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

• ChemBase ID: 1042
• Molecular Formular: C13H17ClN2O2
• Molecular Mass: 268.73928
• Monoisotopic Mass: 268.09785547
• SMILES: Clc1ccc(C(=O)NCCN2CCOCC2)cc1
• Canonical SMILES: O=C(c1ccc(cc1)Cl)NCCN1CCOCC1
• InChI: InChI=1S/C13H17ClN2O2/c14-12-3-1-11(2-4-12)13(17)15-5-6-16-7-9-18-10-8-16/h1-4H,5-10H2,(H,15,17)
• InChIKey: YHXISWVBGDMDLQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-chloro-N-[2-(morpholin-4-yl)ethyl]benzamide
• IUPAC Traditional name: moclobemide; arima
• Brand Name: Aurorix; Manerix
• Synonyms: Moclobemida [INN-Spanish]; Moclobemide [Usan:Ban:Inn]; Moclobemidum [INN-Latin]; 4-Chlor-N-(2-morpholinoethyl)benzamid; 4-Chloro-N-(2-(4-morpholinyl)ethyl)benzamide; 4-Chloro-N-(2-morpholin-4-yl-ethyl)-benzamide; Moclamine; Moclamide; Moclobemid; Moclaime; p-Chloro-N-(2-morpholinoethyl)benzamide; moclobemide; Moclobemide; 4-chloro-N-[2-(4-morpholinyl)ethyl]benzamide; Aurorix; Moclobemide; Ro-11-1163, Aurorix, Manerix, Moclamine, p-Chloro-N-(2-morpholinoethyl)benzamide

Database IDs

• CAS Number: 71320-77-9
• MDL Number: MFCD00865388
• PubChem SID: 160964505; 46504667
• PubChem CID: 4235
• ATC CODE: N06AG02
• CHEMBL: 86304
• Chemspider ID: 4087
• DrugBank ID: DB01171
• KEGG ID: D02561
• Unique Ingredient Identifier: PJ0Y7AZB63
• Wikipedia Title: Moclobemide

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.732517
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.8195106
• LogD (pH = 7.4): 1.4341191
• Log P: 1.4517509
• Molar Refractivity: 71.9315 cm^3
• Polarizability: 27.590597 Å^3
• Polar Surface Area: 41.57 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.56
• LOG S: -2.38
• Solubility (Water): 1.12e+00 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL; Isopropanol; Methanol
• Apperance: white solid; White to Off-White Solid
• Melting Point: 135-137°C
• Hydrophobicity(logP): 1.5

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: CV2462000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 22-37/38-41
• Safety Statements: 26-39
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H315-H318-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: room temp

Pharmacology Properties

• Target: MAO
• Admin Routes: oral
• Bioavailability: 60% after first dose, >80% after first week of treatment
• Excretion: renally/in urine
• Half Life: 1 to 2 hours
• Metabolism: Liver
• Legal Status: Rx-only; not a controlled substance
• Pregnancy Category: B3 (Australia)

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C13H17ClN2O2

DETAILS

DrugBank - DB01171

• Drug Groups: approved
• Description: A reversible monoamine oxidase inhibitor (MAOI) selective for isoform A (RIMA) used to treat major depressive disorder.
• Indication: For the treatment of depression.
• Pharmacology: Moclobemide belongs to a class of MAOI antidepressants known as reversible inhibitors of monoamine oxidase type-A (RIMAs). The primary role of monoamine oxidase MAO lies in the metabolism of and regulation of the levels of monoamines (serotonin, norepinephrine, and dopamine). Within neurons, MAO appears to regulate the levels of monoamines released upon synaptic firing. Since depression is associated with low levels of monoamines, the inhibition of MAO serves to ease depressive symptoms. RIMAs demonstrate transient inhibition of the substrate binding site of MAO-A as well as competitive displacement from this site by bioamines. The RIMAs are distinguished from the older monoamine oxidase inhibitors (MAOIs) by their selectivity and reversibility.
• Toxicity: LD50 (mouse) is 730mg/kg and LD50 (rat) is 1,300mg/kg. Signs of toxicity include hypertension, drowsiness, dizziness, confusion, tremors, headache, agitation, muscle rigidity and seizures.
• Affected Organisms: Humans and other mammals
• Biotransformation: Moclobemide is almost completely metabolized in the liver by Cytochrome P450 2C19 and 2D6.
• Absorption: Well absorbed from the gastrointestinal tract (> 95%). The presence of food reduces the rate but not the extent of absorption. Hepatic first pass metabolism reduces bioavailability to 45-70% following administration of a single dose, but increases to 80% with multiple dosing as a result of saturation of the first pass effect. Peak plasma concentrations are reached within 1 - 2 hours following oral administration.
• Half Life: 1-2 hours (4 hours in cirrhotic patients); metabolites are renally excreted
• Protein Binding: Approximately 50% (primarily to albumin)
• External Links: Wikipedia

Sigma Aldrich - M3071

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.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. M3071.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - M481000

A reversible monoamine oxidase inhibitor.

REFERENCES

• Wiesel, F.A., et al.: Eur. J. Clin. Pharmacol., 28, 89 (1985)
• Burkard, W.P., et al.: J. Pharmacol. Exp. Ther., 248, 391 (1989)