8-methyl-8-azabicyclo[3.2.1]octan-3-yl 1H-indole-3-carboxylate hydrochloride

• ChemBase ID: 132624
• Molecular Formular: C17H21ClN2O2
• Molecular Mass: 320.81384
• Monoisotopic Mass: 320.1291556
• SMILES: CN1C2CCC1CC(C2)OC(=O)c1c[nH]c2c1cccc2.Cl
• Canonical SMILES: CN1C2CCC1CC(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
• InChIKey: XIEGSJAEZIGKSA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-methyl-8-azabicyclo[3.2.1]octan-3-yl 1H-indole-3-carboxylate hydrochloride
• IUPAC Traditional name: 8-methyl-8-azabicyclo[3.2.1]octan-3-yl 1H-indole-3-carboxylate hydrochloride
• Synonyms: 3-Tropanylindole-3-carboxylate monohydrochloride; ICS-205,930; Navoban; Tropisetron monohydrochloride; 1H-Indole-3-carboxylic Acid (3-endo)-8-Methyl-8-azabicyclo[3.2.1]oct-3-yl Ester Hydrochloride; Novaban; SDZ-ICS 930; Tropisetron Hydrochloride; endo-8-Methyl-8-azabicyclo[3.2.1]oct-3-ol Indol-3-yl-carboxylate 盐酸盐; Tropisetron

Database IDs

• CAS Number: 105826-92-4
• MDL Number: MFCD00210221
• PubChem SID: 24278133; 162226901
• PubChem CID: 9818540

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

Physical Property

• Solubility: H2O: >10 mg/mL; Methanol; Water
• Apperance: solid; White to Off-White Solid
• Melting Point: 283-285°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... CHRNA3(1136), CHRNA4(1137), CHRNB2(1141), CHRNB4(1143), HTR3A(3359), HTR3B(9177), HTR3C(170572), HTR3D(200909), HTR3E(285242)rat ... Chrna7(25302), Drd2(24318), Htr1a(24473), Htr3a(79246)

Product Information

• Purity: ≥98% (HPLC)

DETAILS

Sigma Aldrich - T104

Biochem/physiol Actions
3-Tropanylindole-3-carboxylate hydrochloride is a selective 5-HT3 serotonin receptor antagonist.
Tropisetron a selective serotonin 5-HT3 receptor antagonist is used mainly as an antiemetic to treat nausea and vomiting following chemotherapy . In the treatment of fibromyalgia syndrome (FMS) tropisetron reduced not only pain perception but also had a favourable effect on cardiac dysfunction during treatment.

Toronto Research Chemicals - T892700

Specific serotonin (5-HT3) receptor antagonist. Antiemetic.

REFERENCES

• Richardson, B.P., et al.: Nature, 316, 126 (1985)
• Williams, F.M., et al.: J. Cardiovasc. Pharmacol., 7, 550 (1985)
• Waeber, C., et al.: Neuroscience, 31, 393 (1985)
• Seynaeve, C., et al.: Anti-Cancer Drugs, 2, 343 (1985)
• Fischer, V., et al.: Dug Metab.