N-benzyl-3-(pyridin-4-ylformohydrazido)propanamide

• ChemBase ID: 4364
• Molecular Formular: C16H18N4O2
• Molecular Mass: 298.33972
• Monoisotopic Mass: 298.14297584
• SMILES: O=C(NCc1ccccc1)CCNNC(=O)c1ccncc1
• Canonical SMILES: O=C(NCc1ccccc1)CCNNC(=O)c1ccncc1
• InChI: InChI=1S/C16H18N4O2/c21-15(18-12-13-4-2-1-3-5-13)8-11-19-20-16(22)14-6-9-17-10-7-14/h1-7,9-10,19H,8,11-12H2,(H,18,21)(H,20,22)
• InChIKey: NOIIUHRQUVNIDD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-benzyl-3-(pyridin-4-ylformohydrazido)propanamide
• IUPAC Traditional name: nialamide
• Brand Name: Delmoneurina; Espril; Isalizina; Mygal; NF-xIII; Nialamid; Niamid; Niamidal; Niamide; Niaquitil; Niazin; Novazid; Nuredal; Nyazin; Nyezin; Psicodisten; Surgex
• Synonyms: N-Benzyl-β-(isonicotinylhydrazino)propionamide; N-Isonicotinoyl-N′-[β-(N-benzylcarboxamido)ethyl]hydrazine; Nialamide; 1-(2-(Benzylcarbamoyl)ethyl)-2-isonicotinoylhydrazine; 1-[2-(Benzylcarbamoyl)ethyl]-2-isonicotinoylhydrazine; 2-(2-(Benzylcarbamoyl)ethyl)hydrazide isonicotinic acid; 2-(2-(Benzylcarbamoyl)ethyl)hydrazide, isonicotinic acid; 2-(2-(Benzylcarbamyl)ethyl)hydrazide isonicotinic acid; 2-[2-(Benzylcarbamoyl)ethyl]hydrazide isonicotinic acid; BEIH; Isonicitinic acid 2-[(2-benzylcarbamoyl)ethyl]hydrazide; Isonicotinic acid 2-((2-benzylcarbamoyl)ethyl)hydrazide; Isonicotinic acid, 2-(2-(benzylcarbamoyl)ethyl)hydrazide; Isonicotinic acid, 2-[2- (benzylcarbamoyl)ethyl]hydrazide; Isonicotinic acid, 2-[2-(benzylcarbamoyl)ethyl]hydrazide; Isonicotinic acid, 2-[2-(benzylcarbamoylethyl]hydrazide; Isonicotinic acid, {2-[2-(benzylcarbamoyl)ethyl]hydrazide}; Isonicotinic acid, {2-[2-(benzylcarbamoylethyl]hydrazide}; Lopac-N-1392; N-(2-(Benzylcarbamyl)ethylamino)isonicotinamide; N-Benzyl-3-(2-isonicotinoylhydrazino)propanamide; N-benzyl-beta-(isonicotinoylhydrazine)propionamide; N-benzyl-beta-(isonicotinylhydrazino)propionamide; N-isonicotinoyl-n'(beta-n-benzylcarboxamidoethyl)hydrazine; N-isonicotinyl hydrazide; Nialamida [inn-spanish]; Nialamidum [inn-latin]; Pyridine-4-carboxylic 2-[2-(benzylcarbamoyl)ethyl]hydrazide; Nialamide; N-异烟酰-N′-[β-(N-苄基甲酰氨基)乙基]肼; N-苄基-β-(异烟肼)丙酰胺; 吡啶-4-甲酰 2-[2-(苄基氨基甲酰)乙基]酰肼; 尼亚酰铵

Database IDs

• CAS Number: 51-12-7
• EC Number: 200-079-3
• MDL Number: MFCD00010106
• Beilstein Number: 492941
• PubChem SID: 24278185; 24855254; 46506047; 160967796
• PubChem CID: 4472
• ATC CODE: N06AF02
• Chemspider ID: 4317
• DrugBank ID: DB04820
• KEGG ID: D07337
• Unique Ingredient Identifier: T2Q0RYM725
• Wikipedia Title: Nialamide

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.652997
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 0.38634753
• LogD (pH = 7.4): 0.38957518
• Log P: 0.38961667
• Molar Refractivity: 93.9066 cm^3
• Polarizability: 31.85844 Å^3
• Polar Surface Area: 83.12 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.65
• LOG S: -3.53
• Solubility (Water): 8.73e-02 g/l

PROPERTIES

Physical Property

• Solubility: ethanol: soluble, clear to hazy
• Melting Point: 152-154 °C(lit.)
• Hydrophobicity(logP): 0.87 [HANSCH,C ET AL. (1995)]

Safety Information

• RTECS: NS1225000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-36/37/38-40
• Safety Statements: 22-26-36
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H315-H319-H332-H335-H351
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Pharmacology Properties

• Target: Others
• Admin Routes: Oral
• Legal Status: Uncontrolled
• Gene Information: human ... MAOA(4128), MAOB(4129)

Product Information

• Purity: 95%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C16H18N4O2

DETAILS

DrugBank - DB04820

• Drug Groups: withdrawn
• Description: Withdrawn from the Canadian, US, and UK markets in 1963 due to interactions with food products containing tyrosine.
• Affected Organisms: Humans and other mammals
• References: Benady DR, Clein LJ, Pare CM: Intramuscular nialamide in intractable depression. Dis Nerv Syst. 1965 Dec;26(12):792-4. [Pubmed] ; OULES J, CAZABON: [TREATMENT OF DEPRESSIVE STATES WITH INTRAVENOUS NIAMIDE.] Toulouse Med. 1964 Dec;65:1298-302. [Pubmed] ; VAISBERG M, McGAHEE CL, RADINGER N, SAUNDERS JC: Nialamide for the treatment of anergy and depression. Dis Nerv Syst. 1959 Aug;20(Suppl):22-5. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - N1392

Biochem/physiol Actions
非选择性 MAO-A/B 抑制剂。

Sigma Aldrich - 252999

Biochem/physiol Actions
Non-selective MAO-A/B inhibitor.
Packaging
1 g in glass bottle

REFERENCES

• Benady DR, Clein LJ, Pare CM: Intramuscular nialamide in intractable depression. Dis Nerv Syst. 1965 Dec;26(12):792-4. Pubmed
• OULES J, CAZABON: [TREATMENT OF DEPRESSIVE STATES WITH INTRAVENOUS NIAMIDE.] Toulouse Med. 1964 Dec;65:1298-302. Pubmed
• VAISBERG M, McGAHEE CL, RADINGER N, SAUNDERS JC: Nialamide for the treatment of anergy and depression. Dis Nerv Syst. 1959 Aug;20(Suppl):22-5. Pubmed