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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:
116156
EC Number:
202-050-0
MDL number:
MFCD00006896
UNSPSC Code:
12352100
PubChem Substance ID:
24899955
NACRES:
NA.22

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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Signal Word

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 Code

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

WGK

WGK 3

Flash Point(F)

210.2 °F - closed cup

Flash Point(C)

99 °C - closed cup

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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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
Staffan Skogvall et al.
Pulmonary pharmacology & therapeutics, 21(1), 125-133 (2007-03-22)
Current drugs including beta-agonists have limited smooth muscle relaxant effects on human small airways. Yet this is a major site of obstruction in asthma and chronic obstructive pulmonary disease (COPD). This study explores human small airway relaxant effects of RESPIR
Matthias Ludwig et al.
European journal of medicinal chemistry, 41(8), 1003-1010 (2006-05-06)
A series of 1-aryl-1,2,3,4-tetrahydroisoquinoline and 8-methyl-1-aryl-1,2,3,4-tetrahydroisoquinoline derivatives was evaluated for affinity to the PCP binding site of the NMDA receptor complex. The (S)-configured tetrahydroisoquinoline derivative (S)-4 e x HCl bearing a 2-methylphenyl substituent in position 1 of the heterocyclic ring
Gary L Grunewald et al.
Journal of medicinal chemistry, 49(18), 5424-5433 (2006-09-01)
3-Fluoromethyl-7-(N-substituted aminosulfonyl)-1,2,3,4-tetrahydroisoquinolines (14, 16, and 18-22) are highly potent and selective inhibitors of phenylethanolamine N-methyltransferase (PNMT). Molecular modeling studies with 3-fluoromethyl-7-(N-alkyl aminosulfonyl)-1,2,3,4-tetrahydroisoquinolines, such as 16, suggested that the sulfonamide -NH- could form a hydrogen bond with the side chain of
Ajay Kumar Srivastava et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 17(17), 4905-4913 (2011-03-16)
We herein report a robust and efficient synthetic route to highly functionalized enantiopure 1,2,3,4-tetrahydroisoquinolines (THIQs) from Garner aldehyde. We utilized the inherent chirality of Garner aldehyde through 1,2- and 1,3-/1,4-asymmetric inductions iteratively to obtain 1,2,3,4-tetrasubstitued THIQs using rigid and isolable
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