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Moclobemide

Product Name
Moclobemide
CAS No.
71320-77-9
Chemical Name
Moclobemide
Synonyms
Moclobemide (Ro 111163);4-chloro-N-(2-morpholinoethyl)benzamide;Manefix;CS-1682;manerix;aurorix;Moclaime;Moclamine;MODOBEMDE;Moclamide
CBNumber
CB0281564
Molecular Formula
C13H17ClN2O2
Formula Weight
268.74
MOL File
71320-77-9.mol
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Moclobemide Property

Melting point:
137°C
Boiling point:
447.7±40.0 °C(Predicted)
Density 
1.206±0.06 g/cm3(Predicted)
storage temp. 
room temp
solubility 
DMSO: >20mg/mL
pka
14.26±0.46(Predicted)
form 
solid
color 
white
Merck 
14,6226
CAS DataBase Reference
71320-77-9(CAS DataBase Reference)
NIST Chemistry Reference
Moclobemide(71320-77-9)
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Safety

Hazard Codes 
Xn,T+
Risk Statements 
22-37/38-41-26/27/28
Safety Statements 
26-39-45-36/37/39-22
RIDADR 
3249
WGK Germany 
2
RTECS 
CV2462000
HazardClass 
6.1(b)
PackingGroup 
III
HS Code 
29349990
Hazardous Substances Data
71320-77-9(Hazardous Substances Data)
Toxicity
LD50 in rats (mg/kg): 707 orally (Burkard, Wyss)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H318Causes serious eye damage

H335May cause respiratory irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
M3071
Product name
Moclobemide
Purity
≥98% (HPLC), solid
Packaging
10mg
Price
$178
Updated
2024/03/01
Sigma-Aldrich
Product number
M3071
Product name
Moclobemide
Purity
≥98% (HPLC), solid
Packaging
50mg
Price
$707
Updated
2024/03/01
TCI Chemical
Product number
M2733
Product name
Moclobemide
Purity
>98.0%(HPLC)
Packaging
10mg
Price
$129
Updated
2024/03/01
Cayman Chemical
Product number
24361
Product name
Moclobemide
Purity
≥98%
Packaging
1mg
Price
$44
Updated
2024/03/01
Cayman Chemical
Product number
24361
Product name
Moclobemide
Purity
≥98%
Packaging
5mg
Price
$109
Updated
2024/03/01
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Moclobemide Chemical Properties,Usage,Production

Description

Moclobemide is the first of a new generation of non-hydrazine, reversible MAO-A inhibitors useful in the treatment of depression. Moclobemide is a selective inhibitor of MAO-A, allowing tyramine to be metabolized by MAO-B. In controlled studies, moclobemide was clinically superior to desipramine and showed no cholinergic or cardiovascular side-effects. A metabolite is currently under investigation for treatment of Parkinson’s disease,.

Description

Moclobemide (Item No. 24361) is an analytical reference standard categorized as an antidepressant. This product is intended for research and forensic applications.

Chemical Properties

White to Off-White Solid

Originator

Hoffmann-LaRoche (Switzerland)

Uses

A reversible monoamine oxidase inhibitor.

Uses

Antidepressant;Mono amine oxidase inhibitor (Type A)

Definition

ChEBI: A member of the class of benzamides that is benzamide substituted by a chloro group at position 4 and a 2-(morpholin-4-yl)ethyl group at the nitrogen atom. It acts as a reversible monoamine oxidase inhibitor and is used in the treatment of depression.

brand name

Aurorix

Biochem/physiol Actions

Moclobemide is a reversible monoamine oxidase A inhibitor (MAOI); antidepressant. Elimination half-life in humans = 1 -3 hrs; absolute oral bioavailability. Unlike other MAO inhibitors, does not significantly increase blood pressure in humans upon combination with tyramine.

Mechanism of action

Moclobemide is an RIMA that preferentially inhibits MAO-A (~80%) and, to a lesser extent, MAO-B (20–30% inhibition), thereby increasing the concentration of 5-HT, NE, and other catecholamines in the synaptic cleft and in storage sites. During chronic therapy with the MAOIs, adaptive changes at the noradrenergic and serotonergic receptors occur (“downregulation”) as a result of neurotransmitter hypersensitivity because of prolonged concentrations of NE and 5-HT at the postsynaptic receptor. This mechanism is likely the basis for its antidepressant activity. Inhibition of MAO-A by moclobemide is short-acting (maximum, 24 hours) and reversible. This is in contrast to phenelzine, which is nonselective, long-acting, and irreversible in its binding to MAO-A and MAO-B.
The pharmacokinetics for moclobemide are linear only up to 200 mg; at higher doses, nonlinear pharmacokinetics are observed. Although well absorbed from the GI tract, the presence of food reduces the rate but not the extent of absorption of moclobemide. Small quantities of moclobemide are distributed into human breast milk. Moclobemide undergoes a complex metabolism, initially involving morpholine carbon and nitrogen oxidation, deamination, and aromatic hydroxylation. The N-oxide and ring-opened metabolites retain some in vitro MAO-A inhibition. Moclobemide is a weak inhibitor of CYP2D6 in vitro. It is extensively metabolized in the liver by oxidation and is eliminated primarily into the urine as conjugates. Less than 1% of an administered dose of moclobemide is eliminated unmetabolized.
Because moclobemide is partially metabolized by the polymorphic isozymes CYP2C19 and CYP2D6, plasma concentrations of moclobenmide may be affected in patients who are poor metabolizers. In patients who are slow metabolizers, the AUC for moclobemide was 1.5 times greater than the AUC in patients who are extensive metabolizers and receiving the same dose. This increase is within the normal range of variation (up to twofold) typically seen in patients.

Clinical Use

Reversible MAOI:
Depression
Social phobia

Drug interactions

Drug interactions for the RIMAs include interaction with SSRI antidepressants, which can cause the 5-HT syndrome. The effect of stimulant drugs, such as methylphenidate and dextroamphetamine (used to treat ADHD), may be increased. Some over-the-counter cold and hay fever decongestants (i.e., sympathomimetic amines) can have increased stimulant effects. Selegiline, a selective MAO-B used for Parkinson's disease, should not be used concurrently with the RIMAs. Unlike the irreversible MAOIs, no significant interactions with foods occur, because the selective inhibition of MAO-A does not stop the metabolism of tyramine. The RIMAs must not be taken concurrently with a nonreversible MAOI.

Metabolism

Moclobemide is extensively metabolised in the liver, partly by the cytochrome P450 isoenzymes CYP2C19 and CYP2D6. Metabolites of moclobemide and a small amount of unchanged drug are excreted in the urine

storage

Room temperature

References

[1] pisani l, barletta m, soto-otero r, nicolotti o, mendez-alvarez e, catto m, introcaso a, stefanachi a, cellamare s, altomare c, carotti a. discovery, biological evaluation, and structure-activity and -selectivity relationships of 6'-substituted (e)-2-(benzofuran-3(2h)-ylidene)-n-methylacetamides, a novel class of potent and selective monoamine oxidase inhibitors. j med chem. 2013 mar 28;56(6):2651-64.
[2] nair np, ahmed sk, kin nm. biochemistry and pharmacology of reversible inhibitors of mao-a agents: focus on moclobemide. j psychiatry neurosci. 1993 nov;18(5):214-25.

Moclobemide Preparation Products And Raw materials

Raw materials

CHLORIC ACID Acrylamide Triethylamine 4-Chlorobenzoic acid Ethyl chloroformate 2-Bromoethylamine hydrobromide Propionamide 4-Chlorobenzoyl chloride Isopropyl alcohol

Preparation Products

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Moclobemide Suppliers

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View Lastest Price from Moclobemide manufacturers

Jinan Jianfeng Chemical Co., Ltd
Product
Moclobemide 71320-77-9
Price
US $0.00/kg
Min. Order
1kg
Purity
99%min
Supply Ability
5000kg
Release date
2024-08-09
Wuhan Senwayer Century Chemical Co.,Ltd
Product
Moclobemide 71320-77-9
Price
US $0.00-0.00/mg
Min. Order
10mg
Purity
98%
Supply Ability
10kg
Release date
2023-02-10
Nantong Guangyuan Chemicl Co,Ltd
Product
Moclobemide 71320-77-9
Price
US $10.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1000kg
Release date
2023-11-03

71320-77-9, MoclobemideRelated Search:

Olanzapine ISOCARBOXAZID (200 MG) Minoxidil Entacapone Penfluridol Citalopram Trazodone Paroxetine Paroxetine hydrochloride Benzamide Chlorantraniliprole p-Aminobenzamide Difluorochloromethane Moclobemide 4-t-Butylbenzamide AURORA 16306 (2,4-DICHLOROPHENYL)-N-(2-MORPHOLIN-4-YLETHYL)FORMAMIDE

  • moclbemide
  • 4-CHLORO-N[2-(4-MORPHOLINYL)ETHYL]-BENZAMIDE (MOCLOBEMIDE)
  • Ro-11-1163, Aurorix, Manerix, Moclamine, p-Chloro-N-(2-morpholinoethyl)benzamide
  • MODOBEMDE
  • p-Chlor-N-(2-morpholinoethyl)benzamid
  • 4-Chloro-(2-(4-morpholinyl)ethyl)benzamide
  • Moclobemide (base and/or unspecified salts)
  • 4-Chloro-N-[2-(4-morpholinyl)ethyl]benzamide, Aurorix, Moclamine
  • 4-Chloro-N-[2-(4-motpholinyl)ethyl]benzamide
  • Manefix
  • Moclamine
  • 4-chloro-N-(2-morpholinoethyl)benzamide
  • Moclobemide (Ro 111163)
  • 4-Chloro-N-(2-morpholin-4-ylethyl)benzamide
  • CS-1682
  • p-chloro-n-(2-morpholinoethyl)benzamide
  • MOCLOBEMIDE
  • manerix
  • aurorix
  • BENZAMIDE, 4-CHLORO-N-[2-(4-MORPHOLINYL)ETHYL]-
  • 4-chloro-n-(2-(4-morpholinyl)ethyl)-benzamid
  • 4-Chloro-N-(2-(4-morpholinyl)ethyl)benzamide
  • Moclaime
  • Moclamide
  • RO 11-1163
  • ro11-1163
  • Ro-11-1163/000
  • Moclobemide USP/EP/BP
  • MOCLOBAMIDE
  • Moclobemide in methanol
  • 71320-77-9
  • 71320-77-7
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  • Monoamine Oxidase