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Merck
CN

D7071

Sigma-Aldrich

Dapoxetine hydrochloride

≥98% (HPLC)

Synonym(s):

(S)-N,N-dimethyl-1-phenyl-3-(1-naphthalenyloxy)propanamine hydrochloride, S-(+)-N,N-dimethyl-a-[2-(naphthalenyloxy)ethyl] benzenemethanamine hydrochloride, LY-210448 hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C21H23NO · HCl
CAS Number:
129938-20-1
Molecular Weight:
341.87
MDL number:
MFCD08272809
UNSPSC Code:
12352200
PubChem Substance ID:
329798842
NACRES:
NA.77

Key Documents

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Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +125 to +135°, c = 1 in methanol

storage condition

desiccated

color

white

solubility

DMSO: ≥20 mg/mL

originator

Eli Lilly

storage temp.

room temp

SMILES string

Cl.CN(C)[C@@H](CCOc1cccc2ccccc12)c3ccccc3

InChI

1S/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-;/m0./s1

InChI key

IHWDIQRWYNMKFM-BDQAORGHSA-N

Gene Information

human ... SLC6A4(6532)

General description

Dapoxetine ((+)-(S)-N,N-dimethyl-(α)-[2(1naphthal enyloxy)ethyl]-benzenemethanamine hydrochloride) possess a similar structure as that of fluoxetine.

Biochem/physiol Actions

Dapoxetine is capable of blocking recombinant Kv4.3 potassium voltage-gated channels. It is considered as safe.
Potent Selective serotonin reuptake inhibitor (SSRI); used in treatment of premature ejaculation
Potent and selective SSRI

Features and Benefits

This compound is featured on the Biogenic Amine Transporters page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Eli Lilly. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H319,H413

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 4 - Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000362275
0000362275
0000257055
0000250041
0000257055

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Imju Jeong et al.
Neuropharmacology, 62(7), 2261-2266 (2011-12-24)
Dapoxetine, a short-acting selective serotonin reuptake inhibitor, is widely prescribed for the treatment of patients with premature ejaculation. The effects of dapoxetine were examined on cloned Kv4.3 channels stably expressed in Chinese hamster ovary cells using the whole-cell patch-clamp technique.
Chris G McMahon
Expert opinion on pharmacotherapy, 11(10), 1741-1752 (2010-06-15)
Premature ejaculation (PE) is a common male sexual disorder which is associated with substantial personal and interpersonal negative psychological factors. Drug treatment of PE with an off-label antidepressant selective serotonin reuptake inhibitor (SSRI) drug is common. The lack of an
Chris G McMahon et al.
The journal of sexual medicine, 8(10), 2707-2725 (2011-07-21)
New diagnostic criteria for lifelong premature ejaculation (PE) have been proposed by the International Society of Sexual Medicine (ISSM), including an intravaginal ejaculatory latency time (IELT) of less than about 1 minute, lack of control over ejaculation, and PE-related distress
Ahmed A Abu-Hassan et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 239, 118512-118512 (2020-05-30)
One of the medical problems is premature ejaculation which characterized by quick ejaculation and reaching orgasm rapidly. Dapoxetine was accepted as off-label antidepressant used in the treatment of premature ejaculation, so hereby we provide an innovative, non-extractive, environmentally safe protocol
Hartmut Porst
The journal of sexual medicine, 8 Suppl 4, 335-341 (2011-10-14)
With increasing interest and clinical research in male sexual disorders, it has become clear that not only psychological but also organic, neurobiological, and genetic factors may play an important role in premature ejaculation (PE). This article provides an overview of
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