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V4765

Sigma-Aldrich

Valnoctamide

≥98% (NMR)

Synonym(s):

2-ethyl-3-methyl-pentanamide, Axiquel, Nirvanil

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About This Item

Empirical Formula (Hill Notation):
C8H17NO
CAS Number:
4171-13-5
Molecular Weight:
143.23
MDL number:
MFCD00868184
UNSPSC Code:
12352200
PubChem Substance ID:
329829054
NACRES:
NA.77

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

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
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Amidic derivatives of valproic acid as antiviral in HSV-1-infected oligodendrocytes.
Praena B, et al.
Antiviral Research, 54(29), 99-102 (2019)
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
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
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