Lophophora williamsii mescaline from

Mescaline A catecholamine hallucinogen, obtained from the peyote cactus (Lophophora williamsii). 

The natural prototype for the phenylalkylamines is mescaline (Structure 1), isolated from the peyote cactus (Lophophora williamsii) by Heffter in 1896 (100) and subsequently obtained synthetically by Spath in 1919 (218). Used for many centuries in the form of peyote by Indians in Mexico and the American Southwest (3), it is often referred to as one of the classic hallucinogens, along with psilocybin, psilocin, and LSD. Little structure-activity work was directed toward mescaline or its congeners until 1955, when Peretz et al. (174) reported that a-methyl mescaline (TMA) (8), which represented a hybrid of the structure... 

Figure 5. An example of protoalkaloids. Mescaline is the alkaloid derived from L-tyrosine and extracted from the Peyote cactns (Lophophora williamsii) belonging to the Cactns family (Cactaceae). MescaUne has strong psychoactive and haUncinogenic properties. Peyote cactns grows in the desert areas of northern Mexico and the sonthern parts of the USA. This plant was nsed in Pre-Colnmhian America in the shamanic practice of local tribes.

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 (peyote) is one such drug that has a cultural history dating from before the time of Christ as well as a separate history as a street drug. It is derived mainly from two members of the Cactaceae family—the peyote cactus (Lophophora williamsii) and the San Pedro cactus (Trichocereus pachanoi). 

Mescaline (3,4,5-trimethoxyphenethylamine) (Fig. 5) is mainly contained in Lophophora williamsii peyote, a cactus native to the deserts of Mexico. Peyote contains an average of about 1.5 % of mescaline. It is often synthetic and looks like a clear powder with colors ranging from white to brown, depending on purity. 

Throughout the 1950s and 1960s, mescaline could be purchased from several chemical supply houses in the form of sulfate or hydrochloride crystals. In 1970, mescaline and peyote were "scheduled as part of a Comprehensive Drug Abuse Prevention and Control Act, which established penalties for possession, manufacture or distribution "a term of imprisonment of not more than 15 years, a fine of not more than 25,000, or both. Title 21 proscribes possession of "all parts of the plant presently classified as Lophophora williamsii, whether growing or not, the seeds thereof, any extract from any part of such a plant, every compound, salt, derivative, mixture or preparation of such a plant, its seeds or extracts. ... 

The sixty or so alkaloids in Lophophora williamsii fall mainly into two groups the 0 -phenethylammes, to which mescaline belongs, and a larger assortment of tetrahydroisoquinolines. Both kinds differ from LSD and most other compounds regarded as psychedelics in that they don t have a full indole structure. 

Aromatic amino acids that originate from the shikimate pathway also act as precursors to many alkaloids. Alkaloids that contain a phenylethylamine moiety are derived from L-tyrosine or its oxidation product L-dihydroxyphenylalanine (L-DOPA). Mescaline (N7) originating from the latter amino acid is known to occur in several cacti and is responsible for the hallucinogenic activity of peyote (Lophophora williamsii, Cactaceae). Lophocerine is a tetrahydroisoquinoline alkaloid derived from L-dopamine and found to occur in a different Lophophora species, L. schotti. 

Cactus Alkaloids.—Detailed attention has been given to establishing the sequence of hydroxylation and methylation which leads from dopamine (53) to mescaline (57). The combined results from Lophophora williamsii and Trichocereus pachanoi establish that methylation of dopamine to (54) is a first step neither... 

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. 

In contrast, mescaline [104] is an exogenous arylethylamine from the Mexican cactus species Peyote (Aztec "root that excites" Lophophora williamsii), which causes visual hallucinations, and which had already been used by the indigenous inhabitants of Mexico in the pre-Columbian era as a narcotic for their ritual festivals (Fig. 6.34). In 1896, mescaline was isolated for the first time from Lophophora williamsii by Arthur Heffter (1859-1925). In 1919, Ernst Spath (1886-1846) recognised its structural relationship to the catecholamines. 

The order of methoxylation and oxidation steps varies. In some instances, the 3,4-dihydroxyphenylethylamine (dopamine) precursor may be modified before condensation occurs. Despite their structural similarity, pellotine (2) and anhalamine (1) are probably synthesized along distinct pathways from mescaline (4). All three alkaloids co-occur in Lophophora williamsii. 

In addition to marijuana (described in the last chapter), another form of plant-based drug exhibit seen in crime labs contains mescaline. This hallucinogen is obtained from the peyote (peyotl) cactus (Lophophora williamsii). Psilocyn (psilocin is also an accepted spelling) and psilocybin (psilocybine), are obtained from the mushroom Psilocybe mexicam, and are members of the indole... 

---