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Isovaleramide

In today's article, we will explore the topic of Isovaleramide in depth, analyzing its importance in different contexts and its relevance in today's society. From its origins to its evolution over time, Isovaleramide has been the subject of study and debate, influencing thought and popular culture. Through an exhaustive analysis, we will address the different aspects that make up Isovaleramide, examining its impact on various areas of daily life. With data, studies and relevant information, we aim to offer a comprehensive view on Isovaleramide, providing our readers with an enriching and novel perspective on this topic.
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).
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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.
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