106083-71-0

Basic information

• Product Name: (+)-(2S,3S)-2-(3-chlorophenyl)-3,5,5-trimethylmorpholin-2-ol
• Synonyms: (+)-(2S,3S)-2-(3-chlorophenyl)-3,5,5-trimethyl-2-morpholinol hydrochloride;(2S,3S)-2-(3-Chlorophenyl)-3,5,5-trimethyl-2-morpholinol hydrochloride;(2S,3S)-Hydroxybupropion hydrochloride;GW 353162;SS-hydroxybupropion hydrochloride;(+)-(2S,3S)-2-(3-chlorophenyl)-3,5,5-trimethylmorpholin-2-ol;Bupropion Morpholinol IMpurity;Bupropion Morpholinol IMpurity (HCl Salt)
• CAS NO: 106083-71-0
• Molecular Formula: C13H18ClNO2
• Molecular Weight: 255.74052
• Mol File: 106083-71-0.mol

Chemical Properties

• Boiling Point: 386.6°Cat760mmHg
• Flash Point: 187.6°C
• Appearance: white to tan/
• Density: 1.144g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.523
• Storage Temp.: ?20°C
• Solubility: DMSO: ≥12mg/mL
• CAS DataBase Reference: (+)-(2S,3S)-2-(3-chlorophenyl)-3,5,5-trimethylmorpholin-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(2S,3S)-2-(3-chlorophenyl)-3,5,5-trimethylmorpholin-2-ol(106083-71-0)
• EPA Substance Registry System: (+)-(2S,3S)-2-(3-chlorophenyl)-3,5,5-trimethylmorpholin-2-ol(106083-71-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 106083-71-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(+)-(2S,3S)-2-(3-chlorophenyl)-3,5,5-trimethylmorpholin-2-ol is used as an active metabolite for the treatment of depression and anxiety disorders due to its role in the metabolism of bupropion. It contributes to the therapeutic effects of bupropion by modulating neurotransmitter levels in the brain, leading to improved mood and reduced anxiety symptoms.
Used in Antidepressant Applications:
(+)-(2S,3S)-2-(3-chlorophenyl)-3,5,5-trimethylmorpholin-2-ol is used as an antidepressant agent, playing a significant role in the treatment of major depressive disorder. It helps alleviate depressive symptoms by influencing the levels of neurotransmitters such as dopamine and norepinephrine, which are crucial for mood regulation.
Used in Antianxiety Applications:
(+)-(2S,3S)-2-(3-chlorophenyl)-3,5,5-trimethylmorpholin-2-ol is used as an antianxiety agent, assisting in the management of anxiety disorders. Its anxiolytic properties are attributed to its ability to modulate neurotransmitter levels, particularly dopamine, which is known to play a role in anxiety regulation.

Biochem/physiol Actions

(2S,3S)-hydroxybupropion is a dopamine transporter (DAT) and norepinephrine transporter (NET) transporters inhibitor and nicotinic acetylcholine receptor (nAChR) family modulator. Hydroxybupropions were reported to contribute to antidepressant and perhaps smoking cessation activities. Both (2S,3S) and (2R,3R) metabolites reverse affective and somatic withdrawal signs in nicotine-dependent mice, but (2S,3S)-hydroxybupropion is more potent. (2S,3S)-hydroxybupropion significantly decreases the development of nicotine reward in mice.

InChI:InChI=1/C13H18ClNO2/c1-9-13(16,17-8-12(2,3)15-9)10-5-4-6-11(14)7-10/h4-7,9,15-16H,8H2,1-3H3/t9-,13+/m0/s1

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Relevant articles and documents

ENZYME-CATALYZED DYNAMIC KINETIC RESOLUTION PROCESS FOR PREPARING (+)-(2S, 3S)-2-(3-CHLOROPHENYL)-3,5,5-TRIMETHYL-2-MORPHOLINOL, SALTS, AND SOLVATES THEREOF

A process for preparing (+)-(2S, 3S)-2-(3-chlorophenyl)-3,5,5-trimethyl-2-morpholinol, pharmaceutically acceptable salts and solvates thereof such as the (+)-(2S, 3S)-2-(3-chlorophenyl)-3,5,5-trimethyl-2-morpholinol hydrochloride salt via enzyme-cataly

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Methods are disclosed which utilize metabolites of bupropion for treating sexual dysfunction.