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Imipramine hydrochloride

Basic information Safety Related Supplier
Imipramine hydrochloride Basic information
Imipramine hydrochloride Chemical Properties
Safety Information
Imipramine hydrochloride Usage And Synthesis
  • Chemical PropertiesWhite Solid
  • UsesTricyclic antidepressant; inhibits the serotonin and norepinephrine transporters. Has little effect on the dopamine transporter
  • UsesAntidepressant;5-HT transport inhibitor
  • brand nameJanimine (Abbott); Pramine (Alra); Presamine (Sanofi Aventis); Tofranil (Novartis); Tofranil (Tyco).
  • General DescriptionImipramine hydrochloride, 5-[3-(dimethylamino)propyl]-10,11-dihydro-5H-dibenz[b,f]azepine monohydrochloride(Tofranil), is the lead compound of the TCAs. It is also a closerelative of the antipsychotic phenothiazines (replace the10–11 bridge with sulfur, and the compound is the antipsychoticagent promazine). It has weaker D2 postsynaptic blockingactivity than promazine and mainly affects amines (5-HT,NE, and DA) via the transporters. As is typical of dimethylaminocompounds, anticholinergic and sedative (central H1block) effects tend to be marked. The compound per se has a tendency toward a high 5-HT-to-NE uptake block ratio andprobably can be called a serotonin transport inhibitor(SERTI). Metabolic inactivation proceeds mainly by oxidativehydroxylation in the 2-position, followed by conjugationwith glucuronic acid of the conjugate. Urinary excretion predominates(about 75%), but some biliary excretion (up to25%) can occur, probably because of the large nonpolargrouping. Oxidative hydroxylation is not as rapid or completeas that of the more nucleophilic ring phenothiazine antipsychotics;consequently, appreciable N-demethylation occurs,with a buildup of norimipramine (or desimipramine).
  • Clinical UseThe demethylated metabolite is less anticholinergic, lesssedative, and more stimulatory and is a SNERI.Consequently, a patient treated with imipramine has twocompounds that contribute to activity. Overall, the effect isnonselective 5-HT versus NE reuptake.
  • Safety ProfileHuman poison by ingestion. An experimental poison by ingestion, intravenous, subcutaneous, and intraperitoneal routes. An experimental teratogen. Human systemic effects by ingestion: sleep, somnolence, convulsions, muscle contraction or spasticity, coma, blood pressure decrease, dyspnea (difficulty in breathing), paresthesia (abnormal sensations), and kidney changes. Experimental reproductive effects. Mutation data reported. Used in the treatment of depression. When heated to decomposition it emits very toxic fumes of NO, and HCl. See also DIAZEPAM.
  • Veterinary Drugs and TreatmentsIn dogs and cats, imipramine has been used to treat cataplexy and urinary incontinence. In horses, imipramine has been used to treat narcolepsy and ejaculatory dysfunction (no parenteral dosage forms available).
Imipramine hydrochloride Preparation Products And Raw materials
Imipramine hydrochloride(113-52-0)Related Product Information
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