Isovaleramide

Nowadays, Isovaleramide is an issue that affects a large number of people around the world. With the advancement of technology and globalization, Isovaleramide has become a topic of great relevance in our society. Whether in the personal, family, work or social sphere, Isovaleramide impacts people's lives in different ways. In this article, we will thoroughly explore the impact of Isovaleramide and discuss different perspectives and solutions to address this important issue today.

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 , 100 kPa).
☒N verify (what is checkY☒N ?)

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

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. 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.

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

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. ^ 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. doi:10.7705/biomedica.v30i2.187. hdl:11336/18247. PMID 20890571.