The Anhalonium Alkaloids

In chemical literature Anhalonium lewinii, A. williamsii Lem. and A. jourdanianum Lewin are mentioned as different species. However, botanists definitely recognize only one species Anhalonium williamsii Britton and Rose Lophophora williamsii (Lemaire) Coulter). It would be worth while to investigate, using fresh and well-identified material, whether only pellotine is present in A. williamsii, as stated by Heffter. Such findings may give support to a revision of the taxonomy of these cacti. 

These small cacti grow from central Mexico to southern Texas and are the material of an illicit commerce, carried out by some Indian tribes. The globular plants are sliced into three or four sections and then dried in the sun these dried pieces are the mescal buttons of the trade. The plant is also known as pellote, peyote, and peyotl it is called challote in Starr County, Texas. Interest in the cactus alkaloids arose when the remarkable use by the Indian tribes and the strange pharmacological properties of this little cactus became known. (See Mescaline, Vol. HI, pp. 331-334, and Cactus Alkaloids, Vol. IV, chap. 27). 

Eleven bases have been isolated from Anhalonium lewinii, three phenethylamines mescaline, V-methylmescaline, and V-acetylmescaline (see /8-Phenethylamines Vol. Ill, chap. 22) and eight simple isoquinolines anhalamine, anhalidine, anhalinine, anhalonidine, pellotine, 0-methyl-d- 

The clarification of the structure and the syntheses of all of the Anhalo-nium alkaloids must be credited to Spath and his coworkers. The accomplishment is all the more remarkable since Spath had to contend with a scarcity of material several fundamental structures were determined on very small samples, left over from Heffter s and Heyl s experiments. 

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Constitution of the Anhalonium Alkaloids. From Heffter s results it was possible to extend the formulas assigned to six of the seven anhalonium alkaloids then known as follows —... 

ALKALOIDS OF THE CACTACEA . Heffter i has recorded the presence of alkaloids in a number of cacti, but only those of Anhalonium spp. have been fully investigated. Heyl obtained an amorphous base, pilocereine, from Pilocereus sargentianus Ore., and Ducloux extracted from Gymnocalycium gibbosum. Haw., basic material which he regarded as a mixture of the anhalonium bases, anhalonine, lophophorine and mezcaline. 

Isoquinoline derivatives occur widely in nature [118]. There are over 600 known isoquinoline alkaloids, one of the largest groups of alkaloids known. With the exception of a few simple systems of the anhalonium type, e.g. anhalamine 77 and anhalonidine 78, constituents of the peyote cactus. 

Comparatively few simple isoquinoline alkaloids have been found to occur naturally. Until now such compounds have been encountered in three or four species of the Cactaceae, in a Chenopodiaceae [Salsola arbuscula Pall. (S. richteri Karel)], in three species belonging to the family of the Fumari-aceae [Corydalis pallida (Thunb.) Pers.,C. awrea Willd., C. tvherosa DC.] and in one Papaveraceae Papaver somniferum L.). While no doubt exists as to the native occurrence of the anhalonium and salsola isoquinolines, hy-drohydrastinine and hydrocotarnine may have been artifacts from the benzylisoquinoline alkaloids of Corydalis tuberosa and Papaver somniferum. 

Lophophora alkaloids. Alkaloids from the Mexican Lophophora cacti ( peyote) cultivated as ornamental cacti in Europe, see cactus alkaloids. The plants contain ca. 5% of alkaloids, mainly phenylethylamine alkaloids and simple isoquinoline derivatives. Their best known property is the generation of colored hallucinations and other sensory changes. The most toxic alkaloid of this group is lophophorine (see Anhalonium alkaloids). 

Peyote (payote, peyotl, from Aztec. nahuatl pey-otl=caterpillar). A small woolly-hairy hedgehog cactus (Lophophora williamsii, Cactaceae) widely distributed in northern central Mexico. The most important constituents responsible for the hallucinogenic activity of P. include Anhalonium or cactus alkaloids such as mescaline and the isoquinoline alkaloids iopho-phorine and pellotine (see Anhalonium alkaloids). Slices of the plant ( mescal buttons ) are eaten or extracts therefrom are drunk to achieve the narcotic state. The Christian Native Church uses P. for ritual purposes. 

The sliced and dried heads of the cactus, Anhalonium lewinii Lopho-phora williamsii) have long been used as an intoxicant by the natives of Mexico and the southwestern part of the United States. Interest in the cactus alkaloids arose when the remarkable use by the Indian tribes and the strange pharmacological properties of this little plant became known. 

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. 

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. 

An alkaloid obtained from the cactus Lophophora williamsii (= Anhalonium williamsii = A. lewinii) (Cactaceae), which grows in the northern regions of Mexico. The cactus is also known by the names peyote or peyotl and dried slices of the cactus are called mescal buttons . 

An investigation of the alkaloids of Anhalonium lewinll and some related compounds was carried out by Kapadia and Rao1 using gas chromatography to study the structure-retention time relationship. A packed 1 % SE-52 column was used and the results are summarized in Table 12.1. 

The powdered material is extracted following the usual procedure. Extractions of the drug and isolation of the alkaloids from Anhalonium lewinii have been described by Heffter (19), Kauder (68), Tomaso (69), and Spath and Becke (1), as well as by Steiner-Bernier (70) and the extraction of alkaloids from Pilocereus sargentianus and Cereus pecien-aboriginum, by Heyl (24, 25). 

Anhalonkim alkaloids. A group of isoquinoline alkaloids from the Mexican cactus species Anhalonium (Lophophora) williamsii (Peyotl) and A. lewinii, with... 

The dried tubers of Aconitum plants (Ranunculaceae) are known as U-zu or Bu-shi in Japan, and are used in Kampo medicine (formerly regarded as a form of traditional Chinese medicine). The crude drug is known to contain very poisonous aconitine-type alkaloids (Section 14.4). On the other hand, the methanol extract of the tubers of Anhalonium carmi-chaeli showed hypertensive activity against rats by intravenous injection. The active component was identified as the phenylethylamine-type alkaloid... 

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