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Merck
CN

421626

Sigma-Aldrich

(S)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid

97%

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About This Item

Empirical Formula (Hill Notation):
C10H11NO2
CAS Number:
74163-81-8
Molecular Weight:
177.20
Beilstein:
4842199
MDL number:
MFCD00144533
UNSPSC Code:
12352106
PubChem Substance ID:
24866388
NACRES:
NA.22

Key Documents

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Quality Level

100

Assay

97%

form

solid

optical activity

[α]20/D −168°, c = 1.8 in 1.4 M NaOH

reaction suitability

reaction type: solution phase peptide synthesis

mp

>300 °C (lit.)

application(s)

peptide synthesis

SMILES string

OC(=O)[C@@H]1Cc2ccccc2CN1

InChI

1S/C10H11NO2/c12-10(13)9-5-7-3-1-2-4-8(7)6-11-9/h1-4,9,11H,5-6H2,(H,12,13)/t9-/m0/s1

InChI key

BWKMGYQJPOAASG-VIFPVBQESA-N

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Related Categories

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
09914LD
06727EG
06618MQ
04717LA
10623JR

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Qian-Yu Zhao et al.
Protein and peptide letters, 12(4), 323-326 (2005-05-24)
[Tic(4)]EM1 and [Tic(4)]EM2, new endomorphins (EMs) analogues, caused relaxation of rat aorta rings precontracted with phenylphrine in a concentration-dependent manner and were 240- to 370-fold more potent than EMs. This effect was inhibited by endothelium removal or by incubation with
P A Temussi et al.
Biochemical and biophysical research communications, 198(3), 933-939 (1994-02-15)
The surprising change of selectivity induced by the change of chirality in peptides containing the tetrahydro-3-isoquinoline carboxylic acid (Tic) in second position, interpreted as a conformational preference induced on the Tyr-Xaa-Phe domain, can instead be attributed to the Tyr-Tic message
Yingjie Zhang et al.
Bioorganic & medicinal chemistry, 18(5), 1761-1772 (2010-02-23)
Histone deacetylases (HDACs) are enzymes involved in tumor genesis and development. Herein, we report a novel series of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives as HDACs inhibitors. The preliminary biological screening showed that most of our compounds exhibited potent inhibitory activity against HDACs.
D Pagé et al.
Journal of medicinal chemistry, 44(15), 2387-2390 (2001-07-13)
The design, synthesis and pharmacological evaluation of a novel class of Dmt-Tic dipeptide analogues are described. These resulting analogues bearing different C-terminal functionalities were found to bind to the human delta receptor with high affinity. One specific class of dipeptides
Xiaopan Zhang et al.
Bioorganic & medicinal chemistry, 19(20), 6015-6025 (2011-09-14)
A series of novel 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid derivatives were designed, synthesized and assayed for their activities against aminopeptidase N (APN/CD13) and MMP-2. The results showed that most compounds exhibited higher inhibitory activities against APN than that of MMP-2. Within this series
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