard, Pierre (1975). "Dipropylacetic series. XII. Anticonvulsant branched aliphatic acids and alcohols". European Journal of Medicinal Chemistry. 10 (5): 453–462. 
  3. ^ Giraldo SE, Rincón J, Puebla P, Marder M, Wasowski C, Vergel N, Guerrero MF (2010). "[Isovaleramide, an anticonvulsant molecule isolated from Valeriana pavonii]". Biomedica (in Spanish). 30 (2): 245–50. PMID 20890571.