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Substance Name: Iproniazid [INN:BAN:DCF]
RN: 54-92-2
UNII: D892HFI3XA
InChIKey: NYMGNSNKLVNMIA-UHFFFAOYSA-N

Note

  • An irreversible inhibitor of monoamine oxidase types A and B that is used as an antidepressive agent. It has also been used as an antitubercular agent, but its use is limited by its toxicity.

Molecular Formula

  • C9-H13-N3-O

Molecular Weight

  • 179.2217
 

Classification Codes

  • Antidepressive Agents
  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Monoamine Oxidase Inhibitors
  • Mutation Data
  • Psychotropic Drugs
  • Reproductive Effect
  • Tumor Data
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Names and Synonyms

Name of Substance

  • Iproniazid
  • Iproniazid [INN:BAN:DCF]

MeSH Heading

  • Iproniazid

Synonyms

  • 1-Isonicotinoyl-2-isopropylhydrazine
  • 4-22-00-00551 (Beilstein Handbook Reference)
  • BRN 0142700
  • CCRIS 9177
  • EINECS 200-218-8
  • Euphozid
  • IPN
  • Iprazid
  • Iproniazid
  • Iproniazida
  • Iproniazida [INN-Spanish]
  • Iproniazide
  • Iproniazide [INN-French]
  • Iproniazidum
  • Iproniazidum [INN-Latin]
  • Iproniazyd
  • Iproniazyd [Polish]
  • Isonicotinic acid, N'-isopropyl hydrazide
  • Marsalid
  • Marsilid
  • N'-Isopropylisonicotinoylhydrazide
  • P 887
  • Rivivol
  • Ro 2-4572
  • UNII-D892HFI3XA
  • Yatrozide

Systematic Names

  • 4-Pyridinecarboxylic acid, 2-(1-methylethyl)hydrazide
  • Iproniazid
  • Isonicotinic acid 2-isopropylhydrazide

Registry Numbers

CAS Registry Number

  • 54-92-2

FDA UNII

  • D892HFI3XA

System Generated Number

  • 0000054922

Structure Descriptors

InChI

1S/C9H13N3O/c1-7(2)11-12-9(13)8-3-5-10-6-4-8/h3-7,11H,1-2H3,(H,12,13)

InChIKey

NYMGNSNKLVNMIA-UHFFFAOYSA-N

Smiles

CC(C)NNC(=O)c1ccncc1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral 95mg/kg (95mg/kg)   Annals of the New York Academy of Sciences. Vol. 80, Pg. 626, 1959.
human TDLo oral 2143ug/kg/D (2.143mg/kg) KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED

GASTROINTESTINAL: DECREASED MOTILITY OR CONSTIPATION
Acta Neurologia et Psychiatrica Belgica. Vol. 59, Pg. 977, 1959.
monkey LD50 oral 640mg/kg (640mg/kg)   Annals of the New York Academy of Sciences. Vol. 80, Pg. 626, 1959.
mouse LD50 intramuscular 615mg/kg (615mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD American Review of Tuberculosis. Vol. 65, Pg. 376, 1952.
mouse LD50 intraperitoneal 475mg/kg (475mg/kg) BEHAVIORAL: ANTICONVULSANT Japanese Journal of Pharmacology. Vol. 13, Pg. 186, 1963.
mouse LD50 intravenous 719mg/kg (719mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD American Review of Tuberculosis. Vol. 65, Pg. 376, 1952.
mouse LD50 oral 440mg/kg (440mg/kg)   Pharmaceutical Chemistry Journal Vol. 30, Pg. 750, 1996.
mouse LD50 subcutaneous 730mg/kg (730mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD American Review of Tuberculosis. Vol. 65, Pg. 376, 1952.
rabbit LD50 intravenous 117mg/kg (117mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD American Review of Tuberculosis. Vol. 65, Pg. 376, 1952.
rabbit LD50 oral 125mg/kg (125mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD American Review of Tuberculosis. Vol. 65, Pg. 376, 1952.
rabbit LDLo skin 2gm/kg (2000mg/kg)   Huntingdon Research Center Reports. Vol. -, Pg. -, 1972.
rat LD50 intraperitoneal 375mg/kg (375mg/kg) BEHAVIORAL: ANTICONVULSANT Japanese Journal of Pharmacology. Vol. 13, Pg. 186, 1963.
rat LD50 oral 365mg/kg (365mg/kg) BEHAVIORAL: TOXIC PSYCHOSIS Nature. Vol. 185, Pg. 532, 1960.
rat LD50 subcutaneous 538mg/kg (538mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 119, Pg. 444, 1957.
rat LD50 unreported 350mg/kg (350mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 363, 1970.
women LDLo oral 14mg/kg/2W-I (14mg/kg) LIVER: OTHER CHANGES Canadian Medical Association Journal. Vol. 78, Pg. 131, 1958.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 150 dec deg C   EXP
log P (octanol-water) 0.37 (none)   EXP
Water Solubility 2.68E+04 mg/L 25 EST
Vapor Pressure 1.36E-05 mm Hg 25 EST
Henry's Law Constant 4.68E-14 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 8.72E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.