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Merck
CN

300764

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
NACRES:
NA.22
PubChem Substance ID:
24857939
UNSPSC Code:
12352100
MDL number:
MFCD00004954
Assay:
98%
Form:
liquid

Key Documents

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Product Name

1,2,3,4-Tetrahydro-9H-pyrido[3,4-b]indole, 98%

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

SMILES string

C1Cc2c(CN1)[nH]c3ccccc23

InChI key

CFTOTSJVQRFXOF-UHFFFAOYSA-N

assay

98%

form

liquid

mp

206-208 °C (lit.)

Quality Level

100

Gene Information

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

Related Categories

Application

1,2,3,4-Tetrahydro-9H-pyrido[3,4-b]indole was employed in alkaloid synthesis and in studies on neurodegenerative diseases.
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  • Reactant for preparation of neuroprotective HDAC6 inhibitors
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  • 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

General description

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000242253
0000242251
0000233234
0000242253
0000242251

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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
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
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
Tetrahedron, 48, 9735-9735 (1992)
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
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