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Valnoctamide

Names

[ CAS No. ]:
4171-13-5

[ Name ]:
Valnoctamide

[Synonym ]:
2-ethyl-3-methylpentanamide
Valnoctamide

Biological Activity

[Description]:

Valnoctamide (Valmethamide), a derivative of valproate, suppresses benzodiazepine-refractory status epilepticus. Valnoctamide (Valmethamide) acts directly on GABAA receptors[1].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> GABA Receptor
Research Areas >> Neurological Disease
Signaling Pathways >> Neuronal Signaling >> GABA Receptor

[Target]

GABAA receptor[1]


[References]

[1]. Spampanato J, et al. Valnoctamide enhances phasic inhibition: a potential target mechanism for the treatment of benzodiazepine-refractory status epilepticus. Epilepsia. 2014 Sep;55(9):e94-8.

Chemical & Physical Properties

[ Density]:
0.883g/cm3

[ Boiling Point ]:
274.4ºC at 760mmHg

[ Melting Point ]:
113.5-114ºC

[ Molecular Formula ]:
C8H17NO

[ Molecular Weight ]:
143.22700

[ Flash Point ]:
119.8ºC

[ Exact Mass ]:
143.13100

[ PSA ]:
43.09000

[ LogP ]:
2.24430

[ Index of Refraction ]:
1.438

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
YV5950000
CHEMICAL NAME :
Valeramide, 2-ethyl-3-methyl-
CAS REGISTRY NUMBER :
4171-13-5
BEILSTEIN REFERENCE NO. :
1749434
LAST UPDATED :
199612
DATA ITEMS CITED :
6
MOLECULAR FORMULA :
C8-H17-N-O
MOLECULAR WEIGHT :
143.26
WISWESSER LINE NOTATION :
ZVY2&Y2&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
760 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
27ZQAG "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972 Volume(issue)/page/year: -,429,1972
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
580 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
27ZQAG "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972 Volume(issue)/page/year: -,429,1972
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
999 mg/kg
TOXIC EFFECTS :
Behavioral - altered sleep time (including change in righting reflex) Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 62,404,1966
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
540 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
27ZQAG "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972 Volume(issue)/page/year: -,429,1972 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
700 mg/kg
SEX/DURATION :
female 6-12 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - abortion
REFERENCE :
CRSBAW Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. (SPPIF, B.P.22, F-41353 Vineuil, France) V.1- 1849- Volume(issue)/page/year: 159,6,1965
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
600 mg/kg
SEX/DURATION :
female 6-8 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
REFERENCE :
CRSBAW Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. (SPPIF, B.P.22, F-41353 Vineuil, France) V.1- 1849- Volume(issue)/page/year: 159,6,1965

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
YV5950000

[ HS Code ]:
2924199090

Synthetic Route

Precursor & DownStream

Customs

[ HS Code ]: 2924199090

[ Summary ]:
2924199090. other acyclic amides (including acyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

Structure activity relationship of human microsomal epoxide hydrolase inhibition by amide and acid analogues of valproic acid.

Pharm. Res. 17(2) , 216-21, (2000)

The purpose of this study was to evaluate the in vitro inhibitory potency of various amide analogues and derivatives of valproic acid toward human microsomal epoxide hydrolase (mEH).mEH inhibition was...

A comparative electrographic analysis of the effect of sec-butyl-propylacetamide on pharmacoresistant status epilepticus.

Neuroscience 231 , 145-56, (2013)

Better treatment of status epilepticus (SE), which typically becomes refractory after about 30 min, will require new pharmacotherapies. The effect of sec-butyl-propylacetamide (SPD), an amide derivati...

Amidic modification of valproic acid reduces skeletal teratogenicity in mice.

Birth Defects Res. B Dev. Reprod. Toxicol. 71(1) , 47-53, (2004)

The antiepileptic drug valproic acid (VPA) is well known to cause neural tube and skeletal defects in both humans and animals. The amidic VPA analogues valpromide (VPD) and valnoctamide (VCD) have muc...


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