Cactus alkaloids

Pinidine and Coniine Nicotiana Alkaloids yV-Methylpelletierine Lycopodium Alkaloids Lyduraceae Alkaloids Pyrrolizidine Group Tropane and Pyrrolidine Alkaloids Quinoline and Acridme Alkaloids Benzodiazepine Alkaloids Tylophora Alkaloids Cactus Alkaloids Ephedrine... 

Classification based on botanical origin of the alkaloids are also used, e.g., Papaver (opium) alkaloids. Cinchona alkaloids, Rauvolfia alkaloids, Catharan-thus alkaloids, Strychnos alkaloids. Ergot alkaloids, cactus alkaloids, and Solanum alkaloids. The structures of some alkaloids are shown in Figure 1. 

There is a relatively large number of alkaloids which maybe considered as simple phenethyl amine [64-04-0] (59, R = H), CgH N, or tyramine [51-67-2] (59, R = OH), CgH NO, derivatives. These iaclude mescaline (61) from the small wooly peyotyl cactus l ophophora mlliamsii (L emaire) Coult. anhalamine (62) and lophocerine (63) from other Cactaceae, and the important antamebic alkaloids (—)-protoemetiae (64), (—)-ipecoside (65), and (—)-emetine (66) from the South American straggling bush Cephaelis ipecacuanha (Brotero) Rich. AH of these bases appear to be derived from tyrosiae (25,... 

The early stmctural evideace, physical properties, and aromaticity of isoquiaoline have been discussed at the beginning of this article. Two additional trivial names are encountered occasionally 2-benzaziae and leucoline. The widespread occurrence of this stmcture ia such important alkaloids as those found ia cactus, opium, and curare has created a long-standing iaterest ia its syathesis and properties (4). 

The following alkaloids are included in this section as simple woquinoline bases only one of them, carnegine, has been obtained from a cactus species (Cereus). 

Alkaloids of Salsola Richtsri. This member of the botanical family Chenopodiaceie has been shown by Orekhov and Proskurnina to contain three alkaloids of which two are closely related to the typical cactus alkaloids. 

Mescaline and related alkaloids are found in varying amounts in cacti of the genera Lophophora, Gymnacalycium, Stensonia, Mammillaria, Ariocarpus, Opuntia, Trichocereus, Pelecyphora, and probably others. Members of the Native American Church do quite well with the dried cactus, but extraction of mescaline is desirable since the pure compound seems to produce fewer unpleasant side effects (e.g., nausea). For an excellent review on the occurrence and chemistry of the mescaline type compounds, see JPS 59,1699(1970) (cf. JPS 60,655(1971)). Various species of these cacti occur in southwestern U.S. as well as Central and South America and have been used by the Aztecs and others for millennia. For a good review of peyote see Lloydia 36,1-58(1973). 

More than 55 alkaloids have been isolated from peyote. Mescaline (3,4,5-trimethoxy-j8-phenethylamine) is the primary psychoactive alkaloid of the peyote cactus, and by far the one that has been most studied (figure 9.6). These may be categorized into phenethylamines (including mescaline), isoquinolones, and Krebs acid conjugates. See table 9.2 for a partial list of peyote alkaloids. 

Cawe (Pachycereus pecten-aboriginum) is yet another species of hallucinogenic cactus, which grows in Mexico. It is also a columnar cactus, growing up to 35 feet in height. It is known as Cawe or Wichowaka to the Tarahumara. Studies have identfied 4-hydroxy-3-methoxyphenylethylamine and 4-tetrahydroisoquinoline alkaloids as the probable psychoactive constituents. 

Pardanani JH, McLaughlin JL, Kondrat RW, Cooks RG. (1977). Cactus alkaloids XXXVI. Mescaline and related compounds from Trichocereus peruvianus. Lloydia. 40(6) 585-90. 

Mescaline is an alkaloid isolated from the peyote cactus, species Lophophora williamsii or Anhalonium lewinii, that grows in the southwestern United States and in Mexico. Mescaline is found in buttons that grow on top of the plant. Aztec and Native American Indians used the buttons in religious rites and for treatment of snakebite, flu, and arthritis. Some street names include bad seed, blue caps, cactus buttons, devils root, mesc, moon, peyote, shaman, and tops. 

Mescaline [54-04-6] (2-(3,4,5-trimethoxyphenyl)ethylamine) is the active ingredient in mescal buttons (peyotl or peyote), which are the dried tops of the Mexican dumpling cactus l ophopora wilhamsi. Mescaline produces visual hallucinations on ingestion. Its possible use as a psychotomimetic drug in the field of mental health has been studied (see Alkaloids Psychopharmacologicalagents). 

The widespread occurrence of the isoquinoline (2) structure in such important alkaloids as those found in cactus, opium, and curare has created a long-standing interest in its synthesis and properties. 

One part is the large collection of psychoactive compounds known as the phenethylamines. The first known plant psychedelic was mescaline, or 3,4,5-trimethoxyphenethylamine. This simple one-ring alkaloid was discovered in the North American dumpling cactus Peyote (Anhalonium williamsii) in the late nineteenth century, and is now known to be a component of over fifty other cacti. Over a dozen other cactus phenethylamines have been isolated and identified, and there are perhaps a hundred synthetic analogues that are now also known to be psychedelic in action. This body of information has been published by my wife Ann and me as a book entitled "PIHKAL A Chemical Love Story." PIHKAL stands for Phenethylamines I Have Known and Loved. 

Our explorations with peyote went on, and we were more and more impressed with the importance of the effects of this substance when taken by people with a motivation toward better understanding of themselves and of life, and when given by one with similar motivation and an awareness of the hazards of improper use. Later we experimented with the use of mescaline, the psychedelic alkaloid present in the peyote cactus, and found the effects to be identical with those we had obtained through the use of peyote itself. 

The most abundant alkaloid in Coryphantha macromeris, normacromerine, has been shown to originate from tyrosine (330). Tyramine and JV-methyltyramine are efficiently incorporated into normacromerine while octopamine and dopamine are poor precursors. Norepinephrine, epinephrine, normetanephrine, and meta-nephrine have all been shown to be biosynthetically incorporated into normacromerine, and they have also been shown to be naturally occurring trace intermediates in this cactus species (331, 334). Normacromerine is only slowly converted to macromerine in C. macromeris (332). The results indicate that alternative pathways to normacromerine exist precise conclusions regarding the biosynthesis of normacromerine must await further studies. 

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