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300764

Sigma-Aldrich

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

98%

Synonym(s):

Noreleagnine, THBC, Tetrahydronorharman, Tryptoline

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About This Item

Empirical Formula (Hill Notation):
C11H12N2
CAS Number:
16502-01-5
Molecular Weight:
172.23
MDL number:
MFCD00004954
UNSPSC Code:
12352100
PubChem Substance ID:
24857939
NACRES:
NA.22

Assay

98%

form

liquid

mp

206-208 °C (lit.)

SMILES string

C1Cc2c(CN1)[nH]c3ccccc23

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

InChI key

CFTOTSJVQRFXOF-UHFFFAOYSA-N

Gene Information

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

General description

Ozonolysis of the enamine bond of 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole derivatives was studied.

Application

1,2,3,4-Tetrahydro-9H-pyrido[3,4-b]indole was employed in alkaloid synthesis and in studies on neurodegenerative diseases.
  • Reactant for synthesis of the indolyl-β-carboline alkaloid eudistomin U via IBX mediated room temperature oxidative aromatization
  • Reactant for preparation of neuroprotective HDAC6 inhibitors
  • Reactant for preparation of aminofuranopyrimidines as EGFR and Aurora A kinase inhibitors
  • Reactant for preparation of inhibitors of CDK4
  • Reactant for preparation of tetrahydrocarboline derivatives of as human 5-HT5A receptor ligands
  • Reactant for preparation of 5-(diaminomethyl)-2,4-aminopyrimidines as dihydrofolate reductase inhibitors and antibacterial agents

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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J. Chin. Chem. Soc., 41, 231-231 (1994)
Christian O Alberto et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 31(29), 10671-10676 (2011-07-22)
Melanin-concentrating hormone (MCH) is a hypothalamic neuropeptide that promotes positive energy balance and anxiety. Since dopamine (DA) is also closely implicated in these functions, the present study investigated the effect of DA on MCH neurons. Using whole-cell patch-clamp recordings in
Jutamas Jiaranaikulwanitch et al.
Bioorganic & medicinal chemistry letters, 20(22), 6572-6576 (2010-10-15)
Tryptoline, a core structure of ochrolifuanine E, which is a hit compound from virtual screening of the Thai herbal database against BACE1 was used as a scaffold for the design of BACE1 inhibitors. The tryptoline was linked with different side
Nermin S Ahmed et al.
Archiv der Pharmazie, 344(3), 149-157 (2011-03-09)
Starting from tadalafil as a template, a series of functionalized tetrahydro-β-carboline derivatives have been prepared and identified as novel potent and selective PDE5 inhibitors. Replacing the 3,4-methylenedioxyphenyl at position 6 of tadalafil, together with elongation of the N2-methyl substituent and
Fang-Yuan Chang et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(7), 2478-2483 (2013-01-11)
Natural product discovery by random screening of broth extracts derived from cultured bacteria often suffers from high rates of redundant isolation, making it ever more challenging to identify novel biologically interesting natural products. Here we show that homology-based screening of
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