116539-60-7

Basic information

• Product Name: (R)-Duloxetine
• Synonyms: (r)-duloxetine;(r)-n-methyl-gama-(1-naphthalenyloxy)-2-thiophenepropanamine;R-DULOXETINE HCL;(R)-N-Methyl-3-(naphthalen-1-yloxy)-3-(thiophen-2-yl)propan-1-aMine hydrochloride;Duloxetine hydrochloride impurity A -G;Duloxetine hydrochloride impurity A;(R)-Doluxitine;R-DULOXETINE Oxalate
• CAS NO: 116539-60-7
• Molecular Formula: C₁₈H₁₉NOS
• Molecular Weight: 333.881
• EINECS: 1312995-182-4
• Product Categories: Pharmaceutical intermediate
• Mol File: 116539-60-7.mol
• Article Data: 67

Chemical Properties

• Boiling Point: 466.2 °C at 760 mmHg
• Flash Point: 235.7 °C
• Appearance: /
• Density: 1.158
• Vapor Pressure: 7.23E-09mmHg at 25°C
• Refractive Index: 1.627
• PKA: 10.02±0.10(Predicted)
• CAS DataBase Reference: (R)-Duloxetine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-Duloxetine(116539-60-7)
• EPA Substance Registry System: (R)-Duloxetine(116539-60-7)

Safety Data

• Hazardous Substances Data: 116539-60-7(Hazardous Substances Data)

Usage

General Description

"(R)-Duloxetine" is the R-enantiomer of the drug duloxetine, which is a selective serotonin and norepinephrine reuptake inhibitor (SNRI) used for the treatment of depression, anxiety, nerve pain, and fibromyalgia. As an enantiomer, it has a specific three-dimensional arrangement of atoms that gives it distinct pharmacological properties compared to its S-enantiomer. (R)-Duloxetine works by increasing the levels of serotonin and norepinephrine in the brain, which can help improve mood, alleviate pain, and reduce anxiety. It is prescribed in capsule form for oral administration and is generally well-tolerated, although it may cause side effects such as nausea, dry mouth, dizziness, and drowsiness.

InChI:InChI=1/C18H19NOS/c1-19-12-11-17(18-10-5-13-21-18)20-16-9-4-7-14-6-2-3-8-15(14)16/h2-10,13,17,19H,11-12H2,1H3/t17-/m1/s1

Upstream product

• 878757-08-5 (R)-(-)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propylamine 
• 321-38-0 1-Fluoronaphthalene 
• 116539-57-2 (R)-3-(methylamino)-1-(thiophen-2-yl)propan-1-ol 
• 33898-90-7 2-Thenoylacetonitrile 
• 858130-53-7 (R)-3-amino-1-(thiophen-2-yl)propan-1-ol 
• 597581-30-1 (R)-(3-hydroxy-3-thiophen-2-yl-propyl)carbamic acid ethyl ester 
• 29683-77-0 2-chloro-1-(thiophen-2-yl)ethanone 
• 49703-01-7 2-(1-hydroxy-2-chloroethyl)-thiophene 
• 235085-83-3 (±)-3-hydroxy-3-(thiophen-2-yl)propanenitrile 
• 524047-48-1 (R)-3-hydroxy-3-(thiophen-2-yl)propanenitrile 
• 597581-26-5 (R)-2-cyano-1-(thiophen-2-yl)ethyl acetate 
• 88-15-3 2-Acetylthiophene 
• 5424-47-5 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride 
• 132335-49-0 α-[2-(dimethylamino)ethyl](thiophene-2-yl)methanol 

Downstream Products

• 116817-86-8 (+)-(S)-N-methyl-γ-(1-naphthyloxy)-2-thiophenepropylamine maleate 
• 136434-34-9 duloxetine hydrochloride 
• 959392-22-4 (S)-(+)-N-methyl-3-(1-naphthalenyloxy)-3-(3-thienyl)propanamine 
• 116817-13-1 duloxetine 
• 910138-96-4 (R)-(-)-N-methyl-3-(1-napthalenyloxy)-3-(2-thienyl)propanamine hydrochloride 
• 132335-46-7 N-methyl-(S)-duloxetine 
• 1309349-73-2 ketorolac (S)-duloxetine salt 
• 1309349-74-3 nimesulide (S)-duloxetine salt 
• 1309349-83-4 diclofenac (S)-duloxetine salt 
• 1309349-71-0 acemetacin (S)-duloxetine salt 
• 1309349-90-3 sulindac (S)-duloxetine salt 
• 1033719-36-6 2-(1-(2-hydroxynaphth-1-yl)-3-(methylamino)propyl)-thiophene hydrochloride 
• 953028-76-7 2-(1-(4-hydroxynaphth-1-yl)-3-(methylamino)propyl)-thiophene hydrochloride 

Relevant articles and documents

Preparation method of duloxetine

To the method, 1 - naphthol and 3 - (2 - thienyl) -2 - acrolein serve as starting materials, and (S)-3 - (1 - naphthyloxy) -3 - (2 - thienyl) propanal is obtained through addition reaction under the action of a catalyst. The raw materials are cheap and easily available, and 1 - fluoronaphthalene which is expensive is not needed. Sodium hydride and operation are tedious, the cost is low, the process operation is safe and convenient, the three wastes are small in generation amount, and green and environment-friendly. The reaction atom economy is high, the reaction selectivity of each step is high, the side reaction is small, the optical purity and yield of the target product are high, and the green industrial production is facilitated.

Duloxetine hydrochloride salt of basic and duloxetine (by machine translation)

[Problem] to suppress toxic byproducts, and suppressing the formation of decomposition products of high purity optical isomers as well as the method for manufacturing a basic duloxetine hydrochloride duloxetine. [Solution] a basic manufacturing method of duloxetine, [...], potassium hydroxide and toluene in the presence of alcohol in the mixing step, and, by heating the reaction mixture obtained, comprising the step of distilling off the solvent in the reaction portion, a basic manufacturing method of duloxetine. [Drawing] no (by machine translation)

Method for the synthesis of duloxetine

A synthetic method of duloxetine is as below: reacting water, tetrahydrofuran or dioxane, 1-chloro ethyl-N-methyl-((S)-3-(naphthalene-1-phenoxy)-3-(thiophene-2-yl) propyl) carbamate and alkali at a reflux temperature of 20 DEG C, preferably 50 DEG C; after the reaction, condensing a reaction liquid; and adding another organic solvent for extraction, so as to obtain a solution containing dutoxetine. Compared with the existing method for preparing duloxetine, the method overcomes the disadvantages of long reaction time or high reaction temperature, high energy consumption, long production cycle, low yield, a large amount of industrial waste water difficult to process, harm to the environment, flammable and explosive reagents and huge security hidden trouble, and has the advantages of low reaction temperature, short reaction time, a small amount of produced industrial waste liquid, greenness, environment-friendliness, high safety, and suitability for large-scale industrial production of duloxetine.