Bufotenin isolation

Drugs that interfere with the metabolism of serotonin have a profound effect on mental state. For example, bufotenin, isolated from Bufo toads from the Amazon jungle, and psilocin, iso-... 

Bufotenine was isolated from skin and parotid gland of the toad Bufo vulgaris in 1893, and from plants and mushrooms. It is also foimd in the toad Bufo marinus that lives in the southern part of the United States and the Caribbean, and in Bufo alvarius, found in the southwestern United States. Amazon explorers had described poisoning by toad and mushroom preparations more than 400 years ago. Street names include black stone, Chan Su, Chinese love stones, cohoba, rock hard. Stud 100, and toad. 

Norbufotenine (5-hydroxy-N-methyltryptamine, N-methylserotonin, 5-OH-NMT) This base is scattered in both the animal and the plant kingdoms. It has been found in quite a few toads and in barley shoots. It has been isolated from the herb Desmodium pulchellum. This is an interesting twilight compound lying halfway between a notorious toxin (bufotenine) and a vital neurotransmitter (serotonin). And it is unexplored, for shame. It has been detected in the urine... 

Bufotenine is also a tryptamine derivative isolated from species of the Anadenantera, a pod-producing plant found in South America and the seeds from the pod can be toasted and ground into a snuff or smoked. 

Bufotenin, a compound isolated from some amphibian toxins... 

Wieland and co-workers (913) in 1931 isolated from the skin secretion of the toad two indole derivatives, bufotenin and bufotenidin, whose correct structure (diagram 24) was established soon after (914) and confirmed by synthesis (416, cf. 363). Dehydrobufotenin was isolated in 1935 (443) and the previously isolated bufothionin (915) shown to be its sulfate ester (916, cf. diagram 24). 

Compared to other psychoactive compounds (e.g., psilocybin, JB-336, and bufotenine), ibogaine (10 mg/kg) had a negligible effect on the aggressiveness of isolated mice and muricidal behavior in rats (126). 

The possibility that an aberrant pathway that utilizes N-methyltransferase might convert the serotonin to 5-hydroxy-N,N-dimethyltryptamine (bufotenine) in schizophrenic patients has fascinated researchers. Bufotenine, which is an alkaloid, was first isolated from the skin glands of toads (of the genus Bufo) as well as of several plant sources. N,N,-Dimethyltryptamine is a reported psychotomimetic and hallucinogen. Since it was found in the CAR test, the possibility that this 5-HT metabolite, if formed in schizophrenics, might be, at least in part, the cause of the disease could not be overlooked. Reports that IV infusion of bufotenine was hallucinogenic in humans, however, have not been corroborated by others, even with high doses. 

Rendon, P. and J. Willy 1985. Isolation of bufotenine from seeds aiPiptadenia mac-rocarpa Benth. Revista Boliviana de Qut-mica 5 39—43. 

Hyla arborea and other hylid frogs are distributed in wide parts of the Old World, the New World and Asia. Low molecular compounds isolated from their skin secretions are serotonin, bufotenin, and histamin. 

Non-isoprenoid Tryptamines.—NAT-Dimethyltryptamine (5), bufotenine (6), and bufotenine N-oxide have been found in the roots and stems of Desmodium caudatum DC. NN-Dimethyltryptamine and bufotenine have also been isolated, together with four other simple tryptamine derivatives (7)—(10), from a red-violet octocoral, Paramuricea chamaeleon, collected in the Bay of Naples. ... 

When Wieland et al. (1934) and Jensen and Chen (1936) isolated bufotenine (iV,N-dimethyl-5-hydroxytryptamine) and related indoleamines from the toad venom gland, they considered them as poisons peculiar to this species of animal. About twenty years elapsed before Rapport et al. (1948) isolated serotonin (5-hydroxytryptamine) from beef blood and determined its structure (Rapport, 1949). With the isolation of serotonin the full significance of the indoleamines in nature began to unfold. 

The occurrence of A (,iVj-dimethyltryptamine in Lespedeza bicolor var. japonica has been substantiated, and other bases have been isolated. These include iVa-methoxy-iVjiVj-dimethyltryptamine (lespedamine) (III), a base not previously encountered from natural sources, bufotenine, and 5-methoxy-Aj.,iVi-dimethyltryptamine (16,17). It is of interest that the crude plant extracts and iVjiVj-dimethyltryptamine are reported to exhibit uterus-contracting properties (27). 

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