dimethyl[(1S)-3-(naphthalen-1-yloxy)-1-phenylpropyl]amine hydrochloride

• ChemBase ID: 70172
• Molecular Formular: C21H24ClNO
• Molecular Mass: 341.87436
• Monoisotopic Mass: 341.15464207
• SMILES: [C@@H](CCOc1cccc2ccccc12)(N(C)C)c1ccccc1.Cl
• Canonical SMILES: CN([C@H](c1ccccc1)CCOc1cccc2c1cccc2)C.Cl
• InChI: 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
• InChIKey: IHWDIQRWYNMKFM-BDQAORGHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: dimethyl[(1S)-3-(naphthalen-1-yloxy)-1-phenylpropyl]amine hydrochloride
• IUPAC Traditional name: dapoxetine hydrochloride
• Synonyms: (S)-N,N-Dimethyl-3-(naphthalen-1-yloxy)-1-phenylpropan-1-amine hydrochloride; Priligy; LY-210448 hydrochloride; Dapoxetine hydrochloride; S1869; (αS)-N,N-Dimethyl-α-[2-(1-naphthalenyloxy)ethyl]benzenemethanamine; LY-210448; (S)-N,N-dimethyl-1-phenyl-3-(1-naphthalenyloxy)propanamine hydrochloride; S-(+)-N,N-dimethyl-a-[2-(naphthalenyloxy)ethyl] benzenemethanamine hydrochloride, LY-210448 hydrochloride; Dapoxetine hydrochloride

Database IDs

• CAS Number: 129938-20-1
• MDL Number: MFCD08272809
• PubChem SID: 162035896
• PubChem CID: 71352

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.4468201
• LogD (pH = 7.4): 3.020529
• Log P: 4.667896
• Molar Refractivity: 96.1387 cm^3
• Polarizability: 39.01058 Å^3
• Polar Surface Area: 12.47 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO: ≥20 mg/mL; Methanol
• Apperance: white powder; White to Off-White Solid
• Melting Point: 180-182°C
• Optical Rotation: [α]/D +125 to +135°, c = 1 in methanol

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• Storage Warning: IRRITANT
• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36-50/53
• Safety Statements: 36-60-61
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H319-H413
• GHS Precautionary statements: P305 + P351 + P338
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC); 95+%
• Salt Data: HCL
• Empirical Formula (Hill Notation): C21H23NO · HCl

DETAILS

Selleck Chemicals - S1869

Research Area: Neurological Disease
Biological Activity:
Dapoxetine 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. Dapoxetine is the only drug with regulatory approval for such an indication. The treatment of PE consists of primarily off-label use of oral selective serotonin reuptake inhibitors (SSRIs) via either on-demand or daily delivery. [1][2]

Sigma Aldrich - D7071

Biochem/physiol Actions
Potent Selective serotonin reuptake inhibitor (SSRI); used in treatment of premature ejaculation

Toronto Research Chemicals - D185700

Selective serotonin reuptake inhibitor (SSRI).

REFERENCES

• Kendirci M et al. Ther Clin Risk Manag. 2007 Jun
• Feret, B., et al.: Formulary, 40, 227 (2005)