imipramine imipramine imipramine, sold under the brand name tofranil, among others, is a tricyclic antidepressant (tca) mainly used in the treatment of depression. it is also effective in treating anxiety and panic disorder. imipramine may also be used off-label for nocturnal enuresis and chronic pain. imipramine is taken by mouth. imipramineclinical datatrade namestofranil, tofranil-pm, othersother namesmelipramine; g-22355ahfs/drugs.commonographmedlineplusa682389license data us dailymed: imipramine pregnancycategory au: c routes ofadministrationby mouth, intramuscular injectionatc coden06aa02 (who) legal statuslegal status au: s4 (prescription only) ca: ℞-only uk: pom (prescription only) us: ℞-only pharmacokinetic databioavailability94–96%protein binding86%metabolismliver (cyp1a2, cyp2c19, cyp2d6)metabolitesdesipramineelimination half-life20 hoursexcretionkidney (80%), fecal (20%)identifiers iupac name 3-(10,11-dihydro-5h-dibenzoazepin-5-yl)-n,n-dimethylpropan-1-amine cas number50-49-7 ypubchem cid3696iuphar/bps357drugbankdb00458 ychemspider3568 yuniiogg85sx4e4keggd08070 yas hcl: d00815 ychebichebi:47499 ychemblchembl11 ypdb ligandixx (pdbe, rcsb pdb)comptox dashboard (epa)dtxsid1043881 echa infocard100.000.039 chemical and physical dataformulac19h24n2molar mass280.415 g·mol−13d model (jsmol)interactive image smiles cn(c)cccn1c2ccccc2ccc2ccccc21 inchi inchi=1s/c19h24n2/c1-20(2)14-7-15-21-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)21/h3-6,8-11h,7,12-15h2,1-2h3 ykey:bcgwqeupmdmjnv-uhfffaoysa-n y (verify) common side effects of imipramine include dry mouth, drowsiness, dizziness, low blood pressure, rapid heart rate, urinary retention, and electrocardiogram changes. overdose of the medication can result in death. imipramine appears to work by increasing levels of serotonin and norepinephrine and by blocking certain serotonin, adrenergic, histamine, and cholinergic receptors. imipramine was discovered in 1951 and was introduced for medical use in 1957. it was the first tca to be marketed. imipramine and the other tcas have decreased in use in recent decades, due to the introduction of the selective serotonin reuptake inhibitors (ssris), which have fewer side effects and are far safer in overdose. medical uses imipramine is used in the treatment of depression and certain anxiety disorders. it is similar in efficacy to the antidepressant drug moclobemide. it has also been used to treat nocturnal enuresis because of its ability to shorten the time of delta wave stage sleep, where wetting occurs. in veterinary medicine, imipramine is used with xylazine to induce pharmacologic ejaculation in stallions. blood levels between 150 and 250 ng/ml of imipramine plus its metabolite desipramine generally correspond to antidepressant efficacy. available forms imipramine is available in the form of oral tablets and capsules. contraindications combining it with alcohol consumption causes excessive drowsiness. it may be unsafe during pregnancy. side effects these side effects can be contributed to the multiple receptors that imipramine targets such as serotonin, norepinephrine, dopamine, acetylcholine, epinephrine, histamine. those listed in italics below denote common side effects, separated by the organ systems that are affected. central nervous system: dizziness, drowsiness, confusion, seizures, headache, anxiety, tremors, stimulation, weakness, insomnia, nightmares, extrapyramidal symptoms in geriatric patients, increased psychiatric symptoms, paresthesia cardiovascular: orthostatic hypotension, ecg changes, tachycardia, hypertension, palpitations, dysrhythmias eyes, ears, nose and throat: blurred vision, tinnitus, mydriasis gastrointestinal: dry mouth, nausea, vomiting, paralytic ileus, increased appetite, cramps, epigastric distress, jaundice, hepatitis, stomatitis, constipation, taste change genitourinary: urinary retention hematological: agranulocytosis, thrombocytopenia, eosinophilia, leukopenia skin: rash, urticaria, diaphoresis, pruritus, photosensitivity overdose main articles: tricyclic antidepressant § overdose, and tricyclic antidepressant overdose interactions main article: tricyclic antidepressant § interactions pharmacology pharmacodynamics