N-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethane-1-sulfonamide hydrochloride

• ChemBase ID: 154588
• Molecular Formular: C17H26ClN3O2S
• Molecular Mass: 371.92524
• Monoisotopic Mass: 371.14342577
• SMILES: CNS(=O)(=O)CCc1ccc2c(c1)c(c[nH]2)C1CCN(CC1)C.Cl
• Canonical SMILES: CNS(=O)(=O)CCc1ccc2c(c1)c(c[nH]2)C1CCN(CC1)C.Cl
• InChI: InChI=1S/C17H25N3O2S.ClH/c1-18-23(21,22)10-7-13-3-4-17-15(11-13)16(12-19-17)14-5-8-20(2)9-6-14;/h3-4,11-12,14,18-19H,5-10H2,1-2H3;1H
• InChIKey: AWEZYKMQFAUBTD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethane-1-sulfonamide hydrochloride
• IUPAC Traditional name: naratriptan hydrochloride
• Synonyms: N-Methyl-2-[3-(1-methyl-4-piperidyl)-1H-indol-5-yl]ethanesulfonamide Hydrochloride; Naramig; Naratriptan Hydrochloride; Amerge; GR-85548A; N-Methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide hydrochloride; Naratriptan hydrochloride

Database IDs

• CAS Number: 143388-64-1
• MDL Number: MFCD08141821
• PubChem SID: 162248726
• PubChem CID: 60875

CALCULATED PROPERTIES

• Acid pKa: 11.549356
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.8418646
• LogD (pH = 7.4): -0.34287214
• Log P: 1.440625
• Molar Refractivity: 94.2572 cm^3
• Polarizability: 38.131832 Å^3
• Polar Surface Area: 65.2 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; H2O: ≥10 mg/mL; Methanol
• Apperance: Beige Solid; white to off-white powder
• Melting Point: 234-236°C

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C17H25N3O2S ·HCl

DETAILS

Sigma Aldrich - N1415

Biochem/physiol Actions
Naratriptan hydrochloride is a serotonin 5-HT1B/1D receptor agonist.

Toronto Research Chemicals - N378730

It is a triptan drug and is used for the treatment of migraine headaches.

REFERENCES

• Dulery, B.D., et al.: J. Pharm. Biomed. Anal., 15, 1009 (1997)
• Havanka, H., et al.: Clin. Ther., 22, 970 (1997)