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Substance Name: Nomifensine [INN:BAN]
RN: 24526-64-5
UNII: 1LGS5JRP31
InChIKey: XXPANQJNYNUNES-UHFFFAOYSA-N

Note

  • An isoquinoline derivative that prevents dopamine reuptake into synaptosomes. The maleate was formerly used in the treatment of depression. It was withdrawn worldwide in 1986 due to the risk of acute hemolytic anemia with intravascular hemolysis resulting from its use. In some cases, renal failure also developed. (From Martindale, The Extra Pharmacopoeia, 30th ed, p266)

Molecular Formula

  • C16-H18-N2

Molecular Weight

  • 238.332
 

Classification Codes

  • Dopamine Agents
  • Dopamine Uptake Inhibitors
  • Drug / Therapeutic Agent
  • Human Data
  • Membrane Transport Modulators
  • Neurotransmitter Agents
  • Neurotransmitter Uptake Inhibitors
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Nomifensine
  • Nomifensine [INN:BAN]

MeSH Heading

  • Nomifensine

Synonyms

  • (+-)-Nomifensin
  • (+-)-Nomifensine
  • 8-Amino-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline
  • CCRIS 9179
  • HSDB 7702
  • Linamiphen
  • Nomifensin
  • Nomifensina
  • Nomifensina [INN-Spanish]
  • Nomifensine
  • Nomifensinum
  • Nomifensinum [INN-Latin]
  • UNII-1LGS5JRP31

Systematic Names

  • 8-Isoquinolinamine, 1,2,3,4-tetrahydro-2-methyl-4-phenyl-
  • Isoquinoline, 1,2,3,4-tetrahydro-8-amino-2-methyl-4-phenyl-

Registry Numbers

CAS Registry Number

  • 24526-64-5

FDA UNII

  • 1LGS5JRP31

Other Registry Numbers

  • 118184-50-2
  • 89664-19-7

Related Registry Number

  • 32795-47-4 (maleate (1:1))

System Generated Number

  • 0024526645

Structure Descriptors

InChI

1S/C16H18N2/c1-18-10-14(12-6-3-2-4-7-12)13-8-5-9-16(17)15(13)11-18/h2-9,14H,10-11,17H2,1H3

InChIKey

XXPANQJNYNUNES-UHFFFAOYSA-N

Smiles

c12[C@@H](c3ccccc3)C[N@@](C)Cc1c(ccc2)N

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 intravenous 264mg/kg (264mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. Vol. 18, Pg. 1, 1979.
mammal (species unspecified) LD50 oral 300mg/kg (300mg/kg)   German Offenlegungsschrift Patent Document. Vol. #2901868,
mouse LD50 intraperitoneal 128mg/kg (128mg/kg)   Journal de Pharmacologie. Vol. 17, Pg. 37, 1986.
mouse LD50 intraperitoneal 141mg/kg (141mg/kg)   Journal of Medicinal Chemistry. Vol. 30, Pg. 798, 1987.
mouse LD50 oral 260mg/kg (260mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: AGGRESSION
Arzneimittel-Forschung. Drug Research. Vol. 32, Pg. 873, 1982.
mouse LD50 subcutaneous 269mg/kg (269mg/kg)   United States Patent Document. Vol. #4537895,
rat LD50 oral 267mg/kg (267mg/kg)   Journal of International Medical Research. Vol. 13, Pg. 77, 1985.
women TDLo oral 500ug/kg (0.5mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Human Toxicology. Vol. 6, Pg. 247, 1987.
women TDLo oral 7mg/kg/7D-I (7mg/kg) BLOOD: THROMBOCYTOPENIA

BLOOD: HEMORRHAGE
British Medical Journal. Vol. 288, Pg. 830, 1984.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 180 deg C   EXP
log P (octanol-water) 2.380 (none)   EST
Atmospheric OH Rate Constant 2.89E-10 cm3/molecule-sec 25 EST

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