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Isovaleramide

From Wikipedia, the free encyclopedia
Isovaleramide
Skeletal formula of isovaleramide
Skeletal formula of isovaleramide
Ball-and-stick model 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 InfoCard100.007.984Edit 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 mass101.149 g·mol−1
Appearancecolourless solid
Melting point137 °C (279 °F; 410 K)
Boiling point226 °C (439 °F; 499 K)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Isovaleramide is anorganic compound with the formula (CH3)2CHCH2C(O)NH2. Theamide derived fromisovaleric acid, it is a colourless solid.

Occurrence and biological activity

[edit]

Isovaleramide is a constituent ofvalerian root.

In humans, it acts as a mildanxiolytic at lower doses and as a mildsedative at higher dosages.[1] Isovaleramide has been shown to be non-cytotoxic and does not act as aCNS stimulant. It inhibits theliveralcohol dehydrogenases and has a reportedLD50 of greater than 400 mg/kg when administeredintraperitoneally in mice.[2]

It is apositive allosteric modulator of theGABAA receptor, similarly to isovaleric acid.[3]

References

[edit]
  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 toNPS 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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