Piptadenia peregrina

Material Indole-based alkaloid found in seeds, pods, bark, and resins of several South American trees, including Piptadenia peregrina and Virola calophylla, used in the snuffs yopo, epena, and parica. 

Dipterine, the iVb-methyl derivative of tryptamine, occurs in two Asiatic members of the family Chenopodiaceae, Girgensohnia diplera Bge. (71, 72) and Arthrophytum leptocladum Popov (73), and also in the bark of Piptadenia peregrina Benth. (73a). Arthrophytum leptocladum also contains a closely related base, leptocladine (74), identified as Nb-methyltetrahydroharman by synthesis from dipterine and acetaldehyde (73). 

The seeds of Piptadenia peregrina and P. macrocarpa also contain AjA-dimethyltryptamine oxide (75). Since A,A-dimethyltryptamine is readily oxidized on exposure to air, the oxide of this base may be an artifact. 

A report that sheep fed on a perennial grass, Phalaris tuberosa L., developed a condition known as staggers led to the investigation of a related species, P. arundinacea L., and the subsequent isolation from it of 5-methoxy-A-methyltryptamine (XVIII R = H) (116). 5-Methoxy-iV.A-dimethyltryptamine (XVIII R = Me) also occurs naturally, and has been isolated from Dictyoloma incane-scens DC. (40). Both bases have recently been shown to be present in the bark of Piptadenia peregrina Benth. (73a). 

Anadenanthera colubrina, Mucuna pruriens, Piptadenia peregrina,... 

Fabaceae), Arundo donax, Phalaris spp. (Poaceae), Mucuna prwriens, Mimosa hostilis, Piptadenia peregrina (Fabaceae), Virola sp. (Myristicaceae)... 

Cucumis satims (Cucurbitaceae), Mucuna pruriens, Piptadenia peregrina, Prosopisjuliflora (Fabaceae), Hordeum vulgare, fea mays (Poaceae), Lycopersicon esculentum, Nicotiana tabacum, Solanum tuberosum (Solanaceae)... 

An indole alkaloid obtained from the seeds and leaves of Piptadenia peregrina and P. macrocarpa (Mimosaceae). It has also been isolated from species of Amanita (Agaricaceae) and from the skin glands of toads (Bufo spp.). 

An active principle obtained from the seeds and leaves of Piptadenia peregrina (Mimosaceae). 

Piptadenia peregrina (L.) Bentham—165 Piptadenia rigda Bentham—165,168 Piptadenia sp.—165,168 Piptadenia viridijlora (Kunth.) Benth.—168 Piptoporus betulinus (Bull, ex Fr.) Karst.—351 Pithecellobium laetum Bentham—217,270 Pleurotus ostreatus (Jacquin ex Fries) Kummer—342,355-6... 

The corresponding N,A-dimethyltryptamine derivative, bufotenine (4), is hallucinogenic and is found in Anadenan-thera Piptadenia) peregrina (Fabaceae, Mimosoideae) (Schultes and Hofmann, 1973). Both serotonin and bufotenin have 5-hydroxy groups (Fig. 28.5). 

Fig. 28.5. Formation of bufoienin in Anadenanthera (Piptadenia) peregrina and other simple amines (modified from Smith, 1980 u permission of the copyright owner, Springer-Verlag, Berlin).

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