CAS 71320-77-9|Moclobemide

Introduction：Basic information about CAS 71320-77-9|Moclobemide, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Moclobemide BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Articles47
7. Synonyms

Common Name	Moclobemide
CAS Number	71320-77-9	Molecular Weight	268.739
Density	1.2±0.1 g/cm3	Boiling Point	447.7±40.0 °C at 760 mmHg
Molecular Formula	C₁₃H₁₇ClN₂O₂	Melting Point	137°C
MSDS	ChineseUSA	Flash Point	224.6±27.3 °C
Symbol	GHS05, GHS07	Signal Word	Danger

Names

Name	moclobemide
Synonym	More Synonyms

Moclobemide BiologicalActivity

Description	Moclobemide(Ro111163) is a reversible monoamine oxidase inhibitor (MAOI) selective for isoform A (RIMA) used to treat major depressive disorder.Target: Monoamine OxidaseMoclobemide orally administered 2 hours before decapitation preferentially inhibits MAO-A and PEA in rat brain with ED50 of 7.6 μmol/kg and 78 μmol/kg, respectively. Moclobemide orally administered 2 hours before decapitation preferentially inhibits MAO-A and PEA in rat liver with ED50 of 8.4 μmol/kg and 6.6 μmol/kg, respectively. Moclobemide (0.1 mM), which inhibits brain MAO-A activity by over 80%, does not affect benzylamine oxidase (rat heart) and diamine oxidase (rat small intestine) activity in vitro [1]. Moclobemide (10 mM-100 mM) includes in the culture medium during anoxia or with glutamate significantly increases in a concentration-dependent manner the amount of surviving neurons compared to controls in neuronal-astroglial cultures from rat cerebral cortex [2].Moclobemide (10 mg/kg p.o.) induces a significant decrease of all monoamine metabolites measured in rat brain [1]. Moclobemide, given via the drinking water (4.5 mg/kg/day), produces significant decreases in adrenal weight of rats after 5 (-23%) and 7 weeks (-16%) of treatment. Moclobemide upregulates hippocampal mineralocorticoid receptor (MR) levels in rats by 65%, 76% and 19% at 2 weeks, 5 weeks and 7 weeks of treatment, and upregulates Glucocorticoid receptor (GR) levels in this limbic brain structure by 10% at 5 weeks. Moclobemide treatment (5 weeks, 4.5 mg/kg/day) significantly attenuates stress (30 min novel environment)-induced plasma ACTH (-35%) and corticosterone (-29%) levels [3].
Related Catalog	Signaling Pathways >>Neuronal Signaling >>Monoamine OxidaseResearch Areas >>Neurological Disease
References	[1]. Da Prada, M., et al., Neurochemical profile of moclobemide, a short-acting and reversible inhibitor of monoamine oxidase type A. J Pharmacol Exp Ther, 1989. 248(1): p. 400-14. [2]. Verleye, M., et al., Moclobemide attenuates anoxia and glutamate-induced neuronal damage in vitro independently of interaction with glutamate receptor subtypes. Brain Res, 2007. 1138: p. 30-8. [3]. Reul, J.M., et al., Hypothalamic-pituitary-adrenocortical axis changes in the rat after long-term treatment with the reversible monoamine oxidase-A inhibitor moclobemide. Neuroendocrinology, 1994. 60(5): p. 509-19.

Description

Moclobemide(Ro111163) is a reversible monoamine oxidase inhibitor (MAOI) selective for isoform A (RIMA) used to treat major depressive disorder.Target: Monoamine OxidaseMoclobemide orally administered 2 hours before decapitation preferentially inhibits MAO-A and PEA in rat brain with ED50 of 7.6 μmol/kg and 78 μmol/kg, respectively. Moclobemide orally administered 2 hours before decapitation preferentially inhibits MAO-A and PEA in rat liver with ED50 of 8.4 μmol/kg and 6.6 μmol/kg, respectively. Moclobemide (0.1 mM), which inhibits brain MAO-A activity by over 80%, does not affect benzylamine oxidase (rat heart) and diamine oxidase (rat small intestine) activity in vitro [1]. Moclobemide (10 mM-100 mM) includes in the culture medium during anoxia or with glutamate significantly increases in a concentration-dependent manner the amount of surviving neurons compared to controls in neuronal-astroglial cultures from rat cerebral cortex [2].Moclobemide (10 mg/kg p.o.) induces a significant decrease of all monoamine metabolites measured in rat brain [1]. Moclobemide, given via the drinking water (4.5 mg/kg/day), produces significant decreases in adrenal weight of rats after 5 (-23%) and 7 weeks (-16%) of treatment. Moclobemide upregulates hippocampal mineralocorticoid receptor (MR) levels in rats by 65%, 76% and 19% at 2 weeks, 5 weeks and 7 weeks of treatment, and upregulates Glucocorticoid receptor (GR) levels in this limbic brain structure by 10% at 5 weeks. Moclobemide treatment (5 weeks, 4.5 mg/kg/day) significantly attenuates stress (30 min novel environment)-induced plasma ACTH (-35%) and corticosterone (-29%) levels [3].

Related Catalog

Signaling Pathways >>Neuronal Signaling >>Monoamine OxidaseResearch Areas >>Neurological Disease

References

[1]. Da Prada, M., et al., Neurochemical profile of moclobemide, a short-acting and reversible inhibitor of monoamine oxidase type A. J Pharmacol Exp Ther, 1989. 248(1): p. 400-14.

[2]. Verleye, M., et al., Moclobemide attenuates anoxia and glutamate-induced neuronal damage in vitro independently of interaction with glutamate receptor subtypes. Brain Res, 2007. 1138: p. 30-8.

[3]. Reul, J.M., et al., Hypothalamic-pituitary-adrenocortical axis changes in the rat after long-term treatment with the reversible monoamine oxidase-A inhibitor moclobemide. Neuroendocrinology, 1994. 60(5): p. 509-19.

Chemical & Physical Properties

Density	1.2±0.1 g/cm3
Boiling Point	447.7±40.0 °C at 760 mmHg
Melting Point	137°C
Molecular Formula	C₁₃H₁₇ClN₂O₂
Molecular Weight	268.739
Flash Point	224.6±27.3 °C
Exact Mass	268.097870
PSA	41.57000
LogP	0.84
Vapour Pressure	0.0±1.1 mmHg at 25°C
Index of Refraction	1.550
InChIKey	YHXISWVBGDMDLQ-UHFFFAOYSA-N
SMILES	O=C(NCCN1CCOCC1)c1ccc(Cl)cc1
Storage condition	Room temp

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CV2462000

CHEMICAL NAME :: Benzamide, 4-chloro-N-(2-(4-morpholinyl)ethyl)-

CAS REGISTRY NUMBER :: 71320-77-9

LAST UPDATED :: 199803

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C13-H17-Cl-N2-O2

MOLECULAR WEIGHT :: 268.77

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 5 mg/kg/5W-I

TOXIC EFFECTS :: Skin and Appendages - hair

REFERENCE :: HUPSEC Human Psychopharmacology. (John Wiley & Sons Ltd., Baffins Lane, Chichester, W.Sussex PO19 1UD, United Kingdom) V.1- 1986- Volume(issue)/page/year: 12,81,1997

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 19 mg/kg

TOXIC EFFECTS :: Behavioral - sleep Behavioral - hallucinations, distorted perceptions Gastrointestinal - nausea or vomiting

REFERENCE :: JCLPDE Journal of Clinical Psychiatry. (Physicians Postgraduate Press, Inc., POB 240008, Memphis, TN 38124) V.39- 1978- Volume(issue)/page/year: 47,438,1986

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 66 mg/kg/11D-I

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

REFERENCE :: LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 346,1032,1995

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 12600 mg/kg/14D-I

TOXIC EFFECTS :: Blood - thrombocytopenia Blood - leukemia Skin and Appendages - dermatitis, other (after systemic exposure)

REFERENCE :: LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 347,1329,1996

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 707 mg/kg

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

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #4210754

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 591 mg/kg

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

REFERENCE :: EJMCA5 European Journal of Medicinal Chemistry--Chimie Therapeutique. (Editions Scientifiques Elsevier, 29 rue Buffon, F-75005, Paris, France) V.9- 1974- Volume(issue)/page/year: 31,909,1996

Safety Information

Symbol	GHS05, GHS07
Signal Word	Danger
Hazard Statements	H302-H315-H318-H335
Precautionary Statements	P261-P280-P305 + P351 + P338
Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes	Xn: Harmful;
Risk Phrases	R22
Safety Phrases	S26-S39
RIDADR	3249
RTECS	CV2462000
Packaging Group	III
Hazard Class	6.1(b)

Articles47

Antidepressant-like effect of the novel MAO inhibitor 2-(3,4-dimethoxy-phenyl)-4,5-dihydro-1H-imidazole (2-DMPI) in mice.

Prog. Neuropsychopharmacol. Biol. Psychiatry 39(1) , 31-9, (2012)

Monoamine oxidase (MAO) inhibitors were the first antidepressant drugs to be prescribed and are still used today with great success, especially in patients resistant to other antidepressants. In this ...

[Serotonin syndrome in the course of drug-poisoning--case presentation].

Prz. Lek. 68(8) , 523-6, (2011)

Serotonin syndrome is caused by excess serotonin in the central nervous system. It usually occurs as adverse drug-therapy (neuroleptic agents, monoamine oxidase inhibitors, serotonin reuptake inhibito...

[Obstructive sleep apnoea syndrome as the cause of atypical depression].

Fortschr. Neurol. Psychiatr. 79(9) , 531-4, (2011)

Sleep apnoea is a common disorder presenting with somatic comorbidities and psychiatric symptoms. This case report describes a 43-year-old man with an organic depressive disorder due to obstructive sl...

Synonyms

4-chloro-N-[2-(morpholin-4-yl)ethyl]benzamide

Moclamide

moclbemide

Manefix

Moclobemide

aurorix

4-Chloro-N-(2-(4-morpholinyl)ethyl)benzamide

4-Chloro-N-[2-(4-morpholinyl)ethyl]benzamide

MFCD00865388

Moclobemidum

MODOBEMDE

ro11-1163

Moclaime

Benzamide, 4-Chloro-N-(2-(4-morpholinyl)ethyl)-

p-Chloro-N-(2-morpholinoethyl)benzamide

UNII-PJ0Y7AZB63

manerix

Benzamide, 4-chloro-N-[2-(4-morpholinyl)ethyl]-

Moclamine

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