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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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Karolina Pulka
Current opinion in drug discovery & development, 13(6), 669-684 (2010-11-10)
The synthesis of biologically active heterocyclic scaffolds is one of the significant challenges of modern synthetic chemistry. The Pictet-Spengler (PS) reaction, known for approximately a century, remains a particularly popular cyclization method. This review describes recent applications of the PS
Tetrahedron, 48, 9735-9735 (1992)
Fangrui Wu et al.
Journal of the American Chemical Society, 134(3), 1498-1500 (2012-01-11)
The Pictet-Spenglerase strictosidine synthase (STR1) has been recognized as a key enzyme in the biosynthesis of some 2000 indole alkaloids in plants, some with high therapeutic value. In this study, a novel function of STR1 has been detected which allows
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
I M McDonald et al.
Journal of medicinal chemistry, 43(19), 3518-3529 (2000-09-23)
A novel series of nonpeptide CCK(2) receptor antagonists has been prepared, in which 2,7-dioxo-2,3,4,5,6,7-hexahydro-1H-benzo[h][1, 4]diazonine (5) was used as a chemical template. This uncommon ring system was obtained in a highly substituted form and in high yield by ozonolysis of
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