CAS 303-49-1|Clomipramine

Introduction：Basic information about CAS 303-49-1|Clomipramine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Clomipramine BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Customs
7. Synonyms

Common Name	Clomipramine
CAS Number	303-49-1	Molecular Weight	314.852
Density	1.1±0.1 g/cm3	Boiling Point	434.2±45.0 °C at 760 mmHg
Molecular Formula	C₁₉H₂₃ClN₂	Melting Point	/
MSDS	/	Flash Point	216.4±28.7 °C

Names

Name	clomipramine
Synonym	More Synonyms

Clomipramine BiologicalActivity

Description	Clomipramine (Chlorimipramine) is a potent 5-HT reuptake blocker with the IC50 value of 1.5 nM. Clomipramine is a tricyclic antidepressant that can be used for the research of depression and obsessive compulsive disorder (OCD)[1].
Related Catalog	Research Areas >>Neurological DiseaseSignaling Pathways >>Neuronal Signaling >>Serotonin Transporter
In Vitro	Clomipramine can inhibit reuptake of both noradrenaline and 5-HT, although Clomipramine inhibits 5-HT reuptake more strongly than it inhibits noradrenaline reuptake[1]. The antidepressant Clomipramine inhibits both venom AChE as well as human serum BChE in a concentration-dependent manner but has no effect on AChE in the rat brain striatum[2]. Clomipramine interferes with the autophagic flux and severely compromises the viability of tumorigenic cells upon cytotoxic stress[3]. Clomipramine reduces autophagy in neuronal primary cultures. Clomipramine (1 and 5 µM) negatively regulates neuronal autophagic pathway in primary cultured cells[3]. Western Blot Analysis[3] Cell Line: Primary cortical neurons Concentration: 1 and 5 µM Incubation Time: 12, 24 and 48 hours Result: Enhanced the LC3-I conversion to LC3-II in a concentration-dependent manner at all analyzed time points.
In Vivo	Clomipramine (5-20 mg/kg; i.p) elicits significant hyperglycemia in mice. Clomipramine induces hyperglycemia in mice by blocking the 5-HT2B and/or 5-HT2C receptors, which results in facilitation of adrenaline release. In mice, Clomipramine reduces immobility in the forced swimming test, which is the behavioral model for antidepressants. Clomipramine also inhibits the OCD animal model, marble burying behavior in mice[1]. Clomipramine (20 mg/kg) decreases autophagic flux in murine tissues[3]. Animal Model: C57BL/6 J mice (6 weeks of age and 22 to 25 g)[3] Dosage: 20 mg/kg Administration: Treated intraperitoneally for 21 days Result: Both LC3-II and p62 were significantly increased in the liver of Clomipramine treated mice compared to vehicle treated ones.
References	[1]. Yumi Sugimoto, et al. The tricyclic antidepressant Clomipramine increases plasma glucose levels of mice. J Pharmacol Sci. 2003 Sep;93(1):74-9. [2]. Mushtaq Ahmed, et al. Comparative study of the inhibitory effect of antidepressants on cholinesterase activity in Bungarus sindanus (krait) venom, human serum and rat striatum. J Enzyme Inhib Med Chem. 2008 Dec;23(6):912-7. [3]. Federica Cavaliere,The tricyclic antidepressant Clomipramine inhibits neuronal autophagic flux. Sci Rep. 2019 Mar 19;9(1):4881.

Chemical & Physical Properties

Density	1.1±0.1 g/cm3
Boiling Point	434.2±45.0 °C at 760 mmHg
Molecular Formula	C₁₉H₂₃ClN₂
Molecular Weight	314.852
Flash Point	216.4±28.7 °C
Exact Mass	314.154968
PSA	6.48000
LogP	5.39
Vapour Pressure	0.0±1.0 mmHg at 25°C
Index of Refraction	1.582
InChIKey	GDLIGKIOYRNHDA-UHFFFAOYSA-N
SMILES	CN(C)CCCN1c2ccccc2CCc2ccc(Cl)cc21
Water Solubility	H2O: 25 mg/mL

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: HN9050000

CHEMICAL NAME :: 5H-Dibenz(b,f)azepine, 10,11-dihydro-3-chloro-5-(3-(dimethylamino)propyl)-

CAS REGISTRY NUMBER :: 303-49-1

BEILSTEIN REFERENCE NO. :: 1323477

LAST UPDATED :: 199612

DATA ITEMS CITED :: 16

MOLECULAR FORMULA :: C19-H23-Cl-N2

MOLECULAR WEIGHT :: 314.89

WISWESSER LINE NOTATION :: T C676 BN&T&J B3N1&1 EG

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 357 ug/kg

TOXIC EFFECTS :: Gastrointestinal - nausea or vomiting

REFERENCE :: JCPYDR Journal of Clinical Pyschopharmacology. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1981- Volume(issue)/page/year: 2,215,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 10 mg/kg/5D-I

TOXIC EFFECTS :: Vascular - BP elevation not characterized in autonomic section

REFERENCE :: BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 1,406,1971

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 30 mg/kg

TOXIC EFFECTS :: Behavioral - coma Gastrointestinal - changes in structure or function of endocrine pancreas Gastrointestinal - decreased motility or constipation

REFERENCE :: JTCTDW Journal of Toxicology, Clinical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.19- 1982- Volume(issue)/page/year: 32,425,1994

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 3400 ug/kg/47M-I

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Cardiac - cardiomyopathy including infarction

REFERENCE :: BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 3,698,1972

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 613 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: TXCYAC Toxicology. (Elsevier Scientific Pub. Ireland, Ltd., POB 85, Limerick, Ireland) V.1- 1973- Volume(issue)/page/year: 24,335,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 149 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: TXCYAC Toxicology. (Elsevier Scientific Pub. Ireland, Ltd., POB 85, Limerick, Ireland) V.1- 1973- Volume(issue)/page/year: 24,335,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 380 mg/kg

TOXIC EFFECTS :: Behavioral - wakefulness Behavioral - changes in motor activity (specific assay)

REFERENCE :: GWXXBX German Offenlegungsschrift Patent Document. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #2618152

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 150 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 21,448,1978

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 27 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: APSXAS Acta Pharmaceutica Suecica. (Apotekarsocieteten-Farmacevtiska Foereningen, Box 1136, S-111, 81 Stockholm, Sweden) V.1- 1964- Volume(issue)/page/year: 13,485,1976 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2857 ug/kg

SEX/DURATION :: male 4 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - impotence

REFERENCE :: CJPSDF Canadian Journal of Psychiatry. (Keith Health Care Communications, 289 Rutherford Rd. South, Suite 11, Brampton, ON L6W 3R9, Canada) Volume(issue)/page/year: 27,148,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 50 mg/kg

SEX/DURATION :: female 38-47 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 24(1),42A,1981

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 6850 mg/kg

SEX/DURATION :: female 1-39 week(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - other neonatal measures or effects

REFERENCE :: JTCTDW Journal of Toxicology, Clinical Toxicology. (Marcel Dekker, 270 Madison Ave., New York, NY 10016) V.19- 1982- Volume(issue)/page/year: 29,479,1991

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 420 mg/kg

SEX/DURATION :: lactating female 21 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain) Reproductive - Effects on Newborn - behavioral Reproductive - Effects on Newborn - physical

REFERENCE :: PSCHDL Psychopharmacology (Berlin). (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.47- 1976- Volume(issue)/page/year: 56,93,1978

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 400 mg/kg

SEX/DURATION :: female 20 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Effects on Newborn - live birth index (measured after birth) Reproductive - Effects on Newborn - physical

REFERENCE :: PSCHDL Psychopharmacology (Berlin). (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.47- 1976- Volume(issue)/page/year: 56,93,1978

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 66 mg/kg

SEX/DURATION :: female 1-22 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - behavioral

REFERENCE :: PSCHDL Psychopharmacology (Berlin). (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.47- 1976- Volume(issue)/page/year: 79,236,1983

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 150 mg/kg

SEX/DURATION :: female 7-21 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - Central Nervous System

REFERENCE :: JNGSE8 Journal of Neural Transmission. General Section. (Springer-Verlag, Postfach 367, A-1011, Vienna, Austria) V.78- 1989- Volume(issue)/page/year: 90,113,1992

Safety Information

Hazard Codes	Xn: Harmful;
Risk Phrases	R20/21/22
Safety Phrases	S36
WGK Germany	3
RTECS	HN9055000
HS Code	2933990090

Customs

HS Code	2933990090
Summary	2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Synonyms

3-Chloroimipramine

Chlorimipramine

3-Chloro-10,11-dihydro-N,N-dimethyl-5H-dibenz[b,f]azepine-5-propanamine

5H-Dibenz(b,f)azepine-5-propanamine, 3-chloro-10,11-dihydro-N,N-dimethyl-

5H-Dibenz[b,f]azepine-5-propanamine, 3-chloro-10,11-dihydro-N,N-dimethyl-

MFCD00069234

Clomipramine

3-(3-chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethylpropan-1-amine

5-(g-Dimethylaminopropyl)-3-chloroiminodibenzyl

3-Chloro-10,11-dihydro-5-(3-dimethylaminopropyl)-5H-dibenz[b,f]azepine

3-chloro-10,11-dihydro-N,N-dimethyl-5H-Dibenz(b,f)azepine-5-propanamine

Hydiphen

Clomipramina

10,11-dihydro-3-chloro-5-(3-(dimethylamino)propyl)-5H-dibenz(b,f)azepine

3-Chloro-5-[3-(dimethylamino)propyl]-10,11-dihydro-5H-dibenz[b,f]azepine

3-(3-Chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-N,N-dimethyl-1-propanamine

Monochlorimipramine

ANAFRANIL

3-(2-chloro-5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethylpropan-1-amine

chloripramine

EINECS 206-144-2

Chlomipramine

Anafranil base

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