84145-89-1

Basic information

• Product Name: Almoxatone
• Synonyms: Almoxatone;[5R,(+)]-3-[4-[(3-Chlorobenzyl)oxy]phenyl]-5-[(methylamino)methyl]-2-oxazolidinone;[5R,(+)]-3-[4-[(3-Chlorophenyl)methoxy]phenyl]-5-[(methylamino)methyl]-2-oxazolidinone;MD-240928;( -)-(R)-3-(4-(2-Chlorbenzyloxy)phenyl)-5-((methylamino)methyl)-2-oxazolidinon;( )-(R)-3-(p-((m-Chlorobenzyl)oxy)phenyl)-5-((methylamino)methyl)-2-oxazolidinone;Almoxaton;Almoxatone [inn]
• CAS NO: 84145-89-1
• Molecular Formula: C₁₈H₁₉ClN₂O₃
• Molecular Weight: 346.812
• Mol File: 84145-89-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 490.5°C at 760 mmHg
• Flash Point: 250.5°C
• Appearance: /
• Density: 1.263g/cm³
• Vapor Pressure: 9.07E-10mmHg at 25°C
• Refractive Index: 1.589
• CAS DataBase Reference: Almoxatone(CAS DataBase Reference)
• NIST Chemistry Reference: Almoxatone(84145-89-1)
• EPA Substance Registry System: Almoxatone(84145-89-1)

Safety Data

• Hazardous Substances Data: 84145-89-1(Hazardous Substances Data)

Usage

Chemical Classification

Almoxatone is a synthetic chemical compound.

Pharmacological Class

It belongs to the class of monoamine oxidase inhibitors (MAOIs).

Mechanism of Action

Almoxatone inhibits the activity of monoamine oxidase, an enzyme involved in the metabolism of neurotransmitters like serotonin and dopamine in the brain.

Effect

By blocking the breakdown of neurotransmitters, it increases their levels in the brain, leading to improved mood and reduced symptoms of depression.

Therapeutic Potential

Investigated for potential therapeutic effects in Parkinson's disease and other neurological disorders.

Interactions

Carries a risk of interactions with certain foods and medications.

Side Effects

Can cause potentially serious side effects if not used with caution under the supervision of a healthcare professional.

InChI:InChI=1/C18H19ClN2O3/c1-20-10-17-11-21(18(22)24-17)15-5-7-16(8-6-15)23-12-13-3-2-4-14(19)9-13/h2-9,17,20H,10-12H2,1H3/t17-/m1/s1

Upstream product

• 824-78-2 4-nitrophenol sodium salt 
• 620-20-2 1-Chloro-3-chloromethyl-benzene 
• 87823-53-8 (R)-3-<4-<(3-chlorophenyl)methoxy>phenyl>-5-(hydroxymethyl)-2-oxazolidinone 
• 130641-78-0 (R)-3-<<4-<(3-chlorophenyl)methoxy>phenyl>amino>-1,2-propanediol 
• 57181-88-1 4-<(3-chlorophenyl)methoxy>aniline 
• 130641-75-7 4-<(3-chlorophenyl)methoxy>nitrobenzene 
• 130641-84-8 Methanesulfonic acid (R)-3-[4-(3-chloro-benzyloxy)-phenyl]-2-oxo-oxazolidin-5-ylmethyl ester 
• 74-89-5 methylamine 

Relevant articles and documents

5-(Aminomethyl)-3-aryl-2-oxazolidinones. A novel class of mechanism-sased inactivators of monoamine oxidase B

The mechanism of inactivation of monoamine oxidase (MAO) by 5-(aminomethyl)-3-aryl-2-oxazolidinones has been investigated. (R)- and (S)-3-[4-[(3-chlorophenyl)methoxy]phenyl]-5-[(methylamino)methyl]-2- oxazolidinone (1) exhibit all of the properties of a mechanism-based inactivator. Several other analogues of 1 also inactivate MAO. Inactivation of MAO by (R)- and (S)-[methoxy-3H]-1 and by [methoxy- 3H]-3-(4-methoxyphenyl)-5-[(methylamino)methyl]-2-oxazolidinone (15, R = 3H) led to incorporation of 1.0, 1.2, and 2.1 equiv of tritium per enzyme molecule after denaturation, indicating that a covalent bond between the oxazolidinones and MAO is formed. The partition ratios, determined from the amount of radioactive non-amines generated per tritium incorporated into the enzyme, were 17.6 and 10.9 for the R and S isomers, respectively. Inactivation of MAO by (R)- and (S)-[carboxy-14C]-1 resulted in release of 4.5 and 3.0 equiv of 14CO2, respectively. However, in addition to the loss of 14CO2 there also was incorporation of 1.5 and 1.0 equiv of 14C, respectively, into the enzyme after denaturation. The flavin spectrum indicated that the flavin was reduced after inactivation, but upon denaturation the spectrum returned to that of the oxidized form, suggesting that attachment is to an amino acid residue, not to the flavin. 5-(Aminomethyl)-3-(4-cyanophenyl)-2-oxazolidinone inactivates MAO at a rate comparable to or faster than does the corresponding 4-methoxyphenyl analogue, suggesting that there is little or no electronic effect of ring substitution on the rate of inactivation. All of these results support an inactivation mechanism that involves one-electron oxidation of the amine to the amine radical cation, followed by proton removal to give the α radical, which can partition among three pathways (Scheme V): radical combination with an active-site amino acid residue radical to give inactive enzyme, decomposition of the oxazolidinone ring with loss of CO2, and second electron transfer to give the corresponding aldehyde product.