Pachycereus

The pharmacological action of bases from Cereus coryne Solm, Pachycereus marginatus, Trichocereus terscheki, Britton and Rose, and T. candicans B. and R., has also been recorded. T. terscheki is stated to contain trichocereine (A-dimethylmezcaline) and 3 4-dihydroxyphenyl-ethyltrimethylammonium hydroxide. The latter is probably also present in Cereus coryne. T. candicans is stated to contain hordenine (anhaline) and p-hydroxyphenylethyltrimethylammonium hydroxide (candicine). 

Pachycarpine (d-sparteine), 118 Pachycereus marginatits, 161 Paipunine, 767 Palicourea rigida, 781 Palmatine, 328, 329, 342, 345 Palmatine and associated alkaloids, constitution, 342 Palmatine-acetone, 288 Palmatisine, 674 Palustrine, 773... 

Cawe Pachycereus pecten-aboriginum Cactus 4-hydroxy-3-ethoxy- phenylethylamine... 

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. 

Consider chemistry. What are isoquinolines These are chemical structures built around a two-ring compound. This compound, Isoquinoline, consists of a benzene ring and pyridine ring fused together at a specific bond. There is a pattern of substitution that gives an isoquinoline its absolute definition. Thus, for example, Salsoline is an isoquinoline, which is a major component of the Pachycereus pecten-aboriginum plant. 

Pachycereus pecten-aboriginum (Cactaceae) aps 15,127 78 Salsola arbuscula (Chenopodiaceae) ber 67,878 34 Salsola kali (Chenopodiaceae) book 6 Salsola pestifera (Chenopodiaceae) iant 2, 86 85 Salsola richteri (Chenopodiaceae) rr 16, 86 80... 

Hammada articulata (Chenopodiaceae) apf 48,219 90 Pachycereus pecten-aboriginum (Cactaceae) aps 15,127 78... 

After the discovery of mescaline in the San Pedro cactus, it was soon found in other tall, columnar Trichoceri as well as in a Stetsonia species from South America, in Cereus jamacaru from Brazil, and in the giant Pachycereus pecten-aboriginum of Mexico. (The Mexican cactus contains another psychoactive compound—pectenine—which also appears in the Camegiea gigantea of the U.S. Southwest, where it is called "carnegine. ... 

Heliamine, iV-methylheliamine, pellotine, and tehuanine have been isolated from the cactus Pachycereus weberi together with the novel alkaloids nortehuanine (4 R1 = R2 = OMe, R3 = H), lemaireocereine (4 R1 = R2 = H, R3 = OMe), weberine (4 R1 = R2 = R3 = OMe), and weberidine (4 R1 = R2 = R3 = H), the structures of which, with the exception of weberine, were confirmed by synthesis.12 Noroxy-hydrastinine and 6,7-dimethoxy-2-methylisoquinolone have been isolated from... 

The aromatic, tetramethoxy-substituted, tetrahydroisoquinoline alkaloid weberine has been isolated recently from extracts of the Mexican cactus Pachycereus weberi (38). The rare occurrence of four adjacent methoxy groups on an aryl moiety prompted the synthesis and examination by crystal-structure analyses of analogs and derivatives with four and five adjacent methoxy groups on the phenyl ring. In contrast to the problem with... 

Euphorbia fischeriana Fagara rubescens Pachycereus pectenaboriginum... 

Pachycereus pectenaboriginum Salsolidine C.Tani, N. Nagakura, andN. Sugiyama, Yakugaku Zasshi, 1975,9S,838 Chem.Abs., 1975,83,93 897)... 

In agreement with the results obtained in Lophocereus schottii on the origin of the C5 unit (C-1,T,2, 3, 4 ) in lophocerine (62), a specific incorporation of [3, 4- C]mevalonic acid and [2- " C]leucine was obtained into this alkaloid in Pachycereus marginatus. Degradation revealed a labelling pattern consistent with an equal distribution between C-T and C-4 plus C-3 from the experiment... 

Pachycereus pecten-abori num (i, Note 7) Ifbung branches of this gigantic cactus... 

Cereus pecten-aboriginum Engelmann, syn. Pachycereus pecien-aborigi-num (Engelmann) Britton and Rose, contains pectenine (identical with carnegine) (24). 

It is interesting that the tertiary and quaternary tyramine derivatives found in the cacti, such as hordenine and candicine, although they take up appreciable amounts of oxygen, do not form pigments when oxidized by tyrosinase [Duli re and Raper (11)]. However, tyrosine or some other derivative must be present in all cacti since the darkening of cut stems, preceded by a red phase, is characteristic for the whole family. Roca (13) found tyrosine, tyrosinase, and unidentified alkaloidal substances in the Mexican cactus, Pachycereus marginatus Britton and Rose. Tyrosinase has been observed also in Trichocereus candicans Britton and Rose, which contains the alkaloids candicine and hordenine. 

The Mexican cactus Pachycereus pecten-aboriginum has been shown to contain salsoline (6 R = H, = Me) and the new bases isosalsoline (6 R = Me, R = H), the isomeric arizonine (7) (which has the same orientation of oxygen substituents as is found in tepenine), and heliamine, which is 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline. Salsoline (6 R = H,R = Me) and salsolidine (6 R = R = Me), on treatment with ethylene oxide, afford the/3>hydroxyethyi compounds (8 R = H, R = OH) and (8 R = Me, R = OH), and these have been converted into a series of esters by reaction with acid chlorides. The jS-chloroethyl compound (8 R = H, R = Cl) has been shown to decrease... 

In addition to simple monomeric units with isoquinoline structures, a number of dimeric and oligomeric alkaloids of this series are known. An example of this type, pilocereine (8) (Fig. 32.3), known from Pachycereus, Pilocereus, and Lophocereus (all Cactaceae), is derived by coupling of isoquinoline alkaloid units (probably by a free-radical mechanism, although proof for this is lacking), much in the same manner as the dimerization process leading to bisbenzyliso-quinoline alkaloids, a topic discussed below. 

Alkaloid from Pachycereus weberi (Cactaceae). Bpo 1 115° (synth.). ... 

Pachycereus tehuantepecanus Mac Dough H. Bravo Tepenine, tehaunine... 

Pachycereus weberi (Coult.) Backeb. Anhalonidine, heliamine, lemaireocereine, N-methylheliamine, northehaunine, peUotine, tehaunine, weberidine, weberine... 

The tallest Mexican columnar cactus Pachycereus weberi contains a great variety of differently substituted tetrahydroisoquinoHnes, mono-, di-, tri- and tetraoxyge-nated in the aromatic nucleus. Apparently this cactus has a highly evolved enzyme system for ring oxidation and 0-methylation (Mata and McLaughlin 1982). 

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