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Moclobemide

Names

[ CAS No. ]:
71320-77-9

[ Name ]:
Moclobemide

[Synonym ]:
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

Biological Activity

[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 Oxidase
Research 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.


[Related Small Molecules]

Phenelzine (sulfate) | trans-2-Phenylcyclopropylamine hemisulfate salt | Clorgyline hydrochloride | Rosmarinic acid | pargyline hydrochloride | GSK-LSD1 Dihydrochloride | Rasagiline mesylate | Mofegiline hydrochloride | Paeonol | Iproniazid (phosphate) | Safinamide | TVP1022 | Minaprine | Nialamide | Desmethoxyyangonin

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

[ Storage condition ]:
Room temp

MSDS

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)

Synthetic Route

Precursor & DownStream

Articles

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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].

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

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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...


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