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Clomipramine hydrochloride

Product Name
Clomipramine hydrochloride
CAS No.
17321-77-6
Chemical Name
Clomipramine hydrochloride
Synonyms
ANAFRANIL;Clomicalm;anaphranil;Chlomipramine;CLOMIPRAMINE HCL;Clomipramine hydroch;Chloroimipram-ine HCl;ANAFRANIL HYDROCHLORIDE;Clomipraminhydrochlorid;Clomipramine-13C-d3 HCl
CBNumber
CB2173106
Molecular Formula
C19H24Cl2N2
Formula Weight
351.31
MOL File
17321-77-6.mol
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Clomipramine hydrochloride Property

Melting point:
189-190°C
Flash point:
9℃
storage temp. 
2-8°C
solubility 
H2O: 25 mg/mL
form 
powder
color 
white to off-white
PH
3.5～5.0（100g/l，25℃）
BCS Class
3/1
InChIKey
WIMWMKZEIBHDTH-UHFFFAOYSA-N
CAS DataBase Reference
17321-77-6(CAS DataBase Reference)
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Safety

Hazard Codes 
Xn,T,F
Risk Statements 
20/21/22-39/23/24/25-23/24/25-11-36/37/38
Safety Statements 
36-45-36/37-16-7-62-38-36/37/39-28-26-24/25-22-20/21-13
RIDADR 
3249
WGK Germany 
3
RTECS 
HN9055000
HazardClass 
6.1(b)
PackingGroup 
III
HS Code 
2933996100
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H302Harmful if swallowed

H336May cause drowsiness or dizziness

H370Causes damage to organs

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P273Avoid release to the environment.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
C-118
Product name
Clomipramine hydrochloride solution
Purity
1.0?mg/mL in methanol (as free base), ampule of 1?mL, certified reference material, Cerilliant?
Packaging
1mL
Price
$26.6
Updated
2024/03/01
Sigma-Aldrich
Product number
1140247
Product name
Clomipramine hydrochloride
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$436
Updated
2024/03/01
Sigma-Aldrich
Product number
BP980
Product name
Clomipramine hydrochloride
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
100MG
Price
$252
Updated
2023/06/20
Alfa Aesar
Product number
J62485
Product name
Clomipramine hydrochloride
Packaging
1g
Price
$31.65
Updated
2024/03/01
Alfa Aesar
Product number
J62485
Product name
Clomipramine hydrochloride
Packaging
5g
Price
$105.65
Updated
2024/03/01
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Clomipramine hydrochloride Chemical Properties,Usage,Production

Description

Clomipramine is a tricyclic antidepressant, the 3-chlorinated derivative of imipramine . Like imipramine, clomipramine potently inhibits serotonin and norepinephrine reuptake (Kis = 7.4 and 96 nM, respectively). It also is an antagonist at histamine, muscarinic acetylcholine, α1-adrenergic, and dopamine receptors (Kds = 31, 37, 38, and 190 nM for H1, M1, α1, and D2, respectively).

Chemical Properties

Off-White Solid

Originator

Anafranil,Ciba Geigy,Switz.,1968

Uses

Potent, selective 5-HT uptake blocker

Uses

Serotonin reuptake inhibitor. Antidepressant; antiobsessional agent

Uses

anti-depressant, serotonin uptake inhibitor

Definition

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.

Manufacturing Process

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.

brand name

Anafranil (Tyco).

Therapeutic Function

Antidepressant

General Description

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.

Biological Activity

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 aggression and anxiety (separation).
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).

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 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.

Metabolism

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

Raw materials

Dimethyl sulfoxide

Preparation Products

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Clomipramine hydrochloride Suppliers

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View Lastest Price from Clomipramine hydrochloride manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Clomipramine hydrochloride 17321-77-6
Price
US $0.00/KG
Min. Order
1KG
Purity
99%,USP
Supply Ability
500kg/month
Release date
2021-07-23
Hebei Weibang Biotechnology Co., Ltd
Product
Clomipramine hydrochloride 17321-77-6
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
100 mt
Release date
2024-11-07
Hebei Yanxi Chemical Co., Ltd.
Product
Clomipramine hydrochloride 17321-77-6
Price
US $40.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
10 tons
Release date
2023-09-07

17321-77-6, Clomipramine hydrochlorideRelated Search:

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  • 17321-77-6
  • C19H23ClN2ClH
  • C19H23CIN2HCl
  • C19H24Cl2N2
  • C19H23ClN2HCl
  • 35131
  • Tricyclic antidepressant; inhibits serotonin and norepinephrine transporters.
  • ANAFRANIL
  • Other APIs
  • Serotonin receptor
  • Amines
  • Heterocycles
  • Intermediates & Fine Chemicals