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Imipramine hydrochloride

Chemical Name:
Imipramine hydrochloride
Molecular Formula:
Molecular Weight:
MDL Number:
MOL File:
MSDS File:
Modify Date:
2022-08-15 17:40:54

Imipramine hydrochloride Properties

Melting point 168-1700C
Flash point 9℃
storage temp. 2-8°C
solubility H2O: 50 mg/mL
form crystalline
color white
PH 4.2~5.2(100g/l,25℃)
Water Solubility Soluble in water
λmax 260nm(lit.)
Merck 14,4920
CAS DataBase Reference 113-52-0(CAS DataBase Reference)
EPA Substance Registry System 5H-Dibenz[b,f]azepine-5-propanamine, 10,11-dihydro-N,N-dimethyl-, monohydrochloride (113-52-0)

Pharmacokinetic data

Protein binding 95%
Excreted unchanged in urine 5%
Volume of distribution 31(L/kg)
Biological half-life 9-28 / -


Risk and Safety Statements

Signal word  Danger
Hazard statements  H300
Precautionary statements  P264-P270-P301+P310-P405-P501
Hazard Codes  Xn,T,F
Risk Statements  23/25-36/38-36/37/38-22-39/23/24/25-23/24/25-11
Safety Statements  7-16-24-33-45-36-26-36/37
RIDADR  UN 1230 3/PG 2
WGK Germany  3
RTECS  HO1925000
HS Code  2933995800
Toxicity LD50 in mice, rats (mg/kg): 400, 490 orally; 110, 90 i.p. (Tobe)

Imipramine hydrochloride price More Price(38)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich I-902 Imipramine hydrochloride solution 1.0?mg/mL in methanol (as free base), ampule of 1?mL, certified reference material, Cerilliant? 113-52-0 1mL $23.8 2022-05-15 Buy
Sigma-Aldrich I0899 Imipramine hydrochloride BioXtra, ≥99% (TLC) 113-52-0 5g $95.3 2022-05-15 Buy
Sigma-Aldrich BP932 Imipramine hydrochloride British Pharmacopoeia (BP) Reference Standard 113-52-0 50MG $210 2022-05-15 Buy
Sigma-Aldrich 1338007 Imipramine hydrochloride United States Pharmacopeia (USP) Reference Standard 113-52-0 200mg $400 2022-05-15 Buy
TCI Chemical I0971 Imipramine Hydrochloride >98.0%(HPLC) 113-52-0 1g $44 2022-04-27 Buy
Product number Packaging Price Buy
I-902 1mL $23.8 Buy
I0899 5g $95.3 Buy
BP932 50MG $210 Buy
1338007 200mg $400 Buy
I0971 1g $44 Buy

Imipramine hydrochloride Chemical Properties,Uses,Production

Chemical Properties

White Solid


Tofranil,Ciba Geigy,France,1959


Antidepressant;5-HT transport inhibitor


Tricyclic antidepressant; inhibits the serotonin and norepinephrine transporters. Has little effect on the dopamine transporter


Imipramine hydrochloride is used as a serotonin uptake inhibitor. It mainly used in the treatment of major depression and enuresis (inability to control urination). It has also been evaluated for use in panic disorder.

Manufacturing Process

20 parts of imino dibenzyl are dissolved in 100 parts by volume of absolutely dry benzene. A suspension of 4 parts NaNH2 in 50 parts by volume of absolute benzene are then added dropwise at 50° to 60°C after which the mixture is boiled for an hour under reflux. 13 parts of 3-dimethylamino n_x0002_propyl chloride are then added dropwise at 40° to 50°C and the mixture is boiled for 10 hours under reflux. After cooling, the benzene solution is thoroughly washed with water, whereupon the basic constituents are extracted with dilute hydrochloric acid.
The hydrochloric extract is then made alkaline and the separated base is extracted with ether. After drying, the solvent is evaporated and the residue is distilled in the high vacuum, whereby the N-(3-dimethylaminopropyl)-imino dibenzyl passes over at a temperature of 160°C under 0.1 mm pressure. The chlorohydrate with a melting point of 174° to 175°C is obtained therefrom with alcoholic hydrochloric acid.

brand name

Janimine (Abbott); Pramine (Alra); Presamine (Sanofi Aventis); Tofranil (Novartis); Tofranil (Tyco).

Therapeutic Function


General Description

Imipramine 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).

Biochem/physiol Actions

Tricyclic antidepressant; inhibits the serotonin and norepinephrine transporters with Kis of 7.7 nM and 67 nM, respectively. Has little effect on the dopamine transporter (Ki = 25 μM).

Clinical Use

The 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 Profile

Human 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 Treatments

In 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).

Drug interactions

Potentially hazardous interactions with other drugs
Alcohol: increased sedative effect.
Analgesics: increased risk of CNS toxicity with tramadol; possibly increased risk of side effects with nefopam; possibly increased sedative effects with opioids.
Anti-arrhythmics: increased risk of ventricular arrhythmias with amiodarone - avoid; increased risk of ventricular arrhythmias with disopyramide, flecainide or propafenone; avoid with dronedarone.
Antibacterials: increased risk of ventricular arrhythmias with delamanid, moxifloxacin and possibly telithromycin - avoid with delamanid and moxifloxacin.
Anticoagulants: may alter anticoagulant effect of coumarins.
Antidepressants: enhanced CNS excitation and hypertension with MAOIs and moclobemide - avoid; concentration possibly increased with SSRIs; risk of ventricular arrhythmias with citalopram and escitalopram - avoid; possible increased risk of convulsions with vortioxetine.
Antiepileptics: convulsive threshold lowered; concentration reduced by carbamazepine, phenobarbital and possibly fosphenytoin, phenytoin and primidone.
Antimalarials: avoid with artemether/lumefantrine and piperaquine with artenimol.
Antipsychotics: increased risk of ventricular arrhythmias especially with droperidol, fluphenazine, haloperidol, pimozide, sulpiride and zuclopenthixol - avoid; increased antimuscarinic effects with clozapine and phenothiazines; concentration increased by antipsychotics.
Antivirals: increased risk of ventricular arrhythmias with saquinavir - avoid; concentration possibly increased with ritonavir.
Atomoxetine: increased risk of ventricular arrhythmias and possibly convulsions.
Beta-blockers: increased risk of ventricular arrhythmias with sotalol; concentration increased by labetalol and propranolol
. Clonidine: tricyclics antagonise hypotensive effect; increased risk of hypertension on clonidine withdrawal.
Dapoxetine: possibly increased risk of serotonergic effects - avoid. Dopaminergics: avoid use with entacapone; CNS toxicity reported with selegiline and rasagiline.
Pentamidine: increased risk of ventricular arrhythmias.
Sympathomimetics: increased risk of hypertension and arrhythmias with adrenaline and noradrenaline; metabolism possibly inhibited by methylphenidate.


Imipramine is extensively demethylated by first-pass metabolism in the liver, to its primary active metabolite, desipramine (desmethylimipramine). Paths of metabolism of both imipramine and desipramine include hydroxylation and N-oxidation.
About 80% is excreted in the urine and about 20% in the faeces, mainly in the form of inactive metabolites. Urinary excretion of unchanged imipramine and of the active metabolite desipramine is about 5% and 6% respectively. Only small quantities of these are excreted in the faeces.

Imipramine hydrochloride Preparation Products And Raw materials

Raw materials




Preparation Products

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View Lastest Price from Imipramine hydrochloride manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
2019-07-06 Imipramine hydrochloride
US $1.00 / KG 1G 98% 100KG Career Henan Chemical Co
Imipramine hydrochloride,10,11-Dihydro-N,N-dimethyl-5H-dibenz[b,f]azepine-5-propanamine hydrochloride, 5-[3-(Dimethylamino)propyl]-10,11-dihydro-5H-dibenz[b,f]azepine hydrochloride Imipramine Hydrochloride (200 mg) Methanol(test Imipramine HCl, 1.0 mg/mL as free base) 10,11-Dihydro-N,N-dimithyl-5,H-dibenz[b,f]azepine-5-propanamine 5-(3-dimethylaminopropyl)-10,11-dihydro-5h-dibenz(b,f)azepinehydrochloride tofranil tofranile LABOTEST-BB LT00452014 IMIPRAMINE HCL IMIPRAMINE HYDROCHLORIDE Imipramine hydrochloride solution 10,11-DIHYDRO-N,N-DIMETHYL-5H-DIBENZ[B,F]AZEPINE-5-PROPANAMINE HYDROCHLORIDE 10,11-DIHYDRO-N,N-DIMETHYL-DIBENZ[B,F]AZEPINE-5-PROPANAMINE HYDROCHLORIDE 10,11-dihydro-5-(3-(dimethylamino)propyl)-5h-dibenz[b,f]azepine hydrochloride Imipramin hydrochloride 5H-dibenz[b,f]azepine,5-[3-(dimethylamino)propyl]-10,11-dihydro-,monohydrochloride antideprinhydrochloride chimoreptin chrytemin cocapimipramine25 deprinol dynazina efuranol f)azepine,10,11-dihydro-5-(3-(dimethylamino)propyl)-5h-dibenz(hydrochlor f)azepine,5-(3-(dimethylamino)propyl)-10,11-dihydro-5h-dibenz(monohydrochl f)azepine,5-(3-(dimethylamino)propyl)-10,11-dihydro-5h-dibenz(monohydrochloride f)azepine-5-propanamine,10,11-dihydro-n,n-dimethyl-5h-dibenz(monohydroch f]azepine-5-propanamine,10,11-dihydro-n,n-dimethyl-5h-dibenz[monohydrochlo feinalmin fujisawa g22355 ia-pram imavate imidol imilanyle imipraminemonohydrochloride iprogen janimine melipraminehydrochloride n-(3-dimethylaminopropyl)iminodibenzylhydrochloride n-(gamma-dimethylaminopropyl)iminodibenzylhydrochloride n-(gamma-dimetilaminopropil)-iminodibenzilecloridrato N-(γ-dimethylaminopropyl)iminodibenzylhydrochloride nsc114900 persamine pertofram presamine pryleugan sk-praminehydrochloride teperine IMIPRAMINE HYDROCHLORIDE SIGMAULTRA IMIPRAMINE HYDROCHLORIDE METHANOL*SOLUTI ON CAFFEINE EPC(CRM STANDARD) Imipramine-2,4,6,8-D4HCI 5H-Dibenzb,fazepine-5-propanamine, 10,11-dihydro-N,N-dimethyl-, monohydrochloride IMIPRAMINEHYDROCHLORIDE,USP 5-[3-(Dimethylamino)propyl]-10,11-dihydro-5H-dibenz[b,f]azepine hydrochloride, 10,11-Dihydro-N,N-dimethyl-5H-dibenz[b,f]azepine-5-propanamine hydrochloride Imipramine-2,4,6,8-D4CI