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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)

Related Categories

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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Takayoshi Arai et al.
The Journal of organic chemistry, 76(8), 2909-2912 (2011-03-08)
A four-step synthetic route to fully substituted chiral tetrahydro-β-carbolines (THBCs) is described. Starting from the (R,S,S)-Friedel-Crafts/Henry adduct obtained from three-component coupling of an indole, nitroalkene, and aldehyde catalyzed by imidazoline-aminophenol-CuOTf, the (1S,3S,4R)-THBCs were readily synthesized in a three-step operation including
Minoru Tanaka et al.
Bioorganic & medicinal chemistry, 21(5), 1159-1165 (2013-01-23)
Indoleamine 2,3-dioxygenase (IDO) plays a significant role in several disorders such as Alzheimer's disease, age-related cataracts and tumors. A series of novel tryptoline derivatives were synthesized and evaluated for their inhibitory activity against IDO. Substituted tryptoline derivatives (11a, 11c, 11e
Erhad Ascic et al.
Chemical communications (Cambridge, England), 48(27), 3345-3347 (2012-03-01)
An efficient and broadly applicable alternative to the classical Pictet-Spengler synthesis of tetrahydro-β-carbolines is presented. The method relies on metal-catalyzed isomerization of allylic amines to form reactive iminium intermediates which can be trapped by a tethered indole nucleophile.
Kaushik Chanda et al.
Molecular diversity, 15(2), 569-581 (2010-10-12)
The Pictet-Spengler reaction, using polyethylene glycol immobilized tryptophan ester with a variety of ketones, was achieved by refluxing condition in acidic chloroform. The linear as well as cyclic ketones were employed. All the ketones were reacted within 6-8 h to
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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