Isovaleramide

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Isovaleramide
Skeletal formula of isovaleramide
Ball-and-stick model of isovaleramide
Names
Preferred IUPAC name
3-Methylbutanamide
Other names
Isopentanamide
Isovaleric acid amide
Isovaleric amide
beta-Methylbutyramide
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.007.984 Edit this at Wikidata
EC Number
  • 208-781-1
KEGG
UNII
  • InChI=1S/C5H11NO/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H2,6,7) ☒N
    Key: SANOUVWGPVYVAV-UHFFFAOYSA-N ☒N
  • InChI=1/C5H11NO/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H2,6,7)
    Key: SANOUVWGPVYVAV-UHFFFAOYAT
  • CC(C)CC(=O)N
Properties
C5H11NO
Molar mass 101.149 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).
☒N verify (what is checkY☒N ?)

Isovaleramide is an

isovaleric acid
, it is a colourless solid.

Occurrence and biological activity

Isovaleramide is a constituent of

valerian root
.

In humans, it acts as a mild

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

  1. ^ US 5506268, Balandrin, Manuel F. & Van Wagenen, Bradford C., "Use of isovaleramide as a mild anxiolytic and sedative agent", published 1996-04-09, assigned to NPS Pharmaceuticals Inc. 
  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. PMID 20890571
    .
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