Skip Navigation
ChemIDplus A TOXNET DATABASE LiteBrowseAdvanced

Substance Name: Nomifensine maleate [USAN]
RN: 32795-47-4
UNII: 76S8CUH5MR
InChIKey: GEOCVSMCLVIOEV-BTJKTKAUSA-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 It was withdrawn worldwide in 1986 due to the risk of acute hemolytic anemia with intravascular hemolysis resulting from its use.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.C4-H4-O4

Molecular Weight

  • 354.404
 

Classification Codes

  • Antidepressant
  • Drug / Therapeutic Agent
  • Human Data
  • Reproductive Effect
* denotes mobile formatted website

Links to Resources


Search for this InChIKey on the Web

Names and Synonyms

Name of Substance

  • Nomifensine maleate [USAN]

Synonyms

  • (+-)-Nomifensine hydrogen maleate
  • 8-Amino-1,2,3,4-tetrahydro-2-methyl-4-phenylisoquinoline maleate (1:1)
  • 8-Amino-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline maleate
  • Alival
  • Alival (antidepressant)
  • CCRIS 1914
  • EINECS 251-223-7
  • HOE 984
  • Hostalival
  • Merital
  • Merital AM
  • Nomifensine hydrogen maleate
  • Nomifensine maleate
  • NSC 289114
  • Psicronizer
  • UNII-76S8CUH5MR

Systematic Names

  • 8-Ammonio-1,2,3,4-tetrahydro-2-methyl-4-phenylisoquinolinium maleate
  • 8-Isoquinolinamine, 1,2,3,4-tetrahydro-2-methyl-4-phenyl-, (Z)-2-butenedioate (1:1)

Registry Numbers

CAS Registry Number

  • 32795-47-4

FDA UNII

  • 76S8CUH5MR

Other Registry Number

  • 98644-14-5

Related Registry Number

  • 24526-64-5 (Parent)

System Generated Number

  • 0032795474

Molecular Formulas

Molecular Formula

  • C16-H18-N2.C4-H4-O4

Molecular Formula Fragments

  • C16-H18-N2
  • C4-H4-O4
  • COMPONENT

Structure Descriptors

InChI

1S/C16H18N2.C4H4O4/c1-18-10-14(12-6-3-2-4-7-12)13-8-5-9-16(17)15(13)11-18;5-3(6)1-2-4(7)8/h2-9,14H,10-11,17H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1-

InChIKey

GEOCVSMCLVIOEV-BTJKTKAUSA-N

Smiles

c12[C@@H](c3ccccc3)C[N@@H+](C)Cc1c(N)ccc2.C(=C/C(=O)[O-])\C(O)=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo intravenous 1429ug/kg/20M (1.429mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION

ENDOCRINE: OTHER CHANGES

CARDIAC: CHANGE IN RATE
Clinical Pharmacology and Therapeutics Vol. 41, Pg. 88, 1987.
man TDLo oral 66429ug/kg/31 (66.429mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) Canadian Medical Association Journal. Vol. 133, Pg. 207, 1985.
mouse LD50 intraperitoneal 140mg/kg (140mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA
Oyo Yakuri. Pharmacometrics. Vol. 27, Pg. 1019, 1984.
mouse LD50 intravenous 68mg/kg (68mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Oyo Yakuri. Pharmacometrics. Vol. 27, Pg. 1019, 1984.
mouse LD50 oral 300mg/kg (300mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Oyo Yakuri. Pharmacometrics. Vol. 27, Pg. 1019, 1984.
mouse LD50 subcutaneous 195mg/kg (195mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Oyo Yakuri. Pharmacometrics. Vol. 27, Pg. 1019, 1984.
rabbit LD50 intravenous > 32mg/kg (32mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: EXCITEMENT
Arzneimittel-Forschung. Drug Research. Vol. 23, Pg. 45, 1973.
rabbit LD50 oral 854mg/kg (854mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: TREMOR

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Arzneimittel-Forschung. Drug Research. Vol. 23, Pg. 45, 1973.
rat LD50 intraperitoneal 112mg/kg (112mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 27, Pg. 1019, 1984.
rat LD50 intraperitoneal 112mg/kg (112mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA
Oyo Yakuri. Pharmacometrics. Vol. 27, Pg. 1019, 1984.
rat LD50 intravenous 66mg/kg (66mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 27, Pg. 1019, 1984.
rat LD50 intravenous 66mg/kg (66mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Oyo Yakuri. Pharmacometrics. Vol. 27, Pg. 1019, 1984.
rat LD50 oral 430mg/kg (430mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: TREMOR
Arzneimittel-Forschung. Drug Research. Vol. 23, Pg. 45, 1973.
rat LD50 subcutaneous 193mg/kg (193mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Oyo Yakuri. Pharmacometrics. Vol. 27, Pg. 1019, 1984.