Substituted phenylethylamine

OH-indoles from substituted phenylethylamines TL 723(1970) 4-Alkylindoles from 4-Br or iodoindoles BER 104,2027(1971) Indoles from cyclohexanones and allylamines C.R. Acad. Sci. Paris 272,1509(1971)... 

Table III. Comparative Activity of Substituted Phenylethylamines in Three Octopamine-sensitive Systems from Arthropods.

From the chemical point of view, adrenergic drugs have a lot in common, and are examined as substituted phenylethylamines. 

Rx (Ophthalmic) with tropicamide (Diophenyht) with pyrilamine (Prefrin-A) Cfiemical Class Substituted phenylethylamine... 

This is a tetrameric copper-containing glycoprotein, which catalyzes the conversion of dopamine into norepinephrine, a hormone/neurotransmitter, and also the hydroxylation of a number of substituted phenylethylamines.1401 1403 Consideration of this enzyme has been hindered by uncertainty over the stoichiometry of binding of copper, and, until recently, there seemed to be good evidence for four copper ions per molecule.1 4 However, there is now convincing support for a stoichiometry of eight copper ions per molecule, with two per subunit.1405,1406 This conclusion is based upon analysis and titration methods. 

In a similar manner, the 2-cyano-6-oxazolopiperidine synthon is useful for the chiral synthesis of in-dolizidine (monomerine piperidine [(+)- and (-)-coniine and dihydropinidine] and quinolizidine alkaloids.2-Hydroxymethyl-1-amino-1-cyclopropanecarboxylic acid (-)-(2I )-hydroxy-(3S)-nonylamine and a-substituted phenylethylamines are obtained in optically active form from (-)-N-cyanomethyl-4-phenyloxazolidine. 

This reaction applied to a mixture of a benzyl cyanide and various amines affords a convenient route to N-substitute phenylethylamines [equation (b)]. Pharmacologically active amines are obtained in excellent yield, as in the synthesis of epinin dimethyl ether [equation (c)] ... 

Further reactions may occur after the formation of a Schiff base. Thus aldehydes react with substituted phenylethylamines under mild experimental conditions to form ultimately tetrahydroisoquinolines i . A particular case of this is the reaction between pyridoxal and DOPA [Figure 4.5). A similar reaction occurs between pyridoxal and histidine [Figure 4.5). The observation that DOPA decarboxylase is subject to substrate inhibition aroused... 

Studies of this type indicate that substituted phenylethylamines are effective inactivators of pyridoxal phosphate if they have a phenolic group in the position meta to the side chain . The presence of a methyl substituent in the alpha position relative to the amino group markedly slows the rate of inactivation of the co-enzyme >. ... 

Other methyl-substituted phenylethylamines (phenylisopropylamines). such as (S)-(+)-amphetamine and (S)-(+)-methamphetamine, which lack both ring substituents I side-chain hydroxyl, are sufficiently lipophilic to cross the blood-brain barrier readily and cause dramatic CNS stimulation, which gives them serious abuse... 

Tuckerman MM, Mayer JR and Nachod FC, Anomalous pKa values of some substituted phenylethylamines, ]ACS, 81, 92-94 (1959). 

Isoquinoline alkaloids are found primarily in the Cactaceae, Chenopodiaceae, and Fabaceae (Guinaudeau and Bruneton, 1993 Mata and McLaughlin, 1982). The Cactaceae also elaborate 3-phenylethylamines see chapter 28) that cooccur with tetrahydroisoquinoline alkaloids. The latter appear to have evolved by cyclization of variously substituted phenylethylamines with suitable ring-closing units. A comprehensive listing of isoquinoline alkaloids in cacti has been published (Lundstrom, 1983). 

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