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V4765

Sigma-Aldrich

Valnoctamide

≥98% (NMR)

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Synonym(s):
2-ethyl-3-methyl-pentanamide, Axiquel, Nirvanil
Empirical Formula (Hill Notation):
C8H17NO
CAS Number:
Molecular Weight:
143.23
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (NMR)

form

powder

storage condition

desiccated

color

white to off-white

solubility

DMSO: 20 mg/mL, clear

storage temp.

room temp

SMILES string

CCC(C)C(CC)C(N)=O

InChI

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

InChI key

QRCJOCOSPZMDJY-UHFFFAOYSA-N

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This Item
V3640SML1503SML1624
Valnoctamide ≥98% (NMR)

V4765

Valnoctamide

Valpromide ≥97% (NMR)

V3640

Valpromide

Apcin ≥98% (HPLC)

SML1503

Apcin

Sigma-Aldrich

SML1624

JNJ-63533054

form

powder

form

powder

form

powder

form

powder

storage temp.

room temp

storage temp.

room temp

storage temp.

room temp

storage temp.

room temp

solubility

DMSO: 20 mg/mL, clear

solubility

DMSO: >10 mg/mL

solubility

DMSO: 25 mg/mL, clear

solubility

DMSO: 20 mg/mL, clear

storage condition

desiccated

storage condition

-

storage condition

-

storage condition

-

color

white to off-white

color

white to off-white

color

white to beige

color

white to beige

Application

Valnoctamide has been used:
  • as a mood stabilizer to study its anti-cytomegalovirus (anti-CMV) effects in newborn mice brain
  • as a hypnotic sedative to study its cytotoxic effects on oligodendrocyte precursor cells (OPCs) and human oligodendroglioma cell line (HOG)
  • as a mood stabilizer to study its effects on inhibition of human cytomegalovirus

Biochem/physiol Actions

Valnoctamide exhibits anti-cytomegalovirus (anti-CMV) properties. It has therapeutic effects against status epilepticus (SE) and neuropathic pain. Valnoctamide also shows therapeutic effects against bipolar disorders.
Valproic acid (VPA) and derivatives such as valpromide and valnoctamide are anti-convulsant, mood stabilizing drugs, believed to function as indirect GABA agonists by inhibiting the transamination of GABA.

Features and Benefits

This compound is featured on the Glutamate/GABA Synthesis and Metabolism page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

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Mood stabilizers inhibit cytomegalovirus infection
Ornaghi S, et al.
Virology, 499(29), 121-135 (2016)
M Bialer
Journal of controlled release : official journal of the Controlled Release Society, 62(1-2), 187-192 (1999-10-16)
Valproic acid (VPA) is one of the major antiepileptic drugs. However, its anticonvulsant potency is less than the other three major antiepileptic drugs. Furthermore, VPA causes two rare but severe side effects: teratogenicity and hepatotoxicity. We utilized pharmacokinetic considerations in
M Radatz et al.
Epilepsy research, 30(1), 41-48 (1998-04-29)
The teratogenic properties of valproic acid (VPA) and its analogues depend to a great extent on their chemical structure. We investigated the structure-teratogenicity relationships of VPA, its structural isomer, valnoctic acid (VCA), and their two amide analogues, valpromide (VPD) and
Valnoctamide and sec-butyl-propylacetamide (SPD) for acute seizures and status epilepticus
Shekh A T, et al.
Epilepsia, 54(29), 99-102 (2013)
F Pisani et al.
Epilepsia, 34(5), 954-959 (1993-09-01)
Six patients stabilized with carbamazepine (CBZ) therapy received an 8-day "add-on" supplement of valnoctamide (VCD), a tranquilizer available over the counter (OTC) in several European countries that exhibits promising anticonvulsant activity in animal models. During VCD intake, serum levels of

Articles

Glutamine is a common precursor for the biosynthesis of both glutamate and GABA. Glutamine can be transported in and out of neurons and astrocytes utilizing different glutamine carriers. The neurotransmitter glutamate can be synthesized from glutamine by the action of phosphate-activated glutaminase.

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