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Isovaleramide
Names
Preferred IUPAC name
Other names
Isopentanamide Isovaleric acid amide Isovaleric amide beta-Methylbutyramide
Identifiers
ChemSpider
ECHA InfoCard
100.007.984
EC Number
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
Properties
C 5 H 11 N O
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).
Chemical compound
Isovaleramide is an
organic compound with the formula (CH3 )2 CHCH2 C(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]
References
^
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.
^ 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.
^ 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 .
Alcohols
Barbiturates
Benzodiazepines
Carbamates
Flavonoids
Imidazoles
Kava constituents
Monoureides
Neuroactive steroids
Nonbenzodiazepines
Phenols
Piperidinediones
Pyrazolopyridines
Quinazolinones
Volatiles /
gases Others/unsorted
3-Hydroxybutanal
α-EMTBL
AA-29504
Alogabat
Avermectins (e.g.,
ivermectin )
Bromide compounds (e.g.,
lithium bromide ,
potassium bromide ,
sodium bromide )
Carbamazepine
Chloralose
Chlormezanone
Clomethiazole
Darigabat
DEABL
Deuterated etifoxine
Dihydroergolines (e.g.,
dihydroergocryptine ,
dihydroergosine ,
dihydroergotamine ,
ergoloid (dihydroergotoxine) )
DS2
Efavirenz
Etazepine
Etifoxine
Fenamates (e.g.,
flufenamic acid ,
mefenamic acid ,
niflumic acid ,
tolfenamic acid )
Fluoxetine
Flupirtine
Hopantenic acid
KRM-II-81
Lanthanum
Lavender oil
Lignans (e.g.,
4-O-methylhonokiol ,
honokiol ,
magnolol ,
obovatol )
Loreclezole
Menthyl isovalerate (validolum)
Monastrol
Niacin
Niacinamide
Org 25,435
Phenytoin
Propanidid
Retigabine (ezogabine)
Safranal
Seproxetine
Stiripentol
Sulfonylalkanes (e.g.,
sulfonmethane (sulfonal) ,
tetronal ,
trional )
Terpenoids (e.g.,
borneol )
Topiramate
Valerian constituents (e.g.,
isovaleric acid ,
isovaleramide ,
valerenic acid ,
valerenol )