Phenylethylamine alkaloids are natural products with an open tetrahydroisoquinoline structure (see substituted phenethylamines.
Occurrence Phenylethylamine alkaloids occur in many plants, including members of the families Cactaceae and Leguminosae, as well as Ranunculaceae, Celastraceae, Taxaceae, Malvaceae, Papaveraceae, Poaceae, and Amaryllidaceae.
Representatives The eponym of this alkaloid group is the alkaloid phenethylamine. (-)-ephedrine is found in Ephedra vulgaris, Ephedra sinica, and other Ephedraceae species. One of the best-known representatives is mescaline from the cactus Lophophora williamsii.
Properties Phenylethylamine alkaloids are physiologically active compounds and are therefore of considerable importance. Epinephrine (adrenaline) is known as an adrenal hormone. The β-oxidized macromerine is reported to possess hallucinogenic properties. Pseudoephedrine and norephedrine are sympathomimetic substances with effects similar to those of ephedrine. Mescaline is one of the longest-known hallucinogenic substances. (-)-Ephedrine is used as a bronchodilator for asthma attacks. It also increases blood pressure and stimulates the sympathetic nervous system. The mescaline-containing “peyote buttons” (the dried out bodies of the cactus Lophophora williamsii) are chewed to produce classical psychedelic effects.
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