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Substance Name: Clomipramine [INN:BAN]
RN: 303-49-1
UNII: NUV44L116D
InChIKey: GDLIGKIOYRNHDA-UHFFFAOYSA-N

Note

  • A tricyclic antidepressant similar to IMIPRAMINE that selectively inhibits the uptake of serotonin in the brain. It is readily absorbed from the gastrointestinal tract and demethylated in the liver to form its primary active metabolite, desmethylclomipramine.

Molecular Formula

  • C19-H23-Cl-N2

Molecular Weight

  • 314.8577
 

Classification Codes

  • Antidepressive Agents
  • Antidepressive Agents, Tricyclic
  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Membrane Transport Modulators
  • Neurotransmitter Agents
  • Neurotransmitter Uptake Inhibitors
  • Psychotropic Drugs
  • Reproductive Effect
  • Serotonin Agents
  • Serotonin Uptake Inhibitors

Names and Synonyms

Name of Substance

  • Clomipramine
  • Clomipramine [INN:BAN]

MeSH Heading

  • Clomipramine

Synonyms

  • 3-Chloro-5-(3-(dimethylamino)propyl)-10,11-dihydro-5H-dibenz(b,f)azepine
  • 3-Chloroimipramine
  • 5-20-08-00103 (Beilstein Handbook Reference)
  • 5H-Dibenz(b,f)azepine, 3-chloro-5-(3-(dimethylamino)propyl)-10,11-dihydro-
  • Anafranil (free base)
  • Anafranil base
  • BRN 1323477
  • Chlorimipramine
  • Clomicalm
  • Clomipramina
  • Clomipramina [INN-Spanish]
  • Clomipramine
  • Clomipraminum
  • Clomipraminum [INN-Latin]
  • EINECS 206-144-2
  • HSDB 7746
  • Monochlorimipramine
  • NSC 169865
  • UNII-NUV44L116D

Systematic Names

  • 5H-Dibenz(b,f)azepine, 10,11-dihydro-3-chloro-5-(3-(dimethylamino)propyl)-
  • 5H-Dibenz(b,f)azepine, 3-chloro-5-(3-(dimethylamino)propyl)-10,11-dihydro- (8CI)
  • 5H-Dibenz(b,f)azepine-5-propanamine, 3-chloro-10,11-dihydro-N,N-dimethyl-
  • Clomipramine

Registry Numbers

CAS Registry Number

  • 303-49-1

FDA UNII

  • NUV44L116D

Other Registry Number

  • 83162-38-3

Related Registry Number

  • 17321-77-6 (mono-hydrochloride)

System Generated Number

  • 0000303491

Structure Descriptors

InChI

1S/C19H23ClN2/c1-21(2)12-5-13-22-18-7-4-3-6-15(18)8-9-16-10-11-17(20)14-19(16)22/h3-4,6-7,10-11,14H,5,8-9,12-13H2,1-2H3

InChIKey

GDLIGKIOYRNHDA-UHFFFAOYSA-N

Smiles

N1(CCCN(C)C)c2c(CCc3ccccc13)ccc(c2)Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 357ug/kg (0.357mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Journal of Clinical Pyschopharmacology. Vol. 2, Pg. 215, 1982.
mouse LD50 intraperitoneal 150mg/kg (150mg/kg)   Journal of Medicinal Chemistry. Vol. 21, Pg. 448, 1978.
mouse LD50 intravenous 27mg/kg (27mg/kg)   Acta Pharmaceutica Suecica. Vol. 13, Pg. 485, 1976.
mouse LD50 oral 380mg/kg (380mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: WAKEFULNESS
German Offenlegungsschrift Patent Document. Vol. #2618152,
rat LD50 intraperitoneal 149mg/kg (149mg/kg)   Toxicology. Vol. 24, Pg. 335, 1982.
rat LD50 oral 613mg/kg (613mg/kg)   Toxicology. Vol. 24, Pg. 335, 1982.
women TDLo intravenous 3400ug/kg/47M (3.4mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION
British Medical Journal. Vol. 3, Pg. 698, 1972.
women TDLo oral 10mg/kg/5D-I (10mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION British Medical Journal. Vol. 1, Pg. 406, 1971.
women TDLo oral 30mg/kg (30mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF ENDOCRINE PANCREAS

BEHAVIORAL: COMA

GASTROINTESTINAL: DECREASED MOTILITY OR CONSTIPATION
Journal of Toxicology, Clinical Toxicology. Vol. 32, Pg. 425, 1994.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 189.5 deg C   EXP
log P (octanol-water) 5.19 (none)   EXP
Water Solubility 0.294 mg/L 25 EST
Vapor Pressure 4.07E-07 mm Hg 25 EST
Henry's Law Constant 7.48E-09 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.94E-10 cm3/molecule-sec 25 EST

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