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

• 321-38-0 1-Fluoronaphthalene 
• 116539-55-0 (S)-3-methylamino-1-(2-thienyl)-1-propanol 
• 597581-32-3 (S)-N-BOC-duloxetine 
• 5424-47-5 3-(dimethylamino)-1-(thiophen-2-yl)propan-1-one hydrochloride 
• 116817-13-1 duloxetine 
• 13636-02-7 3-(N,N-dimethylamino)-1-(thien-2-yl)propan-1-ol 
• 132335-44-5 (S)-3-dimethylamino-1-(2-thienyl)propan-1-ol 
• 88-15-3 2-Acetylthiophene 
• 597581-31-2 (3-hydroxy-3-thiophen-2-yl-propyl)-methyl-carbamic acid tert-butyl ester 
• 597581-29-8 ((S)-3-Hydroxy-3-thiophen-2-yl-propyl)-carbamic acid ethyl ester 
• 597581-30-1 (R)-(3-hydroxy-3-thiophen-2-yl-propyl)carbamic acid ethyl ester 
• 597581-26-5 (R)-2-cyano-1-(thiophen-2-yl)ethyl acetate 
• 597581-28-7 (S)-2-cyano-1-(thiophen-2-yl)ethyl acetate 
• 116539-57-2 (R)-3-(methylamino)-1-(thiophen-2-yl)propan-1-ol 

Downstream Products

• 116817-86-8 (+)-(S)-N-methyl-γ-(1-naphthyloxy)-2-thiophenepropylamine maleate 
• 136434-34-9 duloxetine hydrochloride 
• 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)

Chemoenzymatic synthesis of (S)-duloxetine using carbonyl reductase from Rhodosporidium toruloides

A chemoenzymatic strategy was developed for (S)-duloxetine production employing carbonyl reductases from newly isolated Rhodosporidium toruloides into the enantiodetermining step. Amongst the ten most permissive enzymes identified, cloned, and overexpressed in Escherichia coli, RtSCR9 exhibited excellent activity and enantioselectivity. Using co-expressed E. coli harboring both RtSCR9 and glucose dehydrogenase, (S)-3-(dimethylamino)-1-(2-thienyl)-1-propanol 3a was fabricated with so far the highest substrate loading (1000 mM) in a space-time yield per gram of biomass (DCW) of 22.9 mmol L-1 h-1 g DCW-1 at a 200-g scale. The subsequent synthetic steps from RtSCR9-catalyzed (S)-3a were further performed, affording (S)-duloxetine with 60.2% overall yield from 2-acethylthiophene in >98.5% ee.