(3S)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid (BAT-007766)
* For research use only

(3S)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid is a Quinapril intermediate.

Category
L-Amino Acids
Catalog number
BAT-007766
CAS number
74163-81-8
Molecular Formula
C10H11NO2
Molecular Weight
177.20
(3S)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid
Synonyms
Tic-OH; (S)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid; L-Porretine; L-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid; (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid; H-TIC-OH; (S)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid; 3-Isoquinolinecarboxylic acid, 1,2,3,4-tetrahydro-, (3S)-; Quinapril EP Impurity A; Tic OH
Appearance
White to off-white crystalline powder
Purity
≥ 98% (HPLC)
Density
1.225 g/cm3
Melting Point
> 300 °C
Boiling Point
372.0 °C at 760 mmHg
Storage
Store at 2-8 °C
1.Total syntheses of conformationally constrained didemnin B analogues. replacements of N,O-dimethyltyrosine with L-1,2,3,4-tetrahydroisoquinoline and L-1,2,3,4-tetrahydro-7-methoxyisoquinoline.
Tarver JE Jr1, Pfizenmayer AJ, Joullié MM. J Org Chem. 2001 Nov 16;66(23):7575-87.
The design and synthesis of two conformationally constrained analogues of didemnin B are described. The [N,O-Me(2)Tyr(5)]residue of didemnin B was replaced with L-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic) and L-1,2,3,4-tetrahydro-7-methoxyisoquinoline-3-carboxylic acid (MeO-Tic), which mimic the N,O-dimethylated tyrosine while constraining the conformation of the molecule. Preliminary results indicate that the conformation of the [N,O-Me(2)Tyr(5)]residue closely matches the conformation imposed by the Tic replacement.
2.Relevance of the C-terminal Arg-Phe sequence in gamma(2)-melanocyte-stimulating hormone (gamma(2)-MSH) for inducing cardiovascular effects in conscious rats.
Nijsen MJ1, de Ruiter GJ, Kasbergen CM, Hoogerhout P, de Wildt DJ. Br J Pharmacol. 2000 Dec;131(7):1468-74.
1. The cardiovascular effects by gamma(2)-melanocyte-stimulating hormone (gamma(2)-MSH) are probably not due to any of the well-known melanocortin subtype receptors. We hypothesize that the receptor for Phe-Met-Arg-Phe-amide (FMRFa) or Phe-Leu-Phe-Gln-Pro-Gln-Arg-Phe-amide (neuropeptide FF; NPFFa), other Arg-Phe containing peptides, is the candidate receptor. Therefore, we studied various Arg-Phe containing peptides to compare their haemodynamic profile with that of gamma(2)-MSH(6 - 12), the most potent fragment of gamma(2)-MSH. 2. Mean arterial pressure (MAP) and heart rate (HR) changes were measured in conscious rats after intravenous administration of gamma(2)-MSH related peptides. 3. Phe-Arg-Trp-Asp-Arg-Phe-Gly (gamma(2)-MSH(6 - 12)), FMRFa, NPFFa, Met-enkephalin-Arg-Phe-amide (MERFa), Arg-Phe-amide (RFa), acetyl-Phe-norLeu-Arg-Phe-amide (acFnLRFa) and desamino-Tyr-Phe-norLeu-Arg-Phe-amide (daYFnLRFa) caused a dose-dependent increase in MAP and HR.
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