Levomilnacipran hydrochloride

Base Information

• Chemical Name: Levomilnacipran hydrochloride
• CAS No.: 101152-94-7
• Molecular Formula: C₁₅H₂₂N₂O*ClH
• Molecular Weight: 282.813
• Hs Code.: 29242990
• European Community (EC) Number: 620-477-4,807-579-6
• UNII: 371U2ZK31U
• DSSTox Substance ID: DTXSID801026201
• Wikidata: Q27256611
• NCI Thesaurus Code: C166646
• RXCUI: 1433211
• ChEMBL ID: CHEMBL2105732
• Mol file: 101152-94-7.mol

Synonyms:Fetzima;levomilnacipran;Levomilnacipran Hydrochloride

Chemical Property of Levomilnacipran hydrochloride

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 1.66E-07mmHg at 25°C
• Melting Point: 179-181 °C
• Boiling Point: 393 °C at 760 mmHg
• Flash Point: 191.5 °C
• PSA: 46.33000
• LogP: 3.27370
• Storage Temp.: 2-8°C
• Solubility.: H2O: 19 mg/mL
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 282.1498911
• Heavy Atom Count: 19
• Complexity: 295

Purity/Quality:

99%MIN ^*data from raw suppliers

Milnacipran hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T,F
• Statements: 22-39/23/24/25-23/24/25-11
• Safety Statements: 7-16-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)C(=O)C1(CC1CN)C2=CC=CC=C2.Cl
• Isomeric SMILES: CCN(CC)C(=O)[C@]1(C[C@H]1CN)C2=CC=CC=C2.Cl
• Recent ClinicalTrials: Effect of F2695 on Brain Activity Measured by Functional Magnetic Resonance Imaging
• Recent EU Clinical Trials: A European Phase III, Multicentre, Double-blind, Randomised, Placebo-Controlled Monotherapy Study of Milnacipran for the Treatment of the Fibromyalgia Syndrome.
• Recent NIPH Clinical Trials: None
• Uses: Antidepressant. A selective norepinephrine and serotonin reuptake inhibitor approved for the management of fibromyalgia. antibacterial

Technology Process of Levomilnacipran hydrochloride

There total 72 articles about Levomilnacipran hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

(1S,2R)-2-(aminomethyl)-N,N-diethyl-1-phenylcyclopropane-1-carboxamide (96847-54-0,92623-85-3,96847-55-1) → (1S,2R)-milnacipran hydrochloride (101152-94-7,175131-61-0)

Guidance literature:

With hydrogenchloride; In water; acetonitrile; Solvent;

Reference yield: 95.0%

C15H20N4O → cis-(±)-1-phenyl-2-(aminomethyl)-N,N-diethylcyclopropanecarboxamide hydrochloride (86181-08-0,101152-94-7,175131-61-0)

Guidance literature:

C₁₅H₂₀N₄O; With palladium 10% on activated carbon; hydrogen; In methanol; for 2h; under 3750.38 Torr;

With hydrogenchloride; In methanol; water;

Reference yield: 94.0%

(1S,2R)-2-((1,3-dioxoisoindolin-2-yl)methyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide-cyclopropanecarboxamide (1237261-65-2) + methylamine (74-89-5) → (1S,2R)-milnacipran hydrochloride (101152-94-7,175131-61-0)

Guidance literature:

(1S,2R)-2-((1,3-dioxoisoindolin-2-yl)methyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide-cyclopropanecarboxamide; methylamine; In 2-methyltetrahydrofuran; water; at 25 ℃; for 3h; Inert atmosphere;

With hydrogenchloride; In methanol; Isopropyl acetate; at 84 - 85 ℃; under 760.051 Torr; pH=1 - 2;

upstream raw materials:

trans-2-aminomethyl-1-phenyl-N,N-diethylcyclopropanecarboxamide

phenylacetonitrile

(1SR,2RS)-2-(chloromethyl)-N,N-diethyl-1-phenylcyclopropane carboxamide

(1SR,2RS)-2-((1,3-dioxoisoindolin-2-yl)methyl)-N,N-diethyl-1-phenylcyclopropane carboxamide

Refernces

• 1、 -. "Drug intermediate as well as preparation and application thereof". Paragraph 0009; 0065-0068. . Retrieved 2021/05/08.
• 2、 -. "Preparation of leveminacipran hydrochloride". Paragraph 0015-0019. . Retrieved 2020/06/16.