101152-94-7

Basic information

• Product Name: (1R,2S)-rel-2-(Aminomethyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide hydrochloride
• Synonyms: F 2207;IXEL;(1R,2S)-REL-2-(AMINOMETHYL)-N,N-DIETHYL-1-PHENYLCYCLOPROPANECARBOXAMIDE HYDROCHLORIDE;(1R,2S)-REL-2-(AMINOMETHYL)-N,N-DIMETHYL-1-PHENYLCYCLOPROPANECARBOXAMIDE HYDROCHLORIDE;TOLEDOMIN;MILNACIPRAN HCL;MILNACIPRAN HYDROCHLORIDE;MIDALCIPRAN
• CAS NO: 101152-94-7
• Molecular Formula: C15H23ClN2O
• Molecular Weight: 282.81
• EINECS: 200-659-6
• Product Categories: Chiral Reagents;Antibiotic Explorer;Intermediates & Fine Chemicals;Pharmaceuticals;Amines;Aromatics;NEGGRAM
• Mol File: 101152-94-7.mol

Chemical Properties

• Melting Point: 179-1810C
• Boiling Point: 393 °C at 760 mmHg
• Flash Point: 9℃
• Appearance: white/solid
• Vapor Pressure: 1.66E-07mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: H2O: 19 mg/mL
• Merck: 14,6194
• CAS DataBase Reference: (1R,2S)-rel-2-(Aminomethyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S)-rel-2-(Aminomethyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide hydrochloride(101152-94-7)
• EPA Substance Registry System: (1R,2S)-rel-2-(Aminomethyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide hydrochloride(101152-94-7)

Safety Data

• Hazard Codes: Xn,T,F
• Statements: 22-39/23/24/25-23/24/25-11
• Safety Statements: 7-16-36/37-45
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: GZ1014010
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 101152-94-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(1R,2S)-rel-2-(Aminomethyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide hydrochloride is used as an antidepressant medication for the treatment of depression. It functions as a selective norepinephrine and serotonin reuptake inhibitor, helping to regulate mood and alleviate depressive symptoms.
Used in Chronic Pain Management:
In 2009, the US Food and Drug Administration (FDA) approved (1R,2S)-rel-2-(Aminomethyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide hydrochloride for the management of fibromyalgia, a chronic pain disorder. It is the third drug approved in the US for this indication, alongside duloxetine and pregabalin.
Used in Antimicrobial Applications:
(1R,2S)-rel-2-(Aminomethyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide hydrochloride also exhibits antibacterial properties, making it a potential candidate for use in the development of new antimicrobial agents to combat bacterial infections.

Biological Activity

Orally active 5-HT and noradrenalin re-uptake inhibitor (SNRI) (IC 50 values are 203 and 100 nM respectively) that displays no affinity at a range of other receptors. Causes adaptive changes to α 1 -adrenergic and 5-HT 2A serotonergic systems when administered repeatedly. Exhibits antidepressive and antinociceptive activities in vivo .

Biochem/physiol Actions

Serotonin and norepinephrine reuptake inhibitor (SNRI)

InChI:InChI=1/C15H22N2O.ClH/c1-3-17(4-2)14(18)15(10-13(15)11-16)12-8-6-5-7-9-12;/h5-9,13H,3-4,10-11,16H2,1-2H3;1H

Upstream product

• 96847-54-0 2-aminomethyl-1-phenyl-N,N-diethylcyclopropanecarboxamide 
• 1353644-50-4 1-phenyl-1-diethylaminocarbonyl-2-chloromethylcyclopropane 
• 96847-54-0 milnacipran 
• 923037-67-6 C₂₂H₂₇NO₄S 
• 22613-99-6 cis-2-Hydroxymethyl-1-phenyl-cyclopropan-1-carbonsaeure 
• 1237261-65-2 (1S,2R)-2-((1,3-dioxoisoindolin-2-yl)methyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide-cyclopropanecarboxamide 
• 74-89-5 methylamine 
• 140-29-4 phenylacetonitrile 
• 174848-98-7 (1S,2R)-2-(azidomethyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide 
• 96847-54-0 (1R,2S)-milnacipran 
• 345349-97-5 (1R,2S)-1-phenyl-2-(azidomethyl)-N,N-diethylcyclopropanecarboxamide 

Relevant articles and documents

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IMPROVED PROCESS FOR THE PREPARATION OF LEVOMILNACIPRAN

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Preparation method of levomilnacipran hydrochloride

The invention relates to the field of chemical medicines and organic synthesis and in particular relates to a preparation method of levomilnacipran hydrochloride. Aiming at solving the problems of anexisting method for preparing the levomilnacipran hydrochloride that the cost is relatively high or a generation process is relatively dangerous so that large-scale industrial production is limited, the preparation method is characterized by comprising the following steps: [1] enabling phenylacetonitrile and (R)-2-chloromethyl ethylene oxide to react under the action of sodium amide to obtain a compound 1; then carrying out hydrolysis cyclization on the compound 1 to obtain a compound 2; [2] enabling the compound 2 and thionyl chloride to react in alcohol, so as to obtain a compound 3; [3] enabling the compound 3 to be subjected to exchange reaction through introducing nitryl and amino, so as to obtain a compound 6; [4] reducing nitryl in the compound 6 and forming salt in situ to obtain the levomilnacipran hydrochloride. The preparation method provided by the invention is applicable to industrial production of the levomilnacipran hydrochloride.

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PROCESS FOR THE PREPARATION OF (1S,2R)-MILNACIPRAN

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