6-methoxy-1H,2H,3H,4H,9H-pyrido[3,4-b]indole

• ChemBase ID: 37473
• Molecular Formular: C12H14N2O
• Molecular Mass: 202.25236
• Monoisotopic Mass: 202.11061308
• SMILES: c1(ccc2c(c1)c1c([nH]2)CNCC1)OC
• Canonical SMILES: COc1ccc2c(c1)c1CCNCc1[nH]2
• InChI: InChI=1S/C12H14N2O/c1-15-8-2-3-11-10(6-8)9-4-5-13-7-12(9)14-11/h2-3,6,13-14H,4-5,7H2,1H3
• InChIKey: QYMDEOQLJUUNOF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-methoxy-1H,2H,3H,4H,9H-pyrido[3,4-b]indole
• IUPAC Traditional name: 6-methoxy-1H,2H,3H,4H,9H-pyrido[3,4-b]indole
• Synonyms: 6-Methoxy-2,3,4,9-tetrahydro-1H-beta-carboline; 6-Methoxy-1,2,3,4-tetrahydro-β-carboline; 6-Methoxy-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole; Methoxytetrahydro-beta-carboline; 6-Methoxytryptoline; Pinoline

Database IDs

• CAS Number: 20315-68-8
• MDL Number: MFCD00012071
• PubChem SID: 161000780; 24278180
• PubChem CID: 1868

CALCULATED PROPERTIES

• Acid pKa: 16.731968
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -1.6311463
• LogD (pH = 7.4): -0.2028032
• Log P: 1.432575
• Molar Refractivity: 60.0428 cm^3
• Polarizability: 24.326248 Å^3
• Polar Surface Area: 37.05 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 219-222 °C(lit.)

Safety Information

• Storage Warning: IRRITANT
• RTECS: UV0725000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: rat ... Htr2a(29595), Htr2c(25187)
• Mechanism of Action: CNS stimulant; Monoamine oxidase inhibitor

Product Information

• Purity: 97%
• Biological Source: Alkaloid from Desmodium pulchellum (Leguminosae)
• Application(s): Antiparkinsonic
• Empirical Formula (Hill Notation): C12H14N2O

DETAILS

Sigma Aldrich - 291552

Packaging
100, 500 mg in glass bottle

REFERENCES

• Audette, R.C.S. et al., Can. J. Chem., 1970, 48, 149, (isol, uv, ir, pmr, ms)
• Ghosal, S., Planta Med., 1972, 21, 200, (deriv)
• Filho, D. dos S. et al., Phytochemistry, 1975, 14, 821, (isol, uv, ir, pmr, ms)
• Slaviik, J. et al., Coll. Czech. Chem. Comm., 1976, 41, 3343; 1977, 42, 132; 1978, 43, 316, (isol, uv, ir)
• Baudouin, G. et al., J. Nat. Prod., 1981, 44, 546, (isol, deriv)