Isovaleramide

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

Isovaleramide

Names
IUPAC name 3-Methylbutanamide
Other names Isopentanamide Isovaleric acid amide Isovaleric amide beta-Methylbutyramide
Identifiers
CAS Number	541-46-8
3D model (JSmol)	Interactive image
ChemSpider	10467
ECHA InfoCard	100.007.984
EC Number	208-781-1
KEGG	D04637
PubChem CID	10930
UNII	9CP4KB634M
CompTox Dashboard (EPA)	DTXSID3060249
InChI InChI=1S/C5H11NO/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H2,6,7) Key: SANOUVWGPVYVAV-UHFFFAOYSA-N InChI=1/C5H11NO/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H2,6,7) Key: SANOUVWGPVYVAV-UHFFFAOYAT
SMILES CC(C)CC(=O)N
Properties
Chemical formula	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).
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Infobox references

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.[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 GABA_A receptor, similarly to isovaleric acid. [3]

References

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. doi:10.7705/biomedica.v30i2.187. PMID 20890571.