(3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
Basic information
- CAS
103733-65-9- Standard SMILES
O=C(O)[C@H]1Cc2ccccc2CN1- InChIKey
BWKMGYQJPOAASG-SECBINFHSA-N- Molecular formula
- C10H11NO2
- Average molar mass
- 177.2 g/mol
- Monoisotopic mass
- 177.07897859
Overview
D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid is a member of isoquinolines.
Names & identifiers
- Preferred name
- (3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
- IUPAC
- (3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
- English name
- D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid
- Molecular formula
- C10H11NO2
- Molecular weight
- 177.2
Names & synonyms
(3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acidRefChem:400730620-958-9103733-65-9(R)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acidH-D-TIC-OH(R)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acidD-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acidMFCD001440383-Isoquinolinecarboxylic acid, 1,2,3,4-tetrahydro-, (3R)-D-Tic-OH(3R)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid
Show more names
D-TICAtebant Impurity 4RARECHEM BK PT 0079Icatibant Impurity 4D-PHENYLALANINE ANALOGUED-1,2,3,4-TetrahydroisoquinolineTetrahydroisoquinoline-3-carboxylic acid
30WOC9CAC61,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid, (R)-NCGC00390789-02AS-43020D-1,2,3,4-tetrahydroisoquinoline-3-carboxylic(3R)-1,2,3,4-tetrahydro-3-isoquinolinecarboxlic acid1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid, (+)-SY017614
Database identifiers
Properties
Computed structural properties
- XLogP
- -1.3
- Topological polar surface area
- 49.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 205
Physicochemical properties
- Melting point
- 320 · 320-323 °C (decomp)
- Boiling point
- 372 · 372.0±42.0 °C(Predicted)
- Density
- 1.225 · 1.225±0.06 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- solubility
- Aqueous Acid (Slightly), Aqueous Base (Sparingly, Sonicated)
- form
- Crystalline Powder
- pka
- 2.21 · 2.21±0.20(Predicted)
- color
- White
- InChI
- 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-/m1/s1
- InChIKey
- BWKMGYQJPOAASG-SECBINFHSA-N
- SMILES
- C1C2=C(C=CC=C2)C[C@H](C(O)=O)N1
- CAS DataBase Reference
- 103733 · 103733-65-9(CAS DataBase Reference)
- FDA UNII
- 30 WOC9CAC6 · 30WOC9CAC6
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- wgk
- 3
- hs_code
- 29334900
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P280-P301+P312-P302+P352-P305+P351+P338
Chemistry & industry
Applications
DescriptionD-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid ((3R)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid) is a magnetic, neutral compound. It is used as a pharmacological study to investigate the reaction mechanism and kinetics of the deuteration process. The asymmetric synthesis of D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid has been investigated using vinylene chloride and hydantoin as reactants. There are various parameters that affect the kinetics of this reaction such as solvent type and temperature. The nitric oxide synthase inhibitor activity of D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid has been studied in vitro. Results have shown that it inhibits nitric oxide synthase by binding to the heme iron of the enzyme and preventing the conversion of arginine
Uses(R)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.
Upstream & downstream products
Upstream raw materials
Downstream products
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Related reactions
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Compound notes
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