(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 1H-indole-3-carboxylate hydrochloride

• ChemBase ID: 120167
• Molecular Formular: C17H21ClN2O2
• Molecular Mass: 320.81384
• Monoisotopic Mass: 320.1291556
• SMILES: c1(C(=O)O[C@@H]2C[C@@H]3N([C@H](C2)CC3)C)c[nH]c2c1cccc2.Cl
• Canonical SMILES: CN1[C@@H]2CC[C@H]1C[C@@H](C2)OC(=O)c1c[nH]c2c1cccc2.Cl
• InChI: InChI=1S/C17H20N2O2.ClH/c1-19-11-6-7-12(19)9-13(8-11)21-17(20)15-10-18-16-5-3-2-4-14(15)16;/h2-5,10-13,18H,6-9H2,1H3;1H/t11-,12+,13+
• InChIKey: XIEGSJAEZIGKSA-LUNMCBQDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 1H-indole-3-carboxylate hydrochloride
• IUPAC Traditional name: (1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 1H-indole-3-carboxylate hydrochloride
• Synonyms: (1R,3r,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 1H-indole-3-carboxylate hydrochloride; Tropisetron Hydrochloride

Database IDs

• CAS Number: 105826-92-4
• PubChem SID: 162214520
• PubChem CID: 656664

CALCULATED PROPERTIES

• Acid pKa: 12.182885
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.70924056
• LogD (pH = 7.4): 0.69646686
• Log P: 2.6276226
• Molar Refractivity: 81.5023 cm^3
• Polarizability: 32.93648 Å^3
• Polar Surface Area: 45.33 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: 5HT3-Receptor antagonist

Product Information

• Salt Data: HCl
• Application(s): Used as an emetic for the control of nausea during chemotherapy

REFERENCES

• Ger. Pat., 1983, 3 322 574; CA, 100, 209629q, (synth)
• Coker, S.J. et al., Eur. J. Pharmacol., 1986, 127, 211, (metab)
• Cestall, B. et al., Neuropharmacology, 1986, 25, 959
• Leibundgut, U. et al., Lancet, 1987, 1198
• Cohen, M.L. et al., J. Pharmacol. Exp. Ther., 1989, 248, 197, (pharmacol)
• Simpson, K. et al., Drugs, 2000, 59, 1297-1315, (rev)