L-Tryptophan-7-amido-4-methylcoumarin hydrochloride
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L-Tryptophan-7-amido-4-methylcoumarin hydrochloride

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Category
L-Amino Acids
Catalog number
BAT-007708
CAS number
201860-49-3
Molecular Formula
C21H20ClN3O3
Molecular Weight
397.85
L-Tryptophan-7-amido-4-methylcoumarin hydrochloride
IUPAC Name
(2S)-2-amino-3-(1H-indol-3-yl)-N-(4-methyl-2-oxochromen-7-yl)propanamide;hydrochloride
Synonyms
H-L-Trp-AMC HCl; N-(4-Methyl-2-oxo-2H-1-benzopyran-7-yl)-L-tryptophanamide-hydrogen chloride; (S)-2-amino-3-(1H-indol-3-yl)-N-(4-methyl-2-oxo-2H-chromen-7-yl)propanamide hydrochloride; (2S)-2-amino-3-(1H-indol-3-yl)-N-(4-methyl-2-oxochromen-7-yl)propanamide hydrochloride; H L Trp AMC HCl
Appearance
Pale violet powder
Purity
≥ 99% (HPLC)
Density
1.380±0.06 g/cm3 (Predicted)
Boiling Point
690.1±55.0 °C (Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C21H19N3O3.ClH/c1-12-8-20(25)27-19-10-14(6-7-15(12)19)24-21(26)17(22)9-13-11-23-18-5-3-2-4-16(13)18;/h2-8,10-11,17,23H,9,22H2,1H3,(H,24,26);1H/t17-;/m0./s1
InChI Key
OJTSFONFGYVAIM-LMOVPXPDSA-N
Canonical SMILES
CC1=CC(=O)OC2=C1C=CC(=C2)NC(=O)C(CC3=CNC4=CC=CC=C43)N.Cl
1. Crystallographic characterization of three cathinone hydrochlorides new on the NPS market: 1-(4-methylphenyl)-2-(pyrrolidin-1-yl)hexan-1-one (4-MPHP), 4-methyl-1-phenyl-2-(pyrrolidin-1-yl)pentan-1-one (α-PiHP) and 2-(methylamino)-1-(4-methylphenyl)pentan-1-one (4-MPD)
Marcin Rojkiewicz, Piotr Kuś, Maria Książek, Joachim Kusz Acta Crystallogr C Struct Chem. 2022 Jan 1;78(Pt 1):56-62. doi: 10.1107/S2053229621013401. Epub 2022 Jan 1.
Cathinones belong to a group of compounds of great interest in the new psychoactive substances (NPS) market. Constant changes to the chemical structure made by the producers of these compounds require a quick reaction from analytical laboratories in ascertaining their characteristics. In this article, three cathinone derivatives were characterized by X-ray crystallography. The investigated compounds were confirmed as: 1-[1-(4-methylphenyl)-1-oxohexan-2-yl]pyrrolidin-1-ium chloride (1, C17H26NO+·Cl-, the hydrochloride of 4-MPHP), 1-(4-methyl-1-oxo-1-phenylpentan-2-yl)pyrrolidin-1-ium chloride (2; C16H24NO+·Cl-, the hydrochloride of α-PiHP) and methyl[1-(4-methylphenyl)-1-oxopentan-2-yl]azanium chloride (3; C13H20NO+·Cl-, the hydrochloride of 4-MPD). All the salts crystallize in a monoclinic space group: 1 and 2 in P21/c, and 3 in P21/n. To the best of our knowledge, this study provides the first detailed and comprehensive crystallographic data on salts 1-3.
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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