Compound: Nialamide
SMILES: O=C(NNCCC(=O)NCc1ccccc1)c2ccncc2
InChIKey: NOIIUHRQUVNIDD-UHFFFAOYSA-N
Synonyms: Nialamide, 51-12-7, Niamid, Nialamid, Niaquitil, Niamidal, Nuredal, Niazin, Nyazin, BEIH, Psicodisten, Espril, Novazid, Mygal, Delmoneurina, Isalizina, Nialamida, Delmoneurinaesprilisalizina, Nialamidum, N-(2-(Benzylcarbamyl)ethylamino)isonicotinamide, N-Benzyl-beta-(isonicotinylhydrazino)propionamide, 2-(2-(Benzylcarbamyl)ethyl)hydrazide isonicotinic acid, 2-(2-(Benzylcarbamoyl)ethyl)hydrazide isonicotinic acid, DTXSID1023362, P 1133, N-Benzyl-beta-(isonicotinoylhydrazine)propionamide, 1-(2-(Benzylcarbamoyl)ethyl)-2-isonicotinoylhydrazine, Isonicotinic acid 2-((2-benzylcarbamoyl)ethyl)hydrazide, Isonicotinic acid, 2-(2-(benzylcarbamoyl)ethyl)hydrazide, N-Isonicotinoyl-N'(beta-N-benzylcarboxamidoethyl)hydrazine, NSC-124514, T2Q0RYM725, NSC124514, 4-Pyridinecarboxylic acid, 2-(3-oxo-3-((phenylmethyl)amino)propyl)hydrazide, 4-Pyridinecarboxylic acid, 2-[3-oxo-3-[(phenylmethyl)amino]propyl]hydrazide, DTXCID503362, N(sup1)-beta-Benzylcarbamoylethyl-N(sup2)-isonicotinoylhydrazine, 4-Pyridinecarboxylic acid 2-(3-oxo-3-((phenylmethyl)amino)propyl)hydrazide, 1-[2-(Benzylcarbamoyl)ethyl]-2-isonicotinoylhydrazine, Isonicotinic acid, 2-[2-(benzylcarbamoyl)ethyl]hydrazide, 2-[2-(Benzylcarbamoyl)ethyl]hydrazide isonicotinic acid, 4-Pyridinecarboxylic acid 2-[3-oxo-3-[(phenylmethyl)amino]propyl]hydrazide, RefChem:853812, N06AF02, N-benzyl-3-(pyridin-4-ylformohydrazido)propanamide, 200-079-3, N-benzyl-3-[2-(pyridine-4-carbonyl)hydrazinyl]propanamide, NSC 124514, MLS000069474, Nialamide (INN), N-Benzyl-3-(2-isonicotinoylhydrazineyl)propanamide, N-benzyl-3-[(pyridin-4-yl)formohydrazido]propanamide, CAS-51-12-7, NCGC00015726-06, SMR000059131, NIALAMIDE [INN], Nialamidum [INN-Latin], Nialamida [INN-Spanish], N-Benzyl-.beta.-(isonicotinylhydrazino)propionamide, N-Benzyl-.beta.-(isonicotinoylhydrazine)propionamide, N-benzyl-3-[2-(pyridine-4-carbonyl)hydrazino]propanamide, N-Isonicotinoyl-N'-(.beta.-N-benzylcarboxamidoethyl)hydrazine, Nyezin, CCRIS 3512, N-Isonicotinyl hydrazide, SR-01000000028, EINECS 200-079-3, Lopac-N-1392, N-Benzyl-3-(2-isonicotinoylhydrazino)propanamide, Nialamide [INN:BAN:NF], BRN 0492941, UNII-T2Q0RYM725, HSDB 7698, Nialamide, 95%, Niamid (TN), NIALAMIDE [MI], NIALAMIDE [HSDB], N(sup 1)-beta-Benzylcarbamoylethyl-N(sup 2)-isonicotinoylhydrazine, Opera_ID_1336, Prestwick0_001099, Prestwick1_001099, Prestwick2_001099, Prestwick3_001099, CBChromo1_000220, NIALAMIDE [MART.], NIALAMIDE [WHO-DD], Nucleic Acid Electrophoresis, Lopac0_000865, SCHEMBL49430, BSPBio_001178, 5-22-02-00251 (Beilstein Handbook Reference), MLS001076132, MLS001424258, SPBio_003059, WLN: T6NJ DVMM2VM1R, BPBio1_001296, orb1308574, CHEMBL1256841, Isonicitinic acid 2-[(2-benzylcarbamoyl)ethyl]hydrazide, Isonicotinic acid, 2-[2-(benzylcarbamoylethyl]hydrazide, CHEBI:94510, BDBM163693, HMS1571K20, HMS2052O21, HMS2089M13, HMS2093L10, HMS2098K20, HMS2233A06, HMS3262N11, HMS3372J15, HMS3394O21, HMS3715K20, HMS6018C19, Pharmakon1600-01505986, HY-B1199, Tox21_110208, Tox21_500865, EBC-26514, MFCD00010106, MSK167747, NSC759298, AKOS003390166, Tox21_110208_1, CCG-101150, CS-4827, DB04820, LP00865, NC00400, NSC-759298, SDCCGSBI-0050840.P003, NCGC00015726-01, NCGC00015726-02, NCGC00015726-03, NCGC00015726-04, NCGC00015726-05, NCGC00015726-07, NCGC00015726-08, NCGC00015726-09, NCGC00015726-11, NCGC00015726-16, NCGC00022832-03, NCGC00022832-04, NCGC00261550-01, MS-24288, SBI-0050840.P002, DB-051905, AB00384282, EU-0100865, NS00003489, ST45022574, SW197230-4, D07337, F85257, N 1392, AB00384282-14, AB00384282_15, AB00384282_16, EN300-12579134, N-Benzyl-3-(2-isonicotinoylhydrazino)propanamide #, Q2359711, SR-01000000028-2, SR-01000000028-5, SR-01000000028-7, SR-01000000028-8, BRD-K12102668-001-04-0, BRD-K12102668-001-24-8, BRD-K12102668-001-25-5, N-benzyl-3-[(4-pyridylcarbonylamino)amino]propanamide, N1-.beta.-Benzylcarbamoylethyl-N2-isonicotinoylhydrazine, N-Benzyl-3-[2-(pyridine-4-carbonyl)hydrazin-1-yl]propanamide, 3-[[oxo(pyridin-4-yl)methyl]hydrazo]-N-(phenylmethyl)propanamide, Hydrazine, N-isonicotinoyl-N'-[beta-(N-benzylcarboxamido)ethyl]-, n(sup1)-.beta.-Benzylcarbamoylethyl-n(sup2)isonicotinoylhydrazine, N-(phenylmethyl)-3-[2-(pyridin-4-ylcarbonyl)hydrazino]propanamide, N-Benzyl-3-[N'-(1-pyridin-4-yl-methanoyl)-hydrazino]-propionamide
Theoretical properties:
molecular_formula: C16H18N4O2
molecular_weight: 298.34 g/mol
exact_mass: 298.14297583 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 3
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 7
heavy_atom_count: 22
topological_polar_surface_area: 83.1 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: White crystalline powder
color: White crystalline powder
solubility: Freely soluble in acidic solvents
Descriptions:
pubchem: 3-[[oxo(pyridin-4-yl)methyl]hydrazo]-N-(phenylmethyl)propanamide is an organonitrogen compound and an organooxygen compound. It is functionally related to a beta-amino acid.
chembl: NIALAMIDE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Nialamide (Niamid, Niamide, Nuredal, Surgex) is a non-selective, irreversible monoamine oxidase inhibitor (MAOI) of the hydrazine class that was used as an antidepressant. It was withdrawn by Pfizer several decades ago due to the risk of hepatotoxicity.
Side effects include agitation and insomnia, less frequently dry mouth, dizziness, blurred vision, and hypomania, and rarely leukopenia and hepatitis. As with other MAOIs, a hypertensive crisis can be triggered by co-ingestion of tyramine. It is metabolized into isoniazid, an anti-tuberculosis agent, and so is contraindicated in patients with tuberculosis. The recommended dosage range is 75 to 200 mg per day, with maintenance doses as low as 12.5 mg every other day.
The antiatherogenic activity of nialamide was used to design pyridinolcarbamate.