Mescaline alkaloid

However, even the best-written book must fail to transmit an experience that many claim is incommunicable, and the doctor often wishes that he could enter the illness and see with a madman s eyes, hear with his ears, and feel with his skin. This might seem an unlikely privilege, but it is available to anyone who is prepared to take a small quantity of the alkaloid mescaline or a minute amount of the ergotlike... 

Of the alkaloids so far identified in just L. william-sii alone, 15 are Beta-phenethylamine and simple isoquinoline alkaloids. Mescaline, N-methylmescaline, N-acetylemescaline, anhalamine, anhalonine, anhalidine, anhalinine, anhalonidine, lophophorine, O-methylan-halondedine, and pellotine have all been identified as the principal components of the plant. However, only mescaline has so far been determined to cause hallucinations. 

Effects Competitive acetylcholine inhibitor at receptor site (postganglionic junction). Does not prevent acetylcholine liberation. Hallucinogen, similar to scopolamine, but producing more excitement and less stupor. Potentiates other psychotropics, including opium, cannabis, harmala alkaloids, mescaline. 

The replacement of that one methyl group with an ethyl group leads to a nice jeu de mots. The play on words depends on a remarkable coincidence. The name of the alkaloid mescaline stems from an ancient Nahuatl word for a drink (Mexcalli) which also provided the source of the term Mescal (an Agave of entirely different pharmacology). The prefix for the simplest, the one carbon organic radical, is methyl. 

The simple alkaloid mescaline is the main active component of L. ml-liamsii of (10) and o Trichocereus pachanoi of (12), and the yield of mescaline is said to be 2% of the dried material. Mescaline is a phenethylamine (=phenylethylamine) type alkaloid, like ephedrine. 

The widespread utility of the Nenitzescu indole synthesis from o,p-dinitrostyrenes is illustrated by the examples in Table 1. Entry 1 features the synthesis of 5,6,7-trimeth-oxyindole, a possible intermediary metabolite of the alkaloid mescaline [7], Of the seven routes pursued by Benington and colleagues, only the Nenitzescu method proved practical. The conventional iron/acetic acid method... 

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,... 

Both of the alkaloids anhalamine (62) from l ophophora williamsii and lophocerine (63) from l ophocereus schotti were isolated (after the properties of purified mescaline had been noted) in the search for materials of similar behavior. Interestingly, lophocerine, isolated as its methyl ether, after dia2omethane treatment of the alkaU-soluble fraction of total plant extract, is racemic. It is not known if the alkaloid in the plant is also racemic or if the isolation procedure causes racemization. 

The answer is b. (Kn.lzu.ng, p 5.38.) Crack is the free-base (nonsalt) form of the alkaloid cocaine. It is called crack because, when heated, it makes a crackling sound. Heating crack enables a person to smoke it the drug is readily absorbed through the lungs and produces an intense euphoric effect in seconds Use has led to seizures and cardiac arrhythmias. Some of cocaine s effects (sympathomimetic) are due to blockade of norepinephrine reuptake into presynaptic terminals it does not block receptors. Flashbacks can occur with use of LSD and mescaline but have not been associated with the use of cocaine. 

S contemporary Mexican groups. Peyote contains more than 50 alkaloids, the most important of which is mescaline. 

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. 

Little is known specifically about the effects of mescaline compared to LSD. Much information about it relies upon its similarities with other monoamine hallucinogens. The majority of attention is given here to mescaline, but some brief mention of the diverse effects of other peyote alkaloids (of which little is known) is deserved. Often, their effects are very different from mescaline. Many alkaloids are present in sufficent concentrations to alter human physiology after oral consumption of peyote. Lophophorine in humans causes a "sickening feeling in the back of... 

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

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.

Figures 30-31) nuclei for alkaloids. Molecules containing nuclei from L-tyrosine include, for example, mescaline, anhalamine, papaverine, curare and morphine. They are biologically very strong natural compounds and occur relatively widely in the plant kingdom (Table 10). 

These alkaloids have a phenyl or phenylpropyl nucleus. The group includes simple phenyl amine (tyramine, hordenine), catecholamine (dopamine, noradrenaline, adrenaline), simple tetrahydroisoquinoline (mescaline, anhalamine, anhalonine, anhalonidine), benzylisoquinoline (e.g., papaverine), phthalideiso-quinoline (e.g., noscapine), phenethylisoquinoline (autumnaline, floramultine and kreysigine), tetrahydroisoquinoline (emehne and cephaeline) and terpenoid tetrahydroisoquinoline (secologanin and ipecoside) alkaloids. 

An alkaloid is a complex organic chemical substance found in plants, which characteristically combines nitrogen with other elements, has a bitter taste, and typically has some toxic, stimulant, analgesic effects. There are many different alkaloids, 30 of which are found in the opium plant. While morphine is the most important alkaloid in opium—for its natural narcotic qualities as well as providing the chemical structure for heroin—another alkaloid, codeine, is also sought after for its medicinal attributes. Other alkaloids include papaverine, narcotine, nicotine, atropine, cocaine, and mescaline. While the concentration of morphine in opium varies depending on where and how the plant is cultivated, it typically ranges from 3 percent to 20 percent. 

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). 

As you can see from Figure 23-1, alkaloids include compounds that may be classified as antimicrobial (quinine), as analgesics (morphine, codeine), as hallucinogens (mescaline, LSD), as stimulants (cocaine, atropine, caffeine),... 

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. 

Closely-related alkaloids cooccurring with mescaline are anhalamine, anhalonine, and anhalonidine (Figure 6.40), which are representatives of simple tetrahydroisoquinoline derivatives. 

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