N-Methyl-DL-tyrosine hydrochloride
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N-Methyl-DL-tyrosine hydrochloride

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An inhibitor of catecholamine synthesis and tyrosine hydroxylase.

Category
DL-Amino Acids
Catalog number
BAT-000442
CAS number
19897-63-3
Molecular Formula
C10H13NO3·HCl
Molecular Weight
231.72
N-Methyl-DL-tyrosine hydrochloride
IUPAC Name
3-(4-hydroxyphenyl)-2-(methylamino)propanoic acid
Synonyms
N-Me-DL-Tyr-OH HCl; (R)-3-(4-Hydroxyphenyl)-2-(methylamino)propanoic acid hydrochloride
Appearance
White powder
Purity
≥ 98% (HPLC)
Melting Point
174-180 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C10H13NO3/c1-11-9(10(13)14)6-7-2-4-8(12)5-3-7/h2-5,9,11-12H,6H2,1H3,(H,13,14)
InChI Key
AXDLCFOOGCNDST-UHFFFAOYSA-N
Canonical SMILES
CNC(CC1=CC=C(C=C1)O)C(=O)O
1. 1-Haloacylpiperazines
S Groszkowski, J Sienkiewicz, L Korzycka Pol J Pharmacol Pharm. 1975 Apr-Jun;27(2):183-6.
By direct acylation of piperazine with halogenocarboxylic acid chlorides in acid medium, the hydrochlorides of 1-haloacylpiperazines were obtained.
2. Metal-free and regiospecific synthesis of 3-arylindoles
Chuangchuang Xu, Wenlai Xie, Jiaxi Xu Org Biomol Chem. 2020 Apr 8;18(14):2661-2671. doi: 10.1039/d0ob00317d.
A convenient, metal-free, and organic acid-base promoted synthetic method to prepare 3-arylindoles from 3-aryloxirane-2-carbonitriles and arylhydrazine hydrochlorides has been developed. In the reaction, the organic acid catalyzes a tandem nucleophilic ring-opening reaction of aryloxiranecarbonitriles and arylhydrazine hydrochlorides and Fischer indolization. The organic base triethylamine plays a crucial role in the final elimination step in the Fischer indole synthesis, affording 3-arylindoles regiospecifically. The reaction features advantages of microwave acceleration, non-metal participation, short reaction time, organic acid-base co-catalysis, and broad substrate scope.
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