JS-Phenethylamine

The following bases were isolated as their hydrochlorides JV-methyl-4-methoxy-jS-phenethylamine, hordenine, iV-methyltyramine, syne-phrine, and O-methylsynephrine (38). 

A jS-phenethylamine moiety was incorporated into the trans-decalin ring system (45)... 

These compounds are not hydrolyzed by acetylcholinesterase. Possible utility in treatment of Alzheimer s syndrome was suggested. An cK-chloro-jS-phenethylamine (263)irrevers-... 

Figure 12.7. Rotameric forms of dopamine, a flexible jS-phenethylamine.

N-jS-Phenethylamine (309) and N-n-octylamine (310) have been synthesized, respectively , by UAIH4 reduction of N-phenylacetamide and N-octamide prepared by N-ammonolysis in ether (equation 126) in a 25-min total synthesis time. 

Full accounts on the products obtained from the irradiation of the Al-chloro-acetyl-jS-phenethylamine derivatives (1 R = H, Me, or CH2Ph) have appeared (Scheme The structures of (2 R = Me) and of the NiV -diacetate of... 

A facile one-step synthesis " of ( )-cis- and trans-16-hydroxy-15-methoxy-erythrinanone (14 R = OMe, R = OH, X = O) and (15 R = OMe, R = OH, X = O) by the condensation of 2-(ethoxycarbonylmethyl)methylcyclo-hexanone with 3-hydroxy-4-methoxy-jS-phenethylamine in refluxing ethanol without acid catalysis, reported by Kametani and co-workers, has been discussed... 

AT-Methyl-jS-phenethylamine occurs together with dipterine N-methyltryptamine) and leptocladine (3 4-dimethyl-3 4 5 6-tetrahydro-... 

It is not within the scope of this study to offer exhaustive references on the enormous literature accumulated on the pharmacological action and clinical use of ephedrine and ephedrine-like compounds. Additional information may be found in the already cited surveys (p. 340). A symposium on sympathomimetic agents, with contributions by Gold, Hartung, Scholz, Tainter, Beyer and Morrison, Graham, Cartland and Woodruff, has been published in 1945 (287). Bayer s (288) and Mascherpa s (289) papers, Guggenheim s (290) book and the chapter on jS-phenethylamines (pharmacology) of this book may be consulted for more information on sympathomimetic amines. 

Interest in natural and synthetic phenethylamines mounted when Spath in 1919 (3) recognized the jS-phenethylamine skeleton in mescaline, the hallucinatory principle of the peyote. Peyote has been recently discussed in newspapers and current magazines in connection with the campaign against narcotics. An interesting statement has been made by La Barre et al. (174) against the inclusion of peyote in the list of narcotics. It is partially transcribed as follows ... 

It may be assumed that the biosynthesis of jS-phenethylamines in plant tissues follows a similar pattern. The general occurrence of decarboxylases, tyrosinases as well as melanization phenomena gives strong support to this hypothesis, although reliable experimental evidence, such as has been obtained in the case of animal metabolism, is not yet available. 

Halostachine is oxidized to benzoic acid by permanganate. It reacts with thionylchloride giving CeHijNChHCl, m.p. 168-169 (from alcohol) W-methylhalostachine yields with thionylchloride CioHuNCh-HCl, m.p. 202-203 . This compound is reduced by sodium amalgam to the base C10H15N (identical with W-dimethyl-jS-phenethylamine), b.p. 

In Table 1, the families of the species containing simple isoquinolines and isoquinolones are grouped in orders and superorders according to Dahlgren (1975). Species containing only simple isoquinolines are primarily found in the Cactaceae and the Chenopodiaceae of the Caryophyllales and in the Fabaceae (Leguminosae). The species of these three families contain simple isoquinolines as major alkaloids and these often occur together with jS-phenethylamines. 

Gharbo SA, Beal JL, Schlessinger RH, Cava MP, Svoboda GH (1965) A phytochemical study of Doryphora sassafras. I. Isolation of eight crystalline alkaloids from the leaves. Lloydia 28 237-244 Ghosal S, Metha R (1974) jS-Phenethylamine and tetrahydroisoquinoline alkaloids of Desmodium cephalotes. Phytochemistry 13 1628-1629... 

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