Mescaline

Proposed Synthesis of MMDA and Mescaline by Rhodium and Osmium 980519... 

Mescaline a hallucinogenic amine obtained from the peyote cactus has been synthesized in two steps from 3 4 5 trimethoxybenzyl bromide The first step is nucleophilic substitution by sodium cyanide The second step is a lithium aluminum hydnde reduction What is the structure of mescaline" ... 

WATER - WATERPROOFING AND WATER/OIL REPELLENCY] (Vol 25) -mescaline in [POLYHYDROXY BENZENES] (Vol 19)... 

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,... 

Crude preparations of mescaline (61) from peyote were first reported by the Spanish as they learned of its use from the natives of Mexico during the Spanish invasion of that country in the sixteenth century. The colorful history (44) of mescaline has drawn attention to its use as a hallucinogen and even today it is in use among natives of North and South America. Although in connection with dmg abuse complaints, mescaline is considered dangerous, it has been reported (45) that it is not a narcotic nor is it habituating. It was also suggested that its sacramental use in the Native American Church of the United States be permitted since it appears to provoke only visual hallucination while the subject retains clear consciousness and awareness. 

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. 

Mescaline sulfate [2-(3,4,5-trimethoxyphenyI)ethyIamine sulfate] [5967-42-0] M 309.3, m 183-184°, pKesi -9.7. Crystd from water. 

Mezcaline (Mescaline), CnHijOjN, is a colourless alkaline oil, b.p. 180-180-5°/12 mm., which absorbs carbon dioxide from the air, forming a crystalline carbonate. The sulphate, Bj.HjSO4.2HjO, m.p. 183-6°, forms brilliant prisms the hydrochloride, m.p. 181°, coloirrless crystals picrate, m.p. 216-8° and the platinichloride (B. HCl)j. PtCl4, m.p. 

The term psychedelic literally means mind manifesting and was applied to hallucinogens like LSD or mescaline to emphasize the intensification of awareness and sensory perception that is associated with these drugs. 

Peyote/ mescaline Button(s), cactus, mesc, mescal, mescal buttons, moon, peyote... 

The phenylalkylamine hallucinogens show a close structural resemblance to the catecholamines, noradrenahne and dopamine. The prototype structure is found in mescaline, a naturally occurring substance. Modification of the mescaline molecule has led to synthetic amphetamine derivatives with hallucinogenic action. 

Peyote is ingested fresh (as whole dried buttons) or as powder (loose in capsules or pressed into tablets). Mescaline sold on the street (see Table 6—2) is generally not what it is claimed to be but is most likely one of the following DOM, PCP, LSD, caffeine, or amphetamine-related stimulants (Kulberg... 

The mode of action of the amphetamine derivatives MDA and MDMA seems to be dissimilar, with MDMA possessing mescaline-like psychoactive properties. MDMA demonstrates greater serotonergic effects than does the more amphetamine-like MDA. 

Mescaline is considerably less potent than LSD equipotent amounts are 5 mg and 1 pg, respectively. Peyote is readily absorbed from the gastrointestinal tract. Mescaline is mainly concentrated in the liver, spleen, and kidney. Up to 60% is excreted unchanged in the urine mescaline metabolites are devoid of any psychoactive effect. 

The lethal dose of mescaline varies because of the development of tolerance to the action of the drug. After a massive overdose, hypotension, bradycardia, CNS depression, and respiratory failure may be life threatening. Fatal intoxications from mescaline are rare, and fatalities associated with mescaline use are usually attributed to traumas resulting from altered perceptions. 

The active drug and metabolites can be detected from the urine by thin-layer chromatography, gas-liquid chromatography, or gas chromatography-mass spectrometry. However, assays are available only at specialized centers. Treatment of acute intoxication with mescaline is virtually identical to the treatment outlined for LSD intoxication. DOM-induced vasospasm responds well to intra-arterial tolazohne or sodium nitroprusside. Major life-threatening complications of hallucinogenic amphetamine derivatives include hyperthermia, hypertension, convulsions, cardiovascular collapse, and self-inflicted trauma. 

Paramethoxyamphetamine (PMA) has a hallucinogenic potency about five times that of mescaline and three times that of MDA. Because of its high toxicity, it caused fatal intoxications shortly after it became available on the street in the early 1970s (Cimbura 1974). Some of the fatalities were apparently due to the fact that the substance was sold to users as MDA because of the higher potency of PMA, severe intoxication (i.e., hypertensive crisis, seizures, death) occurred. 

Davis M Mescaline excitatory effects on acoustic startle are blocked by serotonin 2 antagonists. Psychopharmacology (Berl) 93 286—291, 1987 DishotskyNI, LoughamWD, Mogar RE, et al LSD and genetic damage. Science 172 431 40, 1971... 

Lyvers M, Hashing P Have Halpern et al. (2004) detected residual neuropsychological effects of MDMA not likely. Drug Alcohol Depend 75 149-152, 2004 Mack RB Marching to a different cactus peyote (mescaline) intoxication. N Engl J Med 47 137-138, 1986... 

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