Dapoxetine hydrochloride

Dapoxetine hydrochloride Basic information
Product Name:Dapoxetine hydrochloride
Synonyms:Dapoxetine hydrochloride (1S)-N,N-Dimethyl-3-naphthalen-1-yloxy-1-phenyl-propan-1-amine hydrochloride;S-(+)-N,N-dimethyl-a-[2-(naphthalenyloxy)ethyl] benzenemethanamine hydrochloride, LY-210448 hydrochloride;Mixed spin Dapoxetine;(1s)-n,n-dimethyl-3-naphthalen-1-yloxy-1-phenyl-propan-1-amine hydrochloride;Rimonabant 75000;(aS)-N,N-Dimethyl-a-[2-(1-naphthalenyloxy)ethyl]benzenemethanamine;LY-21044;((S)-(+)-N,N-Dimethyl-1-phenyl-3-(1-naphthalenyloxy)propanamine hydrochloride)
CAS:129938-20-1
MF:C21H24ClNO
MW:341.88
EINECS:640-411-8
Product Categories:Amines;Aromatics;Inhibitors;Dapoxetine Hydrochloride;Intermediates & Fine Chemicals;Pharmaceuticals;API;129938-20-1
Mol File:129938-20-1.mol
Dapoxetine hydrochloride Structure
Dapoxetine hydrochloride Chemical Properties
Melting point 175-1790C
alpha D +135.78° (c = 2.18 in methanol)
storage temp. room temp
solubility DMSO: ≥20mg/mL
form powder
color white
optical activity[α]/D +125 to +135°, c = 1 in methanol
Merck 14,2821
InChIInChI=1/C21H23NO.ClH/c1-22(2)20(18-10-4-3-5-11-18)15-16-23-21-14-8-12-17-9-6-7-13-19(17)21;/h3-14,20H,15-16H2,1-2H3;1H/t20-;/s3
InChIKeyIHWDIQRWYNMKFM-OZYVVJTJNA-N
SMILESO(C1=CC=CC2C=CC=CC1=2)CC[C@@H](C1C=CC=CC=1)N(C)C.Cl |&1:13,r|
CAS DataBase Reference129938-20-1(CAS DataBase Reference)
Safety Information
Hazard Codes Xn,N
Risk Statements 22-36-50/53
Safety Statements 36-60-61
RIDADR UN 3077 9 / PGIII
WGK Germany 3
HS Code 29221990
MSDS Information
Dapoxetine hydrochloride Usage And Synthesis
DescriptionDapoxetine hydrochloride, belonging to the class of SSRIs, was the first drug originally approved for the on-demand treatment of men with PE by seven European countries in 2008.
Premature ejaculation (PE) is the most common male sexual dysfunction. 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 2h.
Chemical PropertiesDapoxetine hydrochloride is a white to slightly yellow powder. It is freely soluble in methanol, propylene glycol, some organic solvents (eg. N,N-dimethylformamide) , slightly soluble in ethanol and almost insoluble in water. It is a BCSI class II compound, and poor solubility is a key factor affecting the difference in clinical efficacy. Dapoxetine hydrochloride exists in various crystal forms, the solubility of different crystal forms is quite different, and there is a phenomenon of phase and transformation between crystal forms.
OriginatorLilly (US)
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.
Brand namePriligy
General DescriptionDapoxetine ((+)-(S)-N,N-dimethyl-(α)-[2(1naphthal enyloxy)ethyl]-benzenemethanamine hydrochloride) possess a similar structure as that of fluoxetine.
Biochem/physiol ActionsPotent Selective serotonin reuptake inhibitor (SSRI); used in treatment of premature ejaculation
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.
storageroom temperature (desiccate)
Mode of actionThe mechanism of action of dapoxetine in premature ejaculation is presumed to be linked to the inhibition of neuronal reuptake of serotonin and the subsequent potentiation of the neurotransmitter's action at pre- and post-synaptic receptors. Dapoxetine is a centrally-acting SSRI that modulates serotonin levels in relevant areas such as the lateral paragigantocellular nucleus through inhibition of the serotonin transporter (SERT). This compound also decreases peak amplitude and accelerates the decay rate of current inactivation in a variety of voltage-gated K+ channels.
Dapoxetine hydrochloride Preparation Products And Raw materials
(S)-Azelastine Hydrochloride Dyclonine hydrochloride Chlorodimethylphenylsilane Naphthalene Dimethyldimethoxysilane Topotecan hydrochloride Rimonabant ETHANE Dapoxetine Phenyltriethoxysilane Phenacetin 1-Phenylpropan-1-amine Dimethyl fumarate Dapoxetine hydrochloride Phenyltrimethoxysilane Dimethyl sulfoxide (RS)-N-Methyl-gama-(1-naphthalenyloxy)-2-thiophenepropanamine hydrochloride Duloxetine

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