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

• ChemBase ID: 36038
• Molecular Formular: C11H12N2
• Molecular Mass: 172.22638
• Monoisotopic Mass: 172.10004839
• SMILES: c1ccc2[nH]c3c(c2c1)CCNC3
• Canonical SMILES: N1CCc2c(C1)[nH]c1c2cccc1
• InChI: InChI=1S/C11H12N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-4,12-13H,5-7H2
• InChIKey: CFTOTSJVQRFXOF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1H,2H,3H,4H,9H-pyrido[3,4-b]indole
• IUPAC Traditional name: tryptoline; 1H,2H,3H,4H,9H-pyrido[3,4-b]indole
• Synonyms: THBC; Tetrahydronorharmane; Tryptoline; 1,2,3,4-Tetrahydro-9H-pyrido[3,4-b]indole; 2,3,4,9-Tetrahydro-1H-beta-carboline; 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole; Noreleagnine; Tetrahydronorharman; 2,3,4,9-Tetrahydro-1H-β-carboline; Tryptoline; Tetrahydronorharman; 1,2,3,4-Tetrahydro-9H-pyrido[3,4-b]indole; 1,2,3,4-Tetrahydronorharman; Tetrahydronorharman, THBC; 1,2,3,4-Tetrahydro-β-carboline; 1,2,3,4-四氢-β-咔啉; 2,3,4,9-四氢-1H-吡啶并(3,4-b)吲哚; 1,2,3,4-四氢-9H-吡啶并[3,4-b]吲哚

Database IDs

• CAS Number: 16502-01-5
• MDL Number: MFCD00004954
• PubChem SID: 160999345; 24857939
• PubChem CID: 107838
• CHEMBL: 269236
• Chemspider ID: 96979
• Wikipedia Title: Tryptoline

CALCULATED PROPERTIES

• Acid pKa: 16.456234
• H Acceptors: 1
• H Donor: 2
• LogD (pH = 5.5): -1.4649161
• LogD (pH = 7.4): -0.021349961
• Log P: 1.5902463
• Molar Refractivity: 53.5796 cm^3
• Polarizability: 21.865826 Å^3
• Polar Surface Area: 27.82 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 10mg/mL in 1N Ammonium Hydroxide in Methanol; DMSO
• Apperance: Tan Solid
• Melting Point: 206-208 °C(lit.); 206-208°C

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: IRRITANT
• 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: Competitive selective inhibitors of monoamine oxidase type a (MAO-A); Potent reuptake inhibitors of 5-hydroxytryptamine and epinephrine; Sympatholytic-alpha

Product Information

• Purity: 98%
• Application(s): Sympatholytic
• Empirical Formula (Hill Notation): C11H12N2

DETAILS

Sigma Aldrich - 300764

Packaging
1, 5 g in glass bottle
Application

• Reactant for synthesis of the indolyl-β-carboline alkaloid eudistomin U via IBX mediated room temperature oxidative aromatization1
• Reactant for preparation of neuroprotective HDAC6 inhibitors2
• Reactant for preparation of aminofuranopyrimidines as EGFR and Aurora A kinase inhibitors3
• Reactant for preparation of inhibitors of CDK44
• Reactant for preparation of tetrahydrocarboline derivatives of as human 5-HT5A receptor ligands5
• Reactant for preparation of 5-(diaminomethyl)-2,4-aminopyrimidines as dihydrofolate reductase inhibitors and antibacterial agents6
Employed in alkaloid synthesis and in studies on neurodegenerative diseases.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 300764.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - T293250

A mitotic kinesin inhibitor as novel anti-cancer agent. Used in the study of neurodegenerative diseases.

REFERENCES

• Brown, K., et al.: J. Cell Biol., 125, 1303 (1994)
• Sharp, D., et al.: Nature, 407, 41 (1994)
• Sueishi, M., et al.: J. Biol. Chem., 275, 28888 (1994)
• Lee, Y., et al.: Biochem. J., 360, 549 (1994)