3-ethyl-2-methyl-5-(morpholin-4-ylmethyl)-4,5,6,7-tetrahydro-1H-indol-4-one hydrochloride

• ChemBase ID: 154262
• Molecular Formular: C16H25ClN2O2
• Molecular Mass: 312.8349
• Monoisotopic Mass: 312.16045573
• SMILES: CCc1c([nH]c2c1C(=O)C(CC2)CN1CCOCC1)C.Cl
• Canonical SMILES: CCc1c(C)[nH]c2c1C(=O)C(CC2)CN1CCOCC1.Cl
• InChI: InChI=1S/C16H24N2O2.ClH/c1-3-13-11(2)17-14-5-4-12(16(19)15(13)14)10-18-6-8-20-9-7-18;/h12,17H,3-10H2,1-2H3;1H
• InChIKey: GQWNECFJGBQMBO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-ethyl-2-methyl-5-(morpholin-4-ylmethyl)-4,5,6,7-tetrahydro-1H-indol-4-one hydrochloride
• IUPAC Traditional name: molindone hydrochloride
• Synonyms: 3-ethyl-2-methyl-5-(morpholin-4-ylmethyl)-4,5,6,7-tetrahydro-1H-indol-4-one hydrochloride; 3-Ethyl-1,5,6,7-tetrahydro-2-methyl-5-(4-morpholinylmethyl)-4H-indol-4-one hydrochloride; Molindone hydrochloride; 3-Ethyl-1,5,6,7-tetrahydro-2-methyl-5-(4-morpholinylmethyl)-4H-indol-4-oneHydrochloride; EN 1733A; Lindone; Moban; Molindone Hydrochloride

Database IDs

• CAS Number: 15622-65-8
• MDL Number: MFCD01718304
• PubChem SID: 162248401; 24277995
• PubChem CID: 9883259

CALCULATED PROPERTIES

• Acid pKa: 15.337675
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.8571428
• LogD (pH = 7.4): 1.9640257
• Log P: 2.035115
• Molar Refractivity: 81.0594 cm^3
• Polarizability: 30.793152 Å^3
• Polar Surface Area: 45.33 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; H2O: soluble19 mg/mL; Methanol (Sparingly)
• Apperance: Light Tan Solid; off-white solid
• Melting Point: 195-197°C (dec.)
• Hydrophobicity(logP): 2.572

Safety Information

• Storage Condition: Refrigerator, under inert atmosphere
• RTECS: NM3325000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Gene Information: human ... DRD2(1813), MAOA(4128), MAOB(4129)

Product Information

• Purity: ≥98% (HPLC); 95%
• Empirical Formula (Hill Notation): C16H24N2O2 · HCl

DETAILS

Sigma Aldrich - M1818

Biochem/physiol Actions
D2 dopamine receptor antagonist; MAO inhibitor.

Toronto Research Chemicals - M487500

D2 Dopamine receptor antagonist. MAO inhibitor. Antipsychotic.

REFERENCES

• Sugerman, H., et al.: Clin. Pharmacol. Ther., 8, 261 (1967)
• Claghorn, et al.: Curr. Ther. Res., 11, 524 (1967)
• Goldenthal, E.I., et al.: Toxicol. Appl. Pharmacol., 18, 185 (1967)