ChemicalBook--->CAS DataBase List--->4171-13-5

4171-13-5

4171-13-5 Structure

4171-13-5 Structure
IdentificationBack Directory
[Name]

valnoctamide
[CAS]

4171-13-5
[Synonyms]

Axiquel
Nirvani
Nirvanil
NSC-32363
McN-X-181
valnoctamide
Valmethamide
2-Ethyl-3-methylvaleramide
2-Ethyl-3-methylpentan-amide
[EINECS(EC#)]

224-033-7
[Molecular Formula]

C8H17NO
[MDL Number]

MFCD00868184
[MOL File]

4171-13-5.mol
[Molecular Weight]

143.23
Chemical PropertiesBack Directory
[Appearance]

Crystalline Solid
[Melting point ]

113.5-1140C
[Boiling point ]

261.35°C (rough estimate)
[density ]

0.9636 (rough estimate)
[refractive index ]

1.4614 (estimate)
[storage temp. ]

Refrigerator
[solubility ]

DMSO: soluble20mg/mL, clear
[form ]

powder
[pka]

16.81±0.50(Predicted)
[color ]

white to off-white
[Water Solubility ]

8.70g/L(temperature not stated)
[InChI]

1S/C8H17NO/c1-4-6(3)7(5-2)8(9)10/h6-7H,4-5H2,1-3H3,(H2,9,10)
[InChIKey]

QRCJOCOSPZMDJY-UHFFFAOYSA-N
[SMILES]

CCC(C)C(CC)C(N)=O
Hazard InformationBack Directory
[Chemical Properties]

Crystalline Solid
[Uses]

Isomer of Valpromide. Anxiolytic
[Description]

Valnoctamide is an isomer of the valproic acid amide, valpromide. It has been marketed as an anxiolytic and sedative compound and suppresses neuropathic pain. Unlike valpromide, valnoctamide is not metabolized to its acid form, valnoctic acid, in vivo and has no teratogenicity. It abolishes the activity of myo-inositol-1-phosphate synthase in human brain crude homogenates (Ki = 0.18 mM). Valnoctamide suppresses electrographic seizures in animal models of status epilepticus, suggesting potential applications in managing epilepsy.
[Definition]

ChEBI: Valnoctamide is a fatty amide.
[Brand name]

Axiquel (Ortho-McNeil).
[References]

[1] ROGAWSKI M A. Diverse mechanisms of antiepileptic drugs in the development pipeline[J]. Epilepsy Research, 2006, 69 3: Pages 273-294. DOI: 10.1016/j.eplepsyres.2006.02.004
[2] ILAN WINKLER. Efficacy of antiepileptic isomers of valproic acid and valpromide in a rat model of neuropathic pain[J]. British Journal of Pharmacology, 2009, 146 2: 198-208. DOI: 10.1038/sj.bjp.0706310
[3] GALIT SHALTIEL. Effect of valproate derivatives on human brain myo-inositol-1-phosphate (MIP) synthase activity and amphetamine-induced rearing.[J]. Pharmacological Reports, 2007, 59 4: 402-407.
[4] JAY SPAMPANATO  F. E D. Valnoctamide enhances phasic inhibition: A potential target mechanism for the treatment of benzodiazepine-refractory status epilepticus[J]. Epilepsia, 2014, 55 9: e94-e98. DOI: 10.1111/epi.12702
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

22
[WGK Germany ]

3
[RTECS ]

YV5950000
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Acute Tox. 4 Oral
[Toxicity]

LD50 oral in rat: 760mg/kg
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