Isovaleramide

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Isovaleramide
Isovaleramide.png
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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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-781-1
KEGG
PubChem CID
UNII
  • InChI=1S/C5H11NO/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H2,6,7) X mark.svgN
    Key: SANOUVWGPVYVAV-UHFFFAOYSA-N X mark.svgN
  • 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
Appearancecolourless 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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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. [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 GABAA receptor, similarly to isovaleric acid. [3]

Related Research Articles

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Valerian is a perennial flowering plant native to Europe and Asia. In the summer when the mature plant may have a height of 1.5 metres, it bears sweetly scented pink or white flowers that attract many fly species, especially hoverflies of the genus Eristalis. It is consumed as food by the larvae of some Lepidoptera species, including the grey pug.

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Clobazam Benzodiazepine class medication

Clobazam, sold under the brand names Frisium, Onfi and others, is a benzodiazepine class medication that was patented in 1968. Clobazam was first synthesized in 1966 and first published in 1969. Clobazam was originally marketed as an anxioselective anxiolytic since 1970, and an anticonvulsant since 1984. The primary drug-development goal was to provide greater anxiolytic, anti-obsessive efficacy with fewer benzodiazepine-related side effects.

Clomethiazole Sedative and anti-hypnotic medication

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3-Methylbutanoic acid Carboxylic acid with chemical formula (CH3)2CHCH2CO2H CH3CH2

3-Methylbutanoic acid, also known as β-methylbutyric acid or more commonly isovaleric acid, is a branched-chain alkyl carboxylic acid with the chemical formula (CH3)2CHCH2CO2H. It is classified as a short-chain fatty acid. Like other low-molecular-weight carboxylic acids, it has an unpleasant odor. The compound occurs naturally and can be found in many foods, such as cheese, soy milk, and apple juice.

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Hexethal

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GABA receptor agonist

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Imidazenil Chemical compound

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Y-23684

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NS-2664

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NS-2710

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Barbiturate Class of sedative medication derived from barbituric acid

A barbiturate is a drug that acts as a central nervous system depressant. Barbiturates are effective as anxiolytics, hypnotics, and anticonvulsants, but have physical and psychological addiction potential as well as overdose potential among other possible adverse effects. They have largely been replaced by benzodiazepines and nonbenzodiazepines ("Z-drugs") in routine medical practice, particularly in the treatment of anxiety and insomnia, due to the significantly lower risk of addiction and overdose and the lack of an antidote for barbiturate overdose. Despite this, barbiturates are still in use for various purposes: in general anesthesia, epilepsy, treatment of acute migraines or cluster headaches, acute tension headaches, euthanasia, capital punishment, and assisted suicide.

HA-966

HA-966 or (±) 3-Amino-1-hydroxy-pyrrolidin-2-one is a molecule used in scientific research as a glycine receptor and NMDA receptor antagonist / low efficacy partial agonist. It has neuroprotective and anticonvulsant, anxiolytic, antinociceptive and sedative / hypnotic effects in animal models. Pilot human clinical trials in the early 1960s showed that HA-966 appeared to benefit patients with tremors of extrapyramidal origin.

GABA analogue Class of drugs

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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 . PMID   20890571.