CAS 16502-01-5|tryptoline|1H,2H,3H,4H,9H-pyrido[3,4-b]indole|2,3,4,9-Tetrahydro-1H-beta-carboline|Tetrahydronorharman|1H,2H,3H,4H,9H-pyrido[3,4-b]indole|2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole|1,2...

General Information

Structure

Molecular Formula

C₁₁H₁₂N₂

Molecular Mass

172.22638

Exact Mass

172.10004839

Charge

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

Canonic Smiles

N1CCc2c(C1)[nH]c1c2cccc1

Isomeric Smiles

c1ccc2[nH]c3c(c2c1)CCNC3

Calculated Properties

JChem

Acid pKa

16.456234

H Acceptors

H Donor

LogD (pH = 5.5)

-1.4649161

LogD (pH = 7.4)

-0.021349961

Log P

1.5902463

Molar Refractivity

53.5796

Polarizability

21.865826

Polar Surface Area

27.82

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC Traditional name

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

IUPAC name

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

Synonyms

2,3,4,9-Tetrahydro-1H-beta-carbolineTetrahydronorharman2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole1,2,3,4-Tetrahydro-9H-pyrido[3,4-b]indole2,3,4,9-四氢-1H-吡啶并(3,4-b)吲哚1,2,3,4-四氢-9H-吡啶并[3,4-b]吲哚Tetrahydronorharman2,3,4,9-Tetrahydro-1H-β-carbolineTryptolineTHBCNoreleagnineTryptoline1,2,3,4-四氢-β-咔啉Tetrahydronorharmane1,2,3,4-Tetrahydro-β-carboline1,2,3,4-Tetrahydro-9H-pyrido[3,4-b]indoleTetrahydronorharman, THBC1,2,3,4-Tetrahydronorharman

Names and Identifiers

Registration numbers

CAS Number

MDL Number

PubChem CID

PubChem SID

Chemspider ID

Wikipedia Title

CHEMBL

Registration numbers

Properties

Product Information

Purity

98%

Empirical Formula (Hill Notation)

C11H12N2

Certificate of Analysis

Download link

Application(s)

Sympatholytic

Pharmacology Properties

Gene Information

rat ... Htr2a(29595), Htr2c(25187)

Mechanism of Action

Potent reuptake inhibitors of 5-hydroxytryptamine and epinephrine

Competitive selective inhibitors of monoamine oxidase type a (MAO-A)

Sympatholytic-alpha

Physical Property

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Wikipedia

Tryptoline

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.

TRC

T293250

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

Molecule Details

References

PubChem Literature

From Data Sources

• Lee, Y., et al.: Biochem. J., 360, 549 (1994)

• Sharp, D., et al.: Nature, 407, 41 (1994)

• Brown, K., et al.: J. Cell Biol., 125, 1303 (1994)

• Sueishi, M., et al.: J. Biol. Chem., 275, 28888 (1994)

References