- Product Name:
- Clomipramine hydrochloride
- CHLOROIMIPRAMINE HYDROCHLORIDE
- CHLORIMIPRAMINE HYDROCHLORIDE
- CLOMIPRAMINE HCL
- CLOMIPRAMINE HYDROCHLORIDE
- 3-chloro-5-[3-(dimethylamino)propyl]-10,11-dihydro-5h-dibenz[b,f]azepine monohydrochloride
- 3-CHLORO-10,11-DIHYDRO-N,N-DIMETHYL-5H-DIBENZ[B,F]AZEPINE-5-PROPANAMINE HYDROCHLORIDE
- Product Categories:
- Other APIs
- Intermediates & Fine Chemicals
- Serotonin receptor
- Chemical Amines
- Mol File:
Clomipramine hydrochloride Chemical Properties
- Melting point:
- Flash point:
- storage temp.
- H2O: 25 mg/mL
- white to off-white
- CAS DataBase Reference
- 17321-77-6(CAS DataBase Reference)
- Hazard Codes
- Risk Statements
- Safety Statements
- WGK Germany
- HS Code
- Language:English Provider:SigmaAldrich
Clomipramine hydrochloride Usage And Synthesis
Clomipramine is a tricyclic antidepressant, the 3-
Potent, selective 5-HT uptake blocker
Serotonin reuptake inhibitor. Antidepressant; antiobsessional agent
anti-depressant, serotonin uptake inhibitor
ChEBI: A hydrochloride resulting from the reaction of equimolar amounts of clomipramine and hydrogen chloride. One of the more sedating tricyclic antidepressants, it is used for the treatment of depression as well as obsessive-compulsive disorder and phobias.
22.9 parts of 3-chloroiminodibenzyl are dissolved in 300 parts by volume of xylene, and 4 parts of sodium amide, pulverized and suspended in toluene,are added thereto while stirring and maintaining the whole under a nitrogen atmosphere. The xylene solution immediately turns dark colored, but upon crystallization of the sodium salt therefrom it becomes again light-colored. The reaction mixture is stirred for about 2 hours at 80°C until the development of ammonia has terminated. A solution of γ-dimethylaminopropyl chloride in toluene, prepared by setting free a corresponding amount of the free base from 17.4 parts of its hydrochloride salt by addition of aqueous sodium hydroxide solution in about 10% excess, extraction with toluene and drying for 2 hours over anhydrous sodium sulfate is added to the xylene solution containing the sodium salt mentioned above and the whole is stirred under reflux for 15 hours. Precipitated sodium chloride is filtered off and the filtrate is concentrated. The residue is diluted with ether, and the hydrochloride of 3- chloro-5-(γ-dimethylaminopropyl)-iminodibenzyl is precipitated by introducing dry, gaseous hydrogen chloride. It is filtered off under suction and purified by repeated recrystallization from acetone; the pure substance melts at 191.5°C to 192°C.
Clomipramine (Anafranil) is up to 50 times as potentas imipramine in some bioassays. This does not implyclinical superiority, but it might be informative about tricyclicand, possibly, other reuptake inhibitors. The chloro replacingthe H-substituent could increase potency by increasingdistribution to the CNS, but it is unlikely that this wouldgive the potency magnitude seen. It might be conjecturedthat an H-bond between the protonated amino group (as invivo) and the unshared electrons of the chloro substituent might stabilize a β-arylamine–like shape and give moreefficient competition for the transporter. The drug is anantidepressant. It is used in obsessive–compulsive disorder,an anxiety disorder that may have an element of depression.
Potent, selective 5-HT uptake blocker. Antidepressant. Binds to the human 5-HT transporter with a K i of 0.05 nmol/l. Also available as part of the Serotonin Uptake Inhibitor Tocriset™ .
Veterinary Drugs and Treatments
In veterinary medicine, clomipramine is used primarily in dogs as
a treatment for obsessive-compulsive disorders (ritualistic stereotypical
behaviors) and may be useful for dominance
Clomipramine may also be useful in cats, particularly for behaviors such as urine spraying. One prospective, double-blinded controlled study in cats with psychogenic alopecia comparing clomipramine (0.5 mg/kg PO daily) versus placebo showed no statistic differences in study parameters (Mertens, Torres et al. 2006).
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 and moxifloxacin and possibly telithromycin - avoid with delamanid and moxifloxacin.
Anticoagulants: may alter anticoagulant effect of coumarins.
Antidepressants: possibly increased serotonergic effects with duloxetine; enhanced CNS excitation and hypertension with MAOIs and moclobemide; 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 risk of ventricular arrhythmias with risperidone; 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.
Clonidine: tricyclics antagonise hypotensive effect; increased risk of hypertension on clonidine withdrawal.
Cytotoxics: increased risk of ventricular arrhythmias with arsenic trioxide.
Dapoxetine: possibly increased risk of serotonergic effects - avoid.
Dopaminergics: avoid use with entacapone; CNS toxicity reported with selegiline and rasagiline.
Methylthioninium: risk of CNS toxicity - avoid if possible.
Clomipramine is extensively demethylated during
first-pass metabolism in the liver to its primary active
metabolite, desmethylclomipramine. Clomipramine has
been estimated to have a plasma elimination half-life of
about 21 hours; that of desmethylclomipramine is longer
(about 36 hours).
Paths of metabolism of both clomipramine and desmethylclomipramine include hydroxylation and N-oxidation. About two-thirds of a single dose of clomipramine is excreted in the urine, mainly in the form of its metabolites, either free or in conjugated form; the remainder of the dose appears in the faeces.
Clomipramine hydrochloride Preparation Products And Raw materials
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