Dapoxetine hydrochloride CAS:129938-20-1

  • Product Name:Dapoxetine hydrochloride
  • CAS:129938-20-1
  • Molecular formula:C21H23NO·HCl
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Dapoxetine hydrochloride CAS:129938-20-1

Dapoxetine hydrochloride CAS:129938-20-1 Basic information

Product Name: Dapoxetine hydrochloride
Synonyms: D-Dapoxetine Hydrochloride;(S)-Dapoxetine hydrochloride;Dapoxetine hydrochloride|S1869;Dapoxetine hydrochloride(Priligy);(αS)-N,N-DiMethyl-α-[2-(1-naphthalenyloxy)ethyl]benzeneMethanaMine;(S)-N,N-DIMETHYL-Α-[2-(1-NAPHTHALENY-LOXY)ETHYL]BENZENEMETHANAMINE
CAS: 129938-20-1
MF: C21H23NO·HCl
MW: 341.88
EINECS: 640-411-8
Product Categories: Amines;Aromatics;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Dapoxetine Hydrochloride
Mol File: Mol File

Dapoxetine hydrochloride CAS:129938-20-1 Chemical Properties

Melting point: 175-1790C
form: powder
storage temp.: -20°C Freezer
solubility: DMSO: ≥20mg/mL
Merck: 14,2821
PH: D +135.78° (c = 2.18 in methanol)
alpha: D +135.78° (c = 2.18 in methanol)
optical activity: [α]25/D +23.3 to +24.3°(lit.)
CAS DataBase Reference: 129938-20-1(CAS DataBase Reference)

ITEMS

 

Appeaance

SPECIFICATION

 

White or almost white crystalline powder, light odor

RESULTS

 

Conforms

Identification

IR: Sample IR spectrum must match with that of standard

 

Conforms

 

Solubility

Soluble in methanol and ethanol, some soluble in water

 

Conforms

Specific Rotation

(in 1% methanol)

+125° ~+132°


Melting Range

172-184 °C

1so.3~1s2_5·c

Loss on Drying

≤0.5%

0.22%

Sulfated Ash

≤0.2%

0.1%

Heavy Metals

<20ppm

< 20ppm

Residual Solvents

Ethyl Acetate <5000ppm

316 ppm

 

Related Substances

Max Single Impurity <0.5% 

Total Impurity <1.0%

 

0.49%



99.3%

Conclusion



Dapoxetine hydrochloride Usage And Synthesis
DescriptionPE is the most common form of male sexual dysfunction affecting 20-40% of men globally at some point in their lives. Ejaculation is a reflex comprising different sensory pathways, motor centers, and nerve pathways. This ejaculatory reflex has been shown to be controlled primarily by serotonin and dopamine. Dapoxetine is a short-acting SSRI. It is differentiated from the existing SSRI treatments for PE by the fact that it can be administered on an as-needed basis. In healthy subjects, dapoxetine is rapidly absorbed after oral administration with a peak plasma concentration (Tmax) occurring between 1.4 and 2 h.
Dapoxetine also showed statistically significant improvements in perceived control over ejaculation, PE-related personal distress, and other patient-reported outcomes in all five trials. Dapoxetine treatment was generally well tolerated, with low incidences of discontinuation syndrome, sexual dysfunction, and treatment-emergent mood symptoms. The most common adverse events with dapoxetine included nausea, diarrhea, headache, dizziness, and somnolence.
Chemical PropertiesOff-white Cryst
OriginatorLilly (US)
UsesSelective serotonin reuptake inhibitor (SSRI)
UsesDapoxetine hydrochloride is a short-acting novel selective serotonin reuptake inhibitor marketed for the treatment of premature ejaculation in men. Premature ejaculation (PE) is the most common male sexual disorder, estimated to affect up to 30% of men. D
UsesA selective serotonin reuptake inhibitor
Brand namePriligy
Chemical SynthesisDapoxetine can be synthesized in four chemical steps starting from R-1phenyl- 1,3-propanediol via selective tosylation of the primary hydroxy group with p-toluenesulfonyl chloride, triethylamine and 4-(dimethylamino) pyridine (DMAP), and subsequent condensation with 1naphthol by means of sodium- or lithium hydroxide to yield R-3-(1naphthyloxy)- 1-phenylpropanol as the key intermediate. Conversion of the alcohol group to the corresponding mesylate with methanesulfonyl chloride, triethylamine, and DMAP, followed by treatment with dimethylamine affords dapoxetine, which is then acidified to its hydrochloride salt.


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