NIALAMIDE

NIALAMIDE Basic information
Product Name:NIALAMIDE
Synonyms:N-BENZYL-BETA-[ISONICOTINYL-HYDRAZINE] PROPIONAMIDE;N-BENZYL-BETA-(ISONICOTINYLHYDRAZINO)PROPIONAMIDE;NIALAMIDE;N-ISONICOTINOYL-N' [BETA-(N-BENZYL-CARBOXAMIDO) ETHYL] HYDRAZINE;1-(2-(benzylcarbamoyl)ethyl)-2-isonicotinoylhydrazine;1-[2-(Benzylcarbamoyl)ethyl]-2-isonicotinoylhydrazine;2-(2-(Benzylcarbamoyl)ethyl)hydrazide, isonicotinic acid;2-(2-(Benzylcarbamyl)ethyl)hydrazide isonicotinic acid
CAS:51-12-7
MF:C16H18N4O2
MW:298.34
EINECS:200-079-3
Product Categories:NIAMID
Mol File:51-12-7.mol
NIALAMIDE Structure
NIALAMIDE Chemical Properties
Melting point 152-154 °C(lit.)
Boiling point 439.76°C (rough estimate)
density 1.1183 (rough estimate)
refractive index 1.6000 (estimate)
storage temp. −20°C
solubility ethanol: clear to hazy
pka11.13±0.23(Predicted)
Merck 13,6515
BRN 492941
Safety Information
Hazard Codes Xn
Risk Statements 20/21/22-36/37/38-40
Safety Statements 22-26-36
RIDADR 3249
WGK Germany 3
RTECS NS1225000
10
HazardClass 6.1(b)
PackingGroup III
Hazardous Substances Data51-12-7(Hazardous Substances Data)
ToxicityLD50 in mice, rats (mg/kg): 1000, 1700 orally; 742, 760 i.p. (Delahunt)
MSDS Information
ProviderLanguage
SigmaAldrich English
NIALAMIDE Usage And Synthesis
Chemical PropertiesWhite, crystalline powder. Low solubility in water; good solubility in slightly acid solution. It is stable in crystalline form, suspension, and solution.
OriginatorNiamid,Pfizer,US,1959
UsesMAO inhibitor
UsesNialamide is a nonselective monoamine oxidase (MAO) inhibitor that is used as an antidepressant.
DefinitionChEBI: 3-[[oxo(pyridin-4-yl)methyl]hydrazo]-N-(phenylmethyl)propanamide is an organooxygen compound and an organonitrogen compound. It is functionally related to a beta-amino acid.
Manufacturing ProcessMethyl acrylate, 28.0 g (0.4 mol) was added dropwise during one hour to a solution containing 54.8 g (0.4 mol) of isonicotinic acid hydrazide (isoniazid) and 10 ml of glacial acetic acid in 400 ml of tertiary butyl alcohol. The resulting solution then was heated for 18 hours on a steam bath. Concentration of the reaction mixture to 100 ml yielded 13.0 g of unreacted isonicotinic acid hydrazide. The filtrate was concentrated to a thick syrup which was triturated with anhydrous ether and recrystallized from isopropyl alcohol; MP 87°C to 88.5°C. Elemental analysis of the product gave 1- isonicotinyl-2-(β-carbomethoxyethyl)hydrazine.
A slurry of 7.5 g (0.034 mol) of 1-isonicotinyl-2-(carbomethoxyethyl)- hydrazine and 5 ml of benzylamine is heated with stirring at 130°C for three hours. The cooled mass is then recrystallized from ethyl acetate to yield white needles melting at 151.1°C to 152.1°C.
Brand nameNialamid;Niamidal;Niamide;Niaquital;Niaquitil;Novazid;Nuredal;Psyco-retard;Surgexl.
Therapeutic FunctionAntidepressant
World Health Organization (WHO)Nialamide, a monoamine oxidase inhibitor (MAOI), was introduced in 1959 for the treatment of depressive illness. Subsequently concern regarding potentially serious interactions between MAOIs and foods containing tyramine inspired much restrictive regulatory action. However, MAOIs still retain a place in the treatment of serious depressive illness although there is no international consensus on which compounds should be preferred. Thus nialamide remains available in several countries.
General DescriptionNialamide is an antidepressant drug and its effect on β-adrenergic receptor-adenylate cyclase system of rat pineal gland has been studied. Antidepressant action of the combination of nialamide and 5-hydroxytryptophan has been evaluated.
HazardToxic in overdose.
Safety ProfilePoison by intravenous andintraperitoneal routes. Moderately toxic by ingestion.Mutation data reported. Experimental reproductiveeffects. An antidepressant. When heated to decompositionit emits toxic fumes of NOx.
NIALAMIDE Preparation Products And Raw materials
Raw materialsMethyl acrylate-->Isoniazid-->Benzylamine
Sodium thiocyanate Cyanuric acid Polyacrylamide 3-amino-N-benzyl-propanamide N-BENZYLACETAMIDE N-BENZYLFORMAMIDE NIALAMIDE Isoniazid 4-Pyridinemethaneamine PYRIDIN-4-YLMETHYL-HYDRAZINE Isonicotinamide 3-(Benzylamino)propylamine

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