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T13005

Sigma-Aldrich

1,2,3,4-Tetrahydroisoquinoline

95%

Synonym(s):

1,2,3,4-Tetrahydro-2-azanaphthalene, 1,2,3,4-Tetrahydro-2-isoquinoline, 1,2,3,4-Tetrahydroisoquinline, 1,2,3,4-Tetrahydroisoquinoline, 3,4-Dihydro-1H-isoquinoline

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About This Item

Empirical Formula (Hill Notation):
C9H11N
CAS Number:
91-21-4
Molecular Weight:
133.19
Beilstein/REAXYS Number:
116156
EC Number:
202-050-0
MDL number:
MFCD00006896
UNSPSC Code:
12352100
PubChem Substance ID:
24899955
NACRES:
NA.22

Quality Level

100

assay

95%

refractive index

n20/D 1.568 (lit.)

bp

232-233 °C (lit.)

mp

−30 °C (lit.)

density

1.064 g/mL at 25 °C (lit.)

SMILES string

C1Cc2ccccc2CN1

InChI

1S/C9H11N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-4,10H,5-7H2

InChI key

UWYZHKAOTLEWKK-UHFFFAOYSA-N

Gene Information

human ... PNMT(5409)
rat ... Adra2a(25083) , Htr1a(24473)

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Related Categories

signalword

Danger

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 3 Oral - Acute Tox. 4 Inhalation - Aquatic Chronic 3 - Eye Dam. 1 - Skin Corr. 1B - STOT SE 2

Storage Class

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

210.2 °F - closed cup

flash_point_c

99 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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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Sigma-Aldrich

CDS002535

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Sigma-Aldrich

515574

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Dengfeng Dou et al.
Journal of combinatorial chemistry, 12(6), 836-843 (2010-10-05)
The 1-oxo-1, 2, 3, 4-tetrahydroisoquinoline and 1-Oxo-1, 2-dihydroisoquinoline scaffolds were utilized in the design and solution phase synthesis of focused libraries of compounds for screening against West Nile Virus (WNV) protease. Exploratory studies have led to the identification of a
John Porter et al.
Bioorganic & medicinal chemistry letters, 19(6), 1767-1772 (2009-02-17)
The separation of atropisomeric conformers of 1,2,3,4-tetrahydroisoquinoline amide Bcl-2 ligands allowed the identification of the bioactive conformer which was subsequently confirmed by X-ray crystallography.
Sean R Klopfenstein et al.
Bioorganic & medicinal chemistry letters, 16(6), 1574-1578 (2006-01-03)
High-throughput screening of the P&GP corporate repository against several protein tyrosine phosphatases identified the sulfamic acid moiety as potential phosphotyrosine mimetic. Incorporation of the sulfamic acid onto a 1,2,3,4-tetrahydroisoquinoline scaffold provided a promising starting point for PTP1B inhibitor design.
Gerardo Della Sala et al.
Marine drugs, 16(12) (2018-11-30)
The ubiquitin-proteasome pathway (UPP) is the central protein degradation system in eukaryotic cells, playing a key role in homeostasis maintenance, through proteolysis of regulatory and misfolded (potentially harmful) proteins. As cancer cells produce proteins inducing cell proliferation and inhibiting cell
Lucie Cahlíková et al.
Natural product communications, 5(7), 1035-1038 (2010-08-26)
The roots and aerial parts of Eschscholzia californica Cham. (Papaveraceae) were extracted with ethanol. Repeated column chromatography, preparative TLC, and crystallization led to the isolation of fourteen isoquinoline alkaloids, the structures of which were determined on the basis of spectroscopic
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