244223-89-0

Basic information

• Product Name: (cis-1S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine (R)-mandelate
• CAS NO: 244223-89-0
• Molecular Weight: 458.384
• Mol File: 244223-89-0.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: (cis-1S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine (R)-mandelate(CAS DataBase Reference)
• NIST Chemistry Reference: (cis-1S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine (R)-mandelate(244223-89-0)
• EPA Substance Registry System: (cis-1S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine (R)-mandelate(244223-89-0)

Safety Data

• Hazardous Substances Data: 244223-89-0(Hazardous Substances Data)

Usage

Description

(cis-1S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine (R)-mandelate, commonly known as Savella, is a chemical compound that serves as an antidepressant and antipsychotic medication. It functions as a selective serotonin and norepinephrine reuptake inhibitor (SNRI), enhancing the levels of these neurotransmitters in the brain, which can improve mood, reduce anxiety, and alleviate symptoms of depression and other mood disorders.

Uses

Used in Pharmaceutical Industry:
(cis-1S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine (R)-mandelate is used as an antidepressant and antipsychotic medication for the treatment of fibromyalgia. It is prescribed under the brand name Savella and is available in tablet form for oral administration. (cis-1S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine (R)-mandelate's mechanism of action involves increasing the levels of serotonin and norepinephrine in the brain, which can help improve mood, reduce anxiety, and alleviate symptoms of depression and other mood disorders.

Upstream product

• 611-71-2 (R)-Mandelic Acid 
• 140631-53-4 sertraline 
• 261776-41-4 (4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-ylidene)methylamine 
• 79560-20-6 N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene]methanamine 
• 90-15-3 α-naphthol 
• 95-50-1 1,2-dichloro-benzene 
• 79560-19-3 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one 
• 79617-89-3 cis-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthaleneamine hydrochloride 
• 79617-96-2 Sertraline 
• 611-71-2 MANDELIC ACID 
• 79617-95-1 cis-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-naphthaleneamine 

Downstream Products

• 611-71-2 (R)-Mandelic Acid 
• 54385-47-6 (R)-Mandelsaeure, Natrium-Salz 
• 79559-97-0 sertraline hydrochloride 
• 79617-96-2 Sertraline 

Relevant articles and documents

A low-waste process to sertraline by diastereomeric crystal resolution and waste isomer racemisation

A semi-continuous method for recovering waste sertraline isomers from a diastereomeric crystallisation process is described in which the mother liquors from a highly selective mandelic acid resolution for the (1S,4S) isomer are treated sequentially with S

Resolution of sertraline with (R)-mandelic acid: Chiral discrimination mechanism study

The chiral discrimination mechanism in the resolution of sertraline with mandelic acid was investigated by examining the weak intermolecular interactions (such as hydrogen bond, CH/π, and van der Waals interactions) and molecular packing difference in crystal structures of the resulting diastereomeric salts. A new one-dimensional chain-like hydrogen-bonding network and unique supramolecular packing mode are disclosed. The investigation demonstrated that stable hydrogen-bonding pattern, herringbone-like arrangement of aromatic rings, and planar boundary surface in the hydrophobic region are the three most important structural characteristics expected in less soluble diastereomeric salts. The existence and magnitude of hydrogen bond, CH/π interaction, and van der Waals interaction related to three characteristic structures, determine the stability of diastereomeric salt. The hydrogen bond is not necessarily the dominant factor while the synergy and optimization of all weak intermolecular interactions attribute to the chiral recognition.

Resolution of Racemic Organic Acids with (1S, 4S)-4[3,4-Dichlorophenyl]-1,2,3,4-Tetrahydro-N-Methyl-1-Naphthaloneamine

The present invention relates to novel chiral resolving agents and a process for resolution of racemic organic acids and their derivatives of the formula (+, ?)—R1R2CHCOOR3 with Cis-(1S,4S)-4[3,4-dichlorophenyl]-1,2,3,4-tetrahydro-N-methyl-1-naphthaloneamine and its Cis-(1R,4R)-isomer as well as Trans-(1S,4R)-4[3,4-dichlorophenyl]-1,2,3,4-tetrahydro-N-methyl-1-naphthaloneamine and its Trans-(1R,4S)-isomer.