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| {{SummarySheet}}
| | '''M''' |
| {{SubstanceBox/Mescaline}}
| | '''MESCALINE'''; 3,4,5-TRIMETHOXYPHENETHYLAMINE |
| '''3,4,5-Trimethoxyphenethylamine''' (also known as '''mescaline''') is a [[Naturally occurring sources|naturally-occurring]] classical [[Psychoactive class::psychedelic]] substance of the [[chemical class::phenethylamine]] class.<ref>{{cite journal|last=Nichols|first=David E.|author-link=David E. Nichols|doi-access=free|editor-last=Barker|editor-first=Eric L.|title=Psychedelics|journal=Pharmacological Reviews|volume=68|issue=2|pages=264-355|doi=10.1124/pr.115.011478|year=2016|issn=0031-6997|pmid=26841800|pmc=4813425|eissn=1521-0081|oclc=00824083}}</ref> It occurs naturally in the [[peyote]] cactus (''Lophophora williamsii''),<ref name="dib">{{cite book|title=Drug Identification Bible|location=Grand Junction, CO|publisher=Amera-Chem|year=2007|isbn=0-9635626-9-X|oclc=180867436}}</ref> San Pedro cactus (''[[Echinopsis pachanoi]]''),<ref>{{cite journal|url=http://catbull.com/alamut/Bibliothek/1973_d.m._crosby_8158_1.pdf|title=Cactus Alkaloids. XIX. Crystallization of Mescaline HCl and 3-Methoxytyramine HCl from Trichocereus pachanoi|pmid= 4773270|first1=D. M.|last1=Crosby|first2=J. L.|last2=McLaughlin|year=1973|volume=36|issue=4|pages=416-418|journal=Lloydia|issn=0024-5461|oclc=1606095}}</ref> Peruvian Torch cactus (''[[Echinopsis peruviana]]'') as well as the ''Cactaceae'' plant and the ''Fabaceae'' bean families.<ref>{{cite web|url=http://catbull.com/alamut/Bibliothek/chem%20of%20texas%20acacias.pdf|title=Chemistry of Acacia's from South Texas|publisher=Texas A&M Agricultural Research and Extension Center|last1=Forbes|first1=T. D. A.|last2=Clement|first2=B. A.|year=1998|location=Uvalde, Texas}}</ref> It is one of the oldest known [[hallucinogens]] and the parent compound of the psychedelic phenethylamines, one of the two major subclasses of psychedelic compounds (along with [[tryptamines]]). | |
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| Mescaline was first isolated from peyote in 1897 by the German chemist [[wikipedia:Arthur Heffter|Arthur Heffter]].<ref name="HeffterErowid">{{cite web|url=https://www.erowid.org/culture/characters/heffter_arthur/heffter_arthur.shtml|work=Erowid Character Vaults|date=August 9, 1998|access-date=September 30, 2020|title=Arthur Heffter}}</ref> The ritual use of the peyote cactus has occurred for at least 5700 years by Native Americans in Mexico and other mescaline-containing cacti such as the San Pedro have a long history of use in the South American continent, from Peru to Ecuador.<ref name="El-Seedi2005">{{cite journal|pmid=15990261|title=Prehistoric peyote use: Alkaloid analysis and radiocarbon dating of archaeological specimens of Lophophora from Texas|doi=10.1016/j.jep.2005.04.022|journal=Journal of Ethnopharmacology|volume=101|issue=1–3|year=2005|pages=238-242|first1=H. R.|last1=El-Seedi|first2=P. A. G. M.|last2=De Smet|first3=O.|last3=Beck|first4=G.|last4=Possnert|first5=J. G.|last5=Bruhn|issn=0378-8741|eissn=1872-7573|oclc=04649997}}</ref> Mescaline is an important part of the life's work of the American chemist [[Alexander Shulgin]], who used it as a starting point for synthesizing dozens of novel psychedelic compounds that are documented in his 1991 book [[PiHKAL]] ("Phenethylamines I Have Known and Loved").<ref name="PiHKAL">{{cite book|title=PiHKAL: A Chemical Love Story|title-link=PiHKAL|author-link1=Alexander Shulgin|author1=Alexander Shulgin|author2=Ann Shulgin|year=1991|publisher=Transform Press|location=United States|isbn=0963009605|oclc=1166889264|chapter-url=https://erowid.org/library/books_online/pihkal/pihkal096.shtml|chapter=#96. M}}</ref>
| | == SYNTHESIS == |
| | A solution of 20 g 3,4,5-trimethoxybenzaldehyde, 40 mL nitromethane, and 20 mL cyclohexylamine in 200 mL of acetic acid was heated on the steam bath for 1 h. The reaction mixture was then diluted slowly and with good stirring, with 400 mL H2O, which allowed the formation of a heavy yellow crystalline mass. This was removed by filtration, washed with H2O, and sucked as dry as possible. Recrystallization from boiling MeOH (15 mL/g) yielded, after filtration and air drying, beta-nitro-3,4,5-trimethoxystyrene as bright yellow crystals weighing 18.5 g. An alternate synthesis was effective, using an excess of nitromethane as solvent as well as reagent, if the amount of ammonium acetate catalysis was kept small. A solution of 20 g 3,4,5-trimethoxybenzaldehyde in 40 mL nitromethane containing 1 g anhydrous ammonium acetate was heated on the steam bath for 4 h. The solvent was stripped under vacuum and the residual yellow oil was dissolved in two volumes of hot MeOH, decanted from some insolubles, and allowed to cool. The crystals formed are removed by filtration, washed with MeOH and air dried yielding 14.2 g. of bright yellow crystals of beta-nitro-3,4,5-trimethoxystyrene. The use of these proportions but with 3.5 g ammonium acetate gave extensive side-reaction products even when worked up after only 1.5 h heating. The yield of nitrostyrene was, in this latter case, unsatisfactory. |
| | {{drugbox | |
| | | width = 200px |
| | | image = Mescaline.svg.png |
| | | image2 = Mescaline-3d-CPK.png |
| | | IUPAC_name = 2-(3,4,5-trimethoxyphenyl)ethanamine |
| | | CAS_number = 54-04-6 |
| | | CASNo_Ref = {{cascite}} |
| | | ChemSpiderID = 3934 |
| | | PubChem = 4076 |
| | | C=11 | H=17| N=1| O=3 |
| | | molecular_weight = 211.257 g/mol |
| | | melting_point = 35 |
| | | melting_high = 36 |
| | | melting_notes = (non-salt) |
| | | melting_point = 183 |
| | | melting_high = 186 |
| | | melting_notes = (Sulfate dihydrate) |
| | | synonyms = 3,4,5-trimethoxy-phenethylamine |
| | | smiles = NCCC1=CC(OC)=C(OC)C(OC)=C1 |
| | | elimination_half-life = |
| | | metabolism = |
| | | excretion = |
| | | pregnancy_category = |
| | | pregnancy_AU = X |
| | | pregnancy_US = X |
| | | legal_AU = Schedule 9 |
| | | legal_CA = Schedule III |
| | | legal_UK = Class A |
| | | legal_US = Schedule I |
| | | legal_status = |
| | | routes_of_administration = Oral, Intravenous}} |
| | To a gently refluxing suspension of 2 g LAH in 200 mL Et2O, there was added 2.4 g beta-nitro-3,4,5-trimethoxystyrene as a saturated Et2O solution by use of a Soxhlet extraction condenser modified to allow the continuous return of condensed solvent through the thimble. After the addition was complete, the refluxing conditions were maintained for another 48 h. After cooling the reaction mixture, a total of 150 mL of 1.5 N H2SO4 was cautiously added, destroying the excess hydride and untimately providing two clear phases. These were separated, and the aqueous phase was washed once with 50 mL Et2O. There was then added 50 g potassium sodium tartrate, followed by sufficient NaOH to bring the pH >9. This was then extracted with 3x75 mL CH2Cl2, and the solvent from the pooled extracts was removed under vacuum. The residue was distilled at 120-130 °C at 0.3 mm/Hg giving a white oil that was dissolved in 10 mL IPA and neutralized with concentrated HCl. The white crystals that formed were diluted with 25 mL Et2O, removed by filtration, and air dried to provide 2.1 g 3,4,5-trimethoxyphenethylamine hydrochloride (M) as glistening white crystals. The sulfate salt formed spectacular crystals from water, but had a broad and uncharacteristic mp. An alternate synthesis can employ 3,4,5-trimethoxyphenylacetonitrile, as described under beta-D. |
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| [[Subjective effects]] include [[geometry|open and closed-eye visuals]], [[time distortion]], [[introspection|enhanced introspection]], [[conceptual thinking]], [[euphoria]], and [[ego loss]]. Mescaline is generally considered to be one of the most gentle, insightful, and euphoric psychedelics. It is known for placing greater emphasis on bodily and tactile sensations (sometimes compared to [[MDMA]]) than [[tryptamines|psychedelic tryptamines]] like [[psilocybin]] or [[DMT]], which tend to have a more frenetic headspace and dynamic [[visual geometry]]. It is considered to be one of the best agents for psychedelic therapy due to its mellow, organic, yet complex character. Synthetic mescaline is highly sought after by connoisseurs and is typically produced in limited batches, owing to its low potency and relatively high production cost.
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| Unlike other highly prohibited substances, mescaline has not been proven to be physiologically toxic or addictive.<ref>{{cite journal|last1=Lüscher|first1=Christian|last2=Ungless|first2=Mark A.|title=The Mechanistic Classification of Addictive Drugs|year=2006|journal=PLOS Medicine|volume=3|issue=11|doi=10.1371/journal.pmed.0030437|doi-access=free|pmid=17105338|issn=1549-1277|pmc=1635740|eissn=1549-1676|oclc=54674092}}</ref> Nevertheless, adverse psychological reactions such as [[anxiety]], [[paranoia]], [[delusions]], and [[psychosis]] can still always occur, particularly among those predisposed to mental disorders.<ref>{{cite journal|last=Strassmann|first=Rick|title=Adverse reactions to psychedelic drugs. A review of the literature|journal=Journal of Nervous and Mental Disease|volume=172|issue=10|pages=577–595|doi=10.1097/00005053-198410000-00001|pmid=6384428|year=1984|issn=0022-3018|oclc=1754691}}</ref> Additionally, it should be noted that in street markets terms like "mescaline" or "synthetic mescaline" are commonly used as deceptive labels for other psychedelics (e.g. [[2C-x]], [[DOx]], or [[25x-NBOMe]]) that are typically more dangerous.{{citation needed}} It is highly advised to use [[harm reduction practices]] if using this substance.
| | == DOSAGE == |
| | 200-400 mg (as the sulfate salt), 178-356 mg (as the hydrochloride salt) [Erowid Note: The original text read "178-256" but this was an error. The error was found by Bo and verified with Shulgin. See the Erowid Mescaline Dosage page for a more complete discussion of the forms of mescaline]. |
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| ==History and culture==
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| The ritual use of the Peyote cactus has occurred for at least 5700 years by Native Americans in Mexico. Upon early contact, Europeans noted the use of Peyote in Native American religious ceremonies. Additionally, alternative mescaline-containing cacti such as the San Pedro have a long history of use in the South American continent, spanning from Peru to Ecuador.<ref name="El-Seedi2005" />
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| The principal psychoactive component in both Peyote and San Pedro, mescaline, was first isolated and identified in 1897 by the German chemist Arthur Heffter<ref name="HeffterErowid" /> and first synthesized in 1919 by Ernst Späth.<ref>{{cite book|chapter-url=https://www.erowid.org/archive/rhodium/chemistry/mescaline.alkaloids.html|title=The Alkaloids|chapter=Mescaline (3,4,5-Trimethoxyphenethylamine)|location=New York|publisher=Academic Press|year=1953|first1=R. H. F.|last1=Manske|first2=H. L.|last2=Holmes|isbn=0080865275|oclc=281698426|volume=III|pages=324-328}}</ref> It was one of the first psychedelics to be experimented with by Western intellectuals like Aldous Huxley, who famously described its effects in the 1954 essay "The Doors of Perception".{{citation needed}}
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| In traditional peyote preparations, the top of the cactus is cut at ground level, leaving the large tap roots to grow new 'heads'. These 'heads' are then dried to make disc-shaped buttons and the buttons are chewed to produce the effects or soaked in water to drink. In modern times, users will often grind it into a powder and pour it into gel capsules to avoid having to come into contact with the bitter taste of the cactus. The usual human dose is 200–400 milligrams of mescaline sulfate or 178–356 milligrams of mescaline hydrochloride.<ref name="PiHKAL">{{cite book|title=PiHKAL: A Chemical Love Story|title-link=PiHKAL|author-link1=Alexander Shulgin|author1=Alexander Shulgin|author2=Ann Shulgin|year=1991|publisher=Transform Press|location=United States|isbn=0963009605|oclc=1166889264|chapter-url=https://erowid.org/library/books_online/pihkal/pihkal096.shtml|chapter=#96. M}}</ref> The average 76 mm (3.0 in.) button contains about 25 mg mescaline.<ref>{{cite book|first1=A. J.|last1=Giannini|first2=A. E.|last2=Slaby|first3=M. C.|last3=Giannini|year=1982|title=Handbook of Overdose and Detoxification Emergencies|location=New Hyde Park, NY|publisher=Medical Examination Publishing Company|isbn=978-0-87488-182-0|oclc=9084341}}</ref>
| | == DURATION == |
| | 10-12 h |
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| Mescaline is an important part of the life's work of [[Alexander Shulgin]], a psychedelic chemist and researcher. Shulgin used mescaline as a starting point for synthesizing dozens of novel psychedelic phenethylamine compounds such as the [[2C-x]] and [[DOx]] families. It is a member of the so-called "magical half-dozen" which refers to Shulgin's self-rated most important phenethylamine compounds with psychedelic activity, all of which except mescaline he developed and synthesized himself. They are found within the first book of [[PiHKAL]], and are as follows: Mescaline, [[DOM]], [[2C-B]], [[2C-E]], [[2C-T-2]] and [[2C-T-7]].<ref>{{cite book|title=PiHKAL: A Chemical Love Story|author-link1=Alexander Shulgin|author1=Alexander Shulgin|author2=Ann Shulgin|year=1991|publisher=Transform Press|location=United States|isbn=0963009605|oclc=1166889264|url=https://erowid.org/library/books_online/pihkal/pihkal.shtml}}</ref>
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| ==Chemistry== | | == QUALITATIVE COMMENTS == |
| Mescaline, or 3,4,5-trimethoxyphenethylamine, is a substituted [[phenethylamines|phenethylamine]] featuring a phenyl ring bound to an amino -NH<sub>2</sub> group through an ethyl chain. Mescaline contains three methoxy functional groups CH<sub>3</sub>O- which are attached to carbons R<sub>3</sub>, R<sub>4</sub>, and R<sub>5</sub> of the phenyl ring.
| | (with 300 mg) I would have liked to, and was expecting to, have an exciting visual day, but I seemed to be unable to escape self-analysis. At the peak of the experience I was quite intoxicated and hyper with energy, so that it was not hard to move around. I was quite restless. But I spent most of the day in considerable agony, attempting to break through without success. I learned a great deal about myself and my inner workings. Everything almost was, but in the final analysis, wasn't. I began to become aware of a point, a brilliant white light, that seemed to be where God was entering, and it was inconceivably wonderful to perceive it and to be close to it. One wished for it to approach with all one's heart. I could see that people would sit and meditate for hours on end just in the hope that this little bit of light would contact them. I begged for it to continue and come closer but it did not. It faded away not to return in that particular guise the rest of the day. Listening to Mozart's Requiem, there were magnificent heights of beauty and glory. The world was so far away from God, and nothing was more important than getting back in touch with Him. But I saw how we created the nuclear fiasco to threaten the existence of the planet, as if it would be only through the threat of complete annihilation that people might wake up and begin to become concerned about each other. And so also with the famines in Africa. Many similar scenes of joy and despair kept me in balance. I ended up the experience in a very peaceful space, feeling that though I had been through a lot, I had accomplished a great deal. I felt wonderful, free, and clear. |
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| Mescaline has a number of structural analogs, which include but are not limited to: [[proscaline]], [[escaline]], and [[methallylescaline]]. It is also the synthetic starting point of the [[2C-x]] and [[DOx]] family of psychedelic phenethylamines. 2C-x compounds like [[2C-B]] (also known as bromomescaline) produce mescaline-like psychedelic effects but with greater potency and a reduced duration. DOx compounds (e.g. [[DOM]], [[DOB]]) have a significantly extended duration and more stimulant effects.
| | (with 350 mg) Once I got through the nausea stage, I ventured out-of-doors and I was aware of an intensification of color and a considerable change in the texture of the cloth of my skirt and in the concrete of the sidewalk, and in the flowers and leaves that were handed me by an observer. I experienced the desire to laugh hysterically at what I could only describe as the completely ridiculous state of the entire world. Although I was afraid of motion, I was persuaded to take a ride in a car. The driver turned on the radio and suddenly the music 'The March of the Siamese Children' from 'The King and I' became the most perfect background music for the parody of real life which was indeed the normal activity of Telegraph Avenue on any Saturday morning. The perfectly ordinary people on their perfectly ordinary errands were clearly the most cleverly contrived set of characters all performing all manners of eccentric activities for our particular hilarity and enjoyment. I felt that I was at the same time both observing and performing in an outrageous moving picture. I experienced one moment of transcendant happiness when, while passing Epworth Hall, I looked out of the window of the car and up at the building and I was suddenly in Italy looking up at a gay apartment building with its shutters flung open in sunshine, and with its window boxes with flowers. We stopped at a spot overlooking the bay, but I found the view uninteresting and the sun uncomfortable. I sat there on the seat of the car looking down at the ground, and the earth became a mosaic of beautiful stones which had been placed in an intricate design which soon all began to move in a serpentine manner. Then I became aware that I was looking at the skin of a beautiful snake--all the ground around me was this same huge creature and we were all standing on the back of this gigantic and beautiful reptile. The experience was very pleasing and I felt no revulsion. Just then, another automobile stopped to look at the view and I experienced my first real feeling of persecution and I wanted very much to leave. |
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| ==Pharmacology==
| | (with 400 mg) During the initial phase of the intoxication (between 2 and 3 hours) everything seemed to have a humorous interpretation. People's faces are in caricature, small cars seem to be chasing big cars, and all cars coming towards me seem to have faces. This one is a duchess moving in regal pomp, that one is a wizened old man running away from someone. A remarkable effect of this drug is the extreme empathy felt for all small things; a stone, a flower, an insect. I believe that it would be impossible to harm anything--to commit an overt harmful or painful act on anyone or anything is beyond one's capabilities. One cannot pluck a flower--and even to walk upon a gravel path requires one to pick his footing carefully, to avoid hurting or disturbing the stones. I found the color perception to be the most striking aspect of the experience. The slightest difference of shade could be amplified to extreme contrast. Many subtle hues became phosphorescent in intensity. Saturated colors were often unchanged, but they were surrounded by cascades of new colors tumbling over the edges. |
| {{Further|Serotonergic psychedelic}}
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| Mescaline acts similarly to other psychedelic agents.<ref name="hallucinogens">{{cite journal|last1=Nichols|first1=David E.|author-link=David E. Nichols|year=2004|title=Hallucinogens|journal=Pharmacology & Therapeutics|volume=101|issue=2|pmid=14761703|pages=131-181|doi=10.1016/j.pharmthera.2003.11.002|issn=0163-7258|eissn=1879-016X|oclc=04981366}}</ref> It binds to and activates the serotonin 5-HT<sub>2A</sub> receptor with a high affinity.<ref>{{cite journal|pmid=9301661|title=Dihydrobenzofuran Analogues of Hallucinogens. 4. Mescaline Derivatives|first1=A. P.|last1=Monte|first2=S. R.|last2=Waldman|first3=D.|last3=Marona-Lewicka|first4=D. B.|last4=Wainscott|first5=D. L.|last5=Nelson|first6=E.|last6=Sanders-Bush|first7=D. E.|last7=Nichols|author-link7=David E. Nichols|journal=Journal of Medicinal Chemistry|year=1997|volume=40|issue=19|pages=2997–3008|doi=10.1021/jm970219x|issn=0022-2623|eissn=1520-4804|oclc=39480771}}</ref> How activating the 5-HT<sub>2A</sub> receptor leads to psychedelia is still unknown, but it likely somehow involves excitation of neurons in the prefrontal cortex.<ref>{{cite journal|pmid=17535909|title=Mechanism of the 5-hydroxytryptamine 2A receptor-mediated facilitation of synaptic activity in prefrontal cortex|pmc=1887564|doi-access=free|doi=10.1073/pnas.0700436104|first1=J.-C.|last1=Béïque|first2=M.|last2=Imad|first3=L.|last3=Mladenovic|first4=J. A.|last4=Gingrich|first5=R.|last5=Andrade|year=2007|volume=104|issue=23|pages=9870-9875|journal=Proceedings of the National Academy of Sciences of the United States of America|issn=0027-8424|eissn=1091-6490|oclc=43473694}}</ref> Mescaline is also known to bind to and activate the serotonin 5-HT2C receptor.<ref>{{cite web|url=https://www.erowid.org/psychoactives/pharmacology/pharmacology_article1.shtml|title=The Neuropharmacology of Hallucinogens: a brief introduction|author="BILZoR"|publisher=Erowid|version=v1|date=February 2004|access-date=September 30, 2020}}</ref>
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| ==Subjective effects==
| | (with 400 mg) It took a long time to come on and I was afraid that I had done it wrong but my concerns were soon ended. The world soon became transformed where objects glowed as if from an inner illumination and my body sprang to life. The sense of my body, being alive in my muscles and sinews, filled me with enormous joy. I watched Ermina fill to brimming with animal spirit, her features tranformed, her body cat-like in her graceful natural movement. I was stopped in my tracks. The world seemed to hold its breath as the cat changed again into the Goddess. As she shed her clothes, she shed her ego and when the dance began, Ermina was no more. There was only the dance without the slightest self-consconciousness. How can anything so beautiful be chained and changed by other's expectations? I became aware of myself in her and as we looked deeply into one another my boundaries disappeared and I became her looking at me. |
| {{Preamble/SubjectiveEffects}}
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| {{effects/base
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| |{{effects/physical|
| | == EXTENSIONS AND COMMENTARY == |
| | Mescaline is one of the oldest [[psychedelics]] known to man. It is the major active component of the small dumpling cactus known as Peyote. It grows wild in the Southwestern United States and in Northern Mexico, and has been used as an intimate component of a number of religious traditions amongst the native Indians of these areas. The cactus has the botanical name of Lophophora williamsii or Anhalonium lewinii and is immediately recognizable by its small round shape and the appearance of tufts of soft fuzz in place of the more conventional spines. The dried plant material has been classically used with anywhere from a few to a couple of dozen of the hard tops, called buttons, being consumed in the course of a ceremony. |
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| *'''[[Effect::Stimulation]]''' - Mescaline is usually considered to be very energetic and stimulating without being forced. For example, when taken in any environment it will usually encourage physical activities such as running, walking, climbing or dancing. In comparison, other more commonly used psychedelics such as [[psilocin]] are generally sedating and relaxed.
| | Throughout the more recently published record of clinical human studies with mescaline, it has been used in the form of the synthetic material, and has usually been administered as the sulfate salt. Although this form has a miserable melting point (it contains water of crystallization, and the exact melting point depends on the rate of heating of the sample) it nonetheless forms magnificent crystals from water. Long, glistening needles that are, in a sense, its signature and its mark of purity. The dosages associated with the above "qualitative comments" are given as if measured as the sulfate, although the actual form used was usually the hydrochloride salt. The conversion factor is given under "dosage" above. |
| *'''[[Effect::Spontaneous bodily sensations]]''' - The "body high" of mescaline can be described as proportionally intense in comparison to its accompanying visual and cognitive effects. It is manifested in a number of forms including an intense soft, warm glow that grows over the body and is capable of becoming extremely physically [[Effect::physical euphoria|euphoric]]. This is most similar to [[MDMA]] and [[psilocin]] and is consistently manifested throughout the experience. This is contrasted by an intensely pleasurable yet sharp, cold electric tingling sensation which moves up and down the body. This is most similar to [[LSD]] and is also consistently manifested throughout the experience. The final physical effect noticed throughout the experience is an intense energetic pins and needles sensation that manifests itself in the form of a continuously shifting and tingling sensation that travels up and down the body in spontaneous waves. This is most similar to [[2C-B]] and is not entirely consistent throughout the experience.
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| **'''[[Effect::Physical euphoria]]''' - Relative to other psychedelics, mescaline has been noted for the bodily or physically euphoric aspect that is vaguely reminiscent of other [[phenethylamines]] like [[MDA]].
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| *'''[[Effect::Nausea]]''' - Nausea is commonly reported when consumed in moderate to high doses and either passes instantly once the user has vomited or gradually fades by itself as the peak sets in.
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| *'''[[Effect::Increased salivation]]''' - This effect, while uncommon, seems to be less pronounced than it is with [[psilocin]] and other tryptamines and usually does not persist throughout the experience.
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| *'''[[Effect::Tactile enhancement]]''' - Feelings of enhanced tactile sensations are consistently present at moderate levels. If [[Effect::8A Geometry|Level 8A geometry]] is reached, an intense sensation of suddenly becoming aware of and being able to feel every single nerve ending across a person's entire body all at once is consistently present.
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| *'''[[Effect::Appetite suppression]]'''
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| *'''[[Effect::Bodily control enhancement]]'''
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| *'''[[Effect::Stamina enhancement]]'''
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| *'''[[Effect::Olfactory enhancement]]'''
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| *'''[[Effect::Frequent urination]]'''
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| *'''[[Effect::Increased heart rate]]'''
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| *'''[[Effect::Increased libido]]'''
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| *'''[[Effect::Muscle contractions]]'''
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| *'''[[Effect::Pupil dilation]]'''
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| *'''[[Effect::Seizure]]''' - A rarely observed effect but is thought to be able to happen in those predisposed to them, especially while in physically taxing conditions such as being dehydrated, fatigued, undernourished, or overheated.{{citation needed}}
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| | Mescaline has always been the central standard against which all other compounds are viewed. Even the United States Chemical Warfare group, in their human studies of a number of substituted phenethylamines, used mescaline as the reference material for both quantitative and qualitative comparisons. The Edgewood Arsenal code number for it was EA-1306. All psychedelics are given properties that are something like "twice the potency of mescaline" or "twice as long-lived as mescaline." This simple drug is truly the central prototype against which everything else is measured. The earliest studies with the "psychotomimetic amphetamines" had quantitative psychological numbers attached that read as "mescaline units." Mescaline was cast in concrete as being active at the 3.75 mg/kg level. That means for a 80 kilogram person (a 170 pound person) a dose of 300 milligrams. If a new compound proved to be active at 30 milligrams, there was a M.U. level of 10 put into the published literature. The behavioral biologists were happy, because now they had numbers to represent psychological properties. But in truth, none of this represented the magic of this material, the nature of the experience itself. That is why, in this Book II, there is only one line given to "dosage," but a full page given to "qualitative comments". |
| {{effects/visual|
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| ====Enhancements====
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| *'''[[Effect::Colour enhancement]]'''
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| *'''[[Effect::Pattern recognition enhancement]]'''
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| *'''[[Effect::Visual acuity enhancement]]'''
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| ====Distortions====
| | Four simple N-modified mescaline analogues are of interest in that they are natural and have been explored in man. |
| *'''[[Effect::Drifting]]''' ''([[Drifting#Melting|melting]], [[Drifting#Flowing|flowing]], [[Drifting#Breathing|breathing]] and [[Drifting# morphing|morphing]])'' - In comparison to other psychedelics, this effect can be described as highly detailed, slow and smooth in motion, static in appearance and realistic in style.
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| *'''[[Effect::After images]]'''
| |
| *'''[[Effect::Colour shifting]]'''
| |
| *'''[[Effect::Recursion]]'''
| |
| *'''[[Effect::Scenery slicing]]'''
| |
| *'''[[Effect::Symmetrical texture repetition]]'''
| |
| *'''[[Effect::Tracers]]'''
| |
|
| |
|
| ====[[Effect::Geometry]]====
| | The N-acetyl analogue has been found in the peyote plant, and it is also a major metabolite of mescaline in man. It is made by the gentle reaction of mescaline with acetic anhydride (a bit too much heat, and the product N-acetyl mescaline will cyclize to a dihydroisoquinoline, itself a fine white crystalline solid, mp 160-161 °C) and can be recrystallized from boiling toluene. A number of human trials with this amide at levels in the 300 to 750 milligrams range have shown it to be with very little activity. At the highest levels there have been suggestions of drowsiness. Certainly there were none of the classic mescaline psychedelic effects. |
| The visual geometry encountered on mescaline can be described as similar in appearance to that of [[ayahuasca]], [[2C-P]] or [[psilocin]] in the sense that its geometry is structured in its organization as well as natural and organic in style. However, in terms of its bright colors, sharp edges and angular corners, it is more similar to that of [[LSD]], [[2C-B]] and [[2C-I]]. | |
|
| |
|
| The geometry can be comprehensively described as:
| | If free base mescaline is brought into reaction with ethyl formate (to produce the amide, N-formylmescaline) and subsequently reduced (with lithium aluminum hydride) it is converted to the N-methyl homologue. This base has also been found as a trace component in the Peyote cactus. And the effects of N-methylation of other psychedelic drugs have been commented upon elsewhere in these recipes, all with consistently negative results (with the noteworthy exception of the conversion of MDA to MDMA). Here, too, there is no obvious activity in man, although the levels assayed were only up to 25 milligrams. |
|
| |
|
| *'''[[Geometry#Organic_vs._synthetic|Organic in geometric style]]'''
| | N,N-Dimethylmescaline has been given the trivial name of Trichocerine as it has been found as a natural product in several cacti of the Trichocereus Genus but, interestingly, never in any Peyote variant. It also has proven inactive in man in dosages in excess of 500 milligrams, administered parenterally. This observation, the absence of activity of a simple tertiary amine, has been exploited in the development of several iodinated radiopharmaceuticals that are mentioned elsewhere in this book. |
| *'''[[Geometry#Algorithmic_vs._abstract|Equally abstract and algorithmic in appearance]]'''
| |
| *'''[[Geometry#Intricate_vs._simplistic|Intricate in complexity]]'''
| |
| *'''[[Geometry#Unstructured_vs._structured|Structured in its organization]]'''
| |
| *'''[[Geometry#Fast_vs._slow|Fast in speed]]'''
| |
| *'''[[Geometry#Smooth_vs._jittery|Smooth in motion]]'''
| |
| *'''[[Geometry#Large_vs._small|Equally large and small in appearance]]''' - It has a variable size that spontaneously changes between large and small in appearance.
| |
| *'''[[Geometry#Multicoloured_vs._monotone|Multicoloured in scheme]]'''
| |
| *'''[[Geometry#Flat shading_vs._glossy_shading|Glossy in colour]]'''
| |
| *'''[[Geometry#Sharp_edges_vs._soft edges|Sharp and angular in its corners]]'''
| |
| *'''[[Geometry#Level_8A_vs._level_8B|Level 8B]]''' - While the geometry produced by mescaline has yet to be fully characterized, the geometry gives off certain attributes which are significantly more likely to result in states of [[level 8A]] visual geometry over [[level 8B]] at higher doses.
| |
|
| |
|
| ====Hallucinatory states====
| | The fourth modification is the compound with the nitrogen atom oxidatively removed from the scene. This is the mescaline metabolite, 3,4,5-trimethoxyphenylacetic acid, or TMPEA. Human dosages up to 750 milligrams orally failed to produce either physiological or psychological changes. |
| Mescaline is capable of producing a full range of high-level hallucinatory states in a fashion that is more consistent and reproducible than that of many other commonly used psychedelics.
| |
|
| |
|
| *'''[[Effect::Transformations]]'''
| | One additional manipulation with some of these structures has been made and should be mentioned. These are the analogues with an oxygen atom inserted between the aromatic ring and the aliphatic chain. They are, in essence, aminoethyl phenyl ethers. The first is related to mescaline itself, 2-(3,4,5-trimethoxyphenoxy)ethylamine. Human trials were conducted over the dose range of 10 to 300 milligrams and there were no effects observed. The second is related to trichocerine, N,N-dimethyl-2-(3,4,5-trimethoxyphenoxy)ethylamine. It was inactive in man over the range of 10 to 400 milligrams. Mescaline, at a dose of 420 milligrams, served as the control in these studies. |
| *'''[[Effect::Internal hallucination]]''' (''[[Effect::autonomous entities]]''; ''[[Effect::settings, sceneries, and landscapes]]''; ''[[Effect::perspective hallucinations]]'' and ''[[Effect::scenarios and plots]]'') - In comparison to other psychedelics such as [[LSD]], mescaline produces a high level of hallucinations embedded within visual [[geometry]]. This particular effect commonly contains hallucinations with scenarios, settings, concepts and [[Effect::autonomous entities|autonomous entity contact]]. They are more common within dark environments and can be described as lucid in believability, interactive in style and almost exclusively of a personal, religious, spiritual, science-fiction, fantasy, surreal, nonsensical or transcendental nature in their overall theme.
| | [[Category:Drugs]] |
| *'''[[Effect::External hallucination]]''' (''[[Effect::autonomous entities]]''; ''[[Effect::settings, sceneries, and landscapes]]''; ''[[Effect::perspective hallucinations]]'' and ''[[Effect::scenarios and plots]]'')
| | [[Category:PiHKAL]] |
| }}
| | [[Category:Shulgin]] |
| |{{effects/cognitive|
| |
|
| |
|
| In comparison to other psychedelics such as [[psilocin]], [[LSA]] and [[ayahuasca]], mescaline is significantly more stimulating and fast-paced in terms of the specific style of thought stream produced and contains a large number of potential effects.
| | {{PiHKAL}} |
| | |
| *'''[[Effect::Analysis enhancement]]''' - This effect is consistent in its manifestation and [[Outrospection|outrospection]] dominant.
| |
| *'''[[Effect::Cognitive euphoria]]'''
| |
| *'''[[Effect::Conceptual thinking]]'''
| |
| *'''[[Effect::Creativity enhancement]]'''
| |
| *'''[[Effect::Delusion]]'''
| |
| *'''[[Effect::Emotion enhancement]]'''
| |
| *'''[[Effect::Empathy, love, and sociability enhancement]]''' - This is commonly reported as being similar to but less prominent than with other commonly used [[entactogen]]s such as [[MDMA]] or [[MDA]].
| |
| *'''[[Effect::Euthymia]]''' - This effect manifests itself acutely for all classical psychedelics when one to three doses are combined with a psychotherapy treatment program. When comparing meta analyses, psychedelic psychotherapy greatly outperforms "gold standard" treatments for several mental health problems.
| |
| *'''[[Effect::Focus enhancement]]''' - This effect is experienced exclusively on low or threshold dosages and feels less forced or sharp than it does with traditional stimulants.
| |
| *'''[[Effect::Immersion enhancement]]'''
| |
| *'''[[Effect::Increased music appreciation]]'''
| |
| *'''[[Effect::Memory suppression]]'''
| |
| **'''[[Effect::Ego death]]''' - This component is less consistent and obtainable when compared to other more common psychedelics such as [[psilocin]] or [[LSD]]. In mescaline's case this effect is highly dose dependent and is also fairly contingent upon the individual's [[set and setting]].
| |
| *'''[[Effect::Motivation enhancement]]''' - This effect feels less forced or prominent than it does with traditional [[stimulants]].
| |
| *'''[[Effect::Novelty enhancement]]'''
| |
| *'''[[Effect::Personal bias suppression]]'''
| |
| *'''[[Effect::Personal meaning enhancement]]'''
| |
| *'''[[Effect::Autonomous voice communication]]''' - This effect is generally reported as being mild in comparison to tryptamines such as [[DMT]] and its related analogs.
| |
| *'''[[Effect::Suggestibility enhancement]]'''
| |
| *'''[[Effect::Thought acceleration]]'''
| |
| *'''[[Effect::Thought connectivity]]''' - Due to its mostly lucid headspace this component is significantly less intense in relation to [[psilocybin]].
| |
| *'''[[Effect::Thought loops]]'''
| |
| *'''[[Effect::Time distortion]]'''
| |
| *'''[[Effect::Wakefulness]]'''
| |
| | |
| }}
| |
| {{effects/auditory|
| |
| | |
| *'''[[Effect::Auditory enhancement|Enhancements]]'''
| |
| *'''[[Effect::Auditory distortion|Distortions]]'''
| |
| *'''[[Effect::Auditory hallucinations|Hallucinations]]'''
| |
| | |
| }}
| |
| {{effects/multisensory| | |
| | |
| *'''[[Effect::Synaesthesia]]''' - In its fullest manifestation, this is a very rare and non-reproducible effect. Increasing the dosage can increase the likelihood of this occurring, but seems to only be a prominent part of the experience among those who are already predisposed to synaesthetic states.
| |
| | |
| }}
| |
| {{effects/transpersonal|
| |
| | |
| *'''[[Effect::Spirituality enhancement]]'''
| |
| *'''[[Effect::Existential self-realization]]''' - This effect is typically more prevalent in high doses, but can also occur at common doses as well. For a number of users this effect is less repeatable than it is with traditional [[tryptamines]] such as [[psilocin]].
| |
| *'''[[Effect::Unity and interconnectedness]]'''
| |
| | |
| }}
| |
| }}
| |
| ===Experience reports===
| |
| Anecdotal reports which describe the effects of this compound within our [[experience index]] include:
| |
| {{#ask: [[Category:Mescaline]][[Category:Experience]]|format=ul|Columns=1}}
| |
| Additional experience reports can be found here:
| |
| | |
| *[https://erowid.org/experiences/subs/exp_Mescaline.shtml Erowid Experience Vaults: Mescaline]
| |
| | |
| ==Natural sources==
| |
| [[File:Flowering San Pedro cactus.jpg|270px|thumbnail|right|Flowering San Pedro, an entheogenic cactus that has been used for over 3,000 years<ref>{{cite book|chapter-url=http://www.mescaline.com/sanpedro/|chapter=San Pedro Cactus|author=Richard Rudgley|year=1998|title=The Encyclopedia of Psychoactive Substances|publisher=Little, Brown and Company|location=London|isbn=0316643475}}</ref>]]
| |
| | |
| *''[[Lophophora williamsii]]'' (''Peyote''), Mescaline 0.4%<ref name="guide">{{cite web|url=http://www.erowid.org/plants/cacti/cacti_guide/cacti_guide_lophopho.shtml|publisher=Erowid|accessdate=January 14, 2015|title=Visionary Cactus Guide: Cactus Botany}}</ref> - Mescaline 3-6%<ref name="guide" /><ref name="cactuschemistry">{{cite web|url=http://sacredcacti.com/wp-content/uploads/2015/02/CactusChemistryBySpecies_2014_Light.pdf|title=Cactus Chemistry By Species|author=Keeper Trout & friends|archive-url=http://web.archive.org/web/20160711010059/http://sacredcacti.com/wp-content/uploads/2015/02/CactusChemistryBySpecies_2014_Light.pdf|archive-date=July 11, 2016|year=2014|publisher=Mydriatic Productions}}</ref>
| |
| *''[[Lophophora diffusa]]'' Hordenine 0.5% of total alkaloid, N-Methyltyramine 0.1% of total alkaloid, Mescaline (trace) <ref name="cactuschemistry" />
| |
| *''[[Echinopsis pachanoi]]'' (syn. ''Trichocereus pachanoi''), Mescaline 0.006-0.12%, 0.05% Average<ref name="netfirms" /> - Mescaline 0.01%-2.375%<ref name="netfirms" />
| |
| *''[[Echinopsis peruviana]]'' (syn. ''Trichocereus peruvianus''), Mescaline 0.0005%-0.12%<ref name="netfirms">{{cite web|url=http://entheogen.netfirms.com/articles/articles/Narcotic_Cacti.html|work=Forbidden Fruit Archives|archive-url=https://web.archive.org/web/20080512012309/entheogen.netfirms.com/articles/articles/Narcotic_Cacti.html|archive-date=May 12, 2008|title=Narcotic and Hallucinogenic Cacti of the New World|author=Michael S. Smith|date=June 1998}}</ref>
| |
| *''[[Echinopsis lageniformis]]'' (syn. ''Trichocereus bridgesii'' aka ''Bolivian torch''), Mescaline 0.025%,<ref name="nook2">{{cite web|url=http://www.thenook.org/archives/tek/alklist.htm |title=Partial List of Alkaloids in Trichocereus Cacti |publisher=The Nook|archive-url=http://web.archive.org/web/20191230071125/http://www.thenook.org/archives/tek/alklist.htm|archive-date=December 30, 2019}}</ref> also 3,4-Dimethoxyphenylethylamine 1%, 3-Methoxytyramine 1%, Tyramine 1% - Mescaline 2%<ref>{{cite web|url=http://www.a1b2c3.com/drugs/var014.htm|title=Trichocereus spp.|publisher=a1b2c3.com|access-date=September 30, 2020}}</ref>
| |
| *''[[Echinopsis scopulicola]]'' (syn. ''Trichocereus scopulicola''), Mescaline<ref name="guide" />
| |
| *''[[Echinopsis spachiana]]'' (syn. ''Trichocereus spachianus''), Mescaline<ref name="guide" /> - Mescaline<ref name="guide" />
| |
| *''[[Echinopsis macrogona]]'' (syn. ''Trichocereus macrogonus''), Mescaline 0.01-0.05%<ref name="nook2" />
| |
| *''[[Echinopsis tacaquirensis]]'' subsp. ''taquimbalensis'' (syn. ''Trichocereus taquimbalensis''),<ref>{{cite web|url=http://www.desert-tropicals.com/Plants/Cactaceae/Echinopsis_taquimb.html|title=Echinopsis tacaquirensis ssp. taquimbalensis|publisher=Desert Tropicals|accessdate=14 January 2015}}{{dead link|date=September 2020}}</ref> 0.005-0.025% Mescaline<ref name="nook2" />
| |
| *''[[Echinopsis terscheckii]]'' (syn. ''Trichocereus terscheckii'', ''Trichocereus werdemannianus'')<ref>{{cite web|url=http://www.desert-tropicals.com/Plants/Cactaceae/Echinopsis_terscheckii.html|title=Cardon Grande (Echinopsis terscheckii)|publisher=Desert Tropicals|accessdate=14 January 2015}}{{dead link|date=September 2020}}</ref> Mescaline 0.005-0.025%<ref name="nook2" /> - Mescaline 0.01%-2.375%<ref name="netfirms" />
| |
| *''[[Echinopsis valida]]'', Mescaline 0.025%<ref name="guide" />
| |
| *''[[Opuntia acanthocarpa]]'', Mescaline<ref name="guide" />
| |
| *''[[Opuntia basilaris]]'', Mescaline 0.01%, plus 4-hydroxy-3-5-dimethoxyphenethylamine<ref name="guide" />
| |
| *''[[Austrocylindropuntia cylindrica]]'' (syn. ''Opuntia cylindrica'')<ref>{{cite web|url=http://www.desert-tropicals.com/Plants/Cactaceae/Opuntia_cylindrica.html|title=Austrocylindropuntia cylindrica|publisher=Desert Tropicals}}{{dead link|date=September 2020}}</ref> Mescaline<ref name="guide" />
| |
| *''[[Cylindropuntia echinocarpa]]'' (syn. ''Opuntia echinocarpa''), Mescaline 0.01%, 3-4-Dimethoxyphenethylamine 0.01%, 4-Hydroxy-3-5-Dimethoxyphenethylamine 0.01%<ref name="guide" />
| |
| *''[[Cylindropuntia spinosior]]'' (syn. ''Opuntia spinosior''), Mescaline 0.00004% <ref>{{cite web|url=http://www.desert-tropicals.com/Plants/Cactaceae/Opuntia_spinosior.html|title=Cane Cholla|author=Philippe Faucon|publisher=Desert-Tropicals|archive-url=https://web.archive.org/web/20190109104049/http://www.desert-tropicals.com/Plants/Cactaceae/Opuntia_spinosior.html|archive-date=January 9, 2019}}</ref> Mescaline 0.00004%, 3-Methoxytyramine 0.001%, Tyramine 0.002%, 3-4-Dimethoxyphenethylamine.<ref name="guide" />
| |
| *''[[Pelecyphora aselliformis]]'', Hordenine, Mescaline (trace) <ref name="cactuschemistry" />
| |
| | |
| ==Toxicity and harm potential==
| |
| {{Further|Responsible use#Hallucinogens}}
| |
| The toxicity and long-term health effects of recreational mescaline use does not appear to have been studied in any scientific context and the exact [[Toxicity::toxic dose is unknown]]. However, there are no known fatal overdoses within the scientific literature.
| |
| | |
| Anecdotal reports suggest that there are no negative health effects attributed to simply trying mescaline by itself at low to moderate doses and using it very sparingly (but nothing can be completely guaranteed).
| |
| | |
| [https://www.google.com/ Independent research] should always be done to ensure that a combination of two or more substances is safe before consumption.
| |
| | |
| It is strongly recommended that one use [[harm reduction practices]] when using this substance.
| |
| ===Dependence and abuse potential===
| |
| Mescaline is [[Addiction potential::not habit-forming]], and the desire to use it can actually decrease with use. It is most often self-regulating.
| |
| | |
| Tolerance to the effects of mescaline is built [[Time to full tolerance::almost immediately after ingestion]]. After that, it takes about [[Time to half tolerance::3 days]] for the tolerance to be reduced to half and [[Time to zero tolerance::7 days]] to be back at baseline (in the absence of further consumption). Mescaline presents cross-tolerance with [[Cross-tolerance::all [[psychedelic]]s]], meaning that after the consumption of mescaline all psychedelics will have a reduced effect.<ref>{{cite web|title=Psychedelics and Society|author=Michael Valentine Smith|url=https://www.erowid.org/archive/rhodium/chemistry/psychedelicchemistry/chapter1.html|access-date=September 30, 2020|publisher=Erowid|work=Psychedelic Chemistry}}</ref>
| |
| | |
| ===Dangerous interactions===
| |
| {{DangerousInteractions/Intro}}
| |
| | |
| *'''[[UncertainInteraction::5-MeO-xxT]]''' - The 5-MeO class of tryptamines can be unpredictable in their interactions
| |
| *'''[[UncertainInteraction::Cannabis]]''' - Cannabis has an unexpectedly strong and somewhat unpredictable synergy with psychedelics.
| |
| *'''[[UncertainInteraction::Amphetamines]]''' - The focus and anxiety caused by stimulants is magnified by psychedelics and results in an increased risk of thought loops
| |
| *'''[[UncertainInteraction::Cocaine]]''' - The focus and anxiety caused by stimulants is magnified by psychedelics and results in an increased risk of thought loops
| |
| *'''[[UncertainInteraction::MAOIs]]'''
| |
| *'''[[UnsafeInteraction::Tramadol]]''' - This combination can cause seizures due to the lowering of the threshold by Tramadol and the potential of Mescaline to cause seziures.
| |
| *'''[[DangerousInteraction::ΑMT]]'''
| |
| | |
| ==Legal status==
| |
| {{see also|Psychedelic cacti#Legal status}}
| |
| | |
| Internationally, mescaline is classified as a Schedule I controlled substance under the United Nations 1971 Convention on Psychotropic Substances, meaning that international trade in mescaline is supposed to be closely monitored and its use is supposed to be restricted to scientific research and medical use. Natural materials containing mescaline, including peyote, are not regulated under the 1971 Psychotropic Convention.<ref name="Convention1971">{{cite web|url=https://www.unodc.org/pdf/convention_1971_en.pdf|title=Convention On Psychotropic Substances, 1971|oclc=977159148|publisher=United Nations Office on Drugs and Crime|access-date=January 3, 2020}}</ref>
| |
| | |
| *'''Australia''': Mescaline is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard.<ref name="Poisons Standard">{{cite web |url= https://www.comlaw.gov.au/Details/F2015L01534 |title=Poisons Standard October 2015 |work=Federal Register of Legislation }}</ref> A Schedule 9 substance is a substance which may be abused or misused and the manufacture, possession, sale or use of is prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.<ref name="Poisons Standard" />Peyote cacti and other mescaline-containing plants, such as San Pedro, are illegal in Western Australia, Queensland, and the Northern Territory. In other states such as Victoria and New South Wales, they are legal for ornamental and gardening purposes.{{citation needed}}
| |
| *'''Brazil''': Possession, production and sale is illegal as it is listed on Portaria SVS/MS nº 344.<ref>{{cite web|title=RESOLUÇÃO DA DIRETORIA COLEGIADA - RDC N° 130, DE 2 DE DEZEMBRO DE 2016|publication-date=December 5, 2016|language=pt|access-date=January 8, 2020|publisher=Agência Nacional de Vigilância Sanitária (Anvisa) [National Sanitary Surveillance Agency]|url=http://portal.anvisa.gov.br/documents/10181/3115436/%281%29RDC_130_2016_.pdf/fc7ea407-3ff5-4fc1-bcfe-2f37504d28b7}}</ref>
| |
| *'''Canada''': Mescaline is classified as a Schedule III drug under the Controlled Drugs and Substances Act. Peyote is listed as an exemption.<ref>{{cite web|url=https://laws-lois.justice.gc.ca/eng/acts/C-38.8/page-15.html|title=Schedule III|work=Controlled Drugs and Substances Act (S.C. 1996, c. 19)|publisher=Government of Canada|access-date=January 1, 2020}}</ref> Other mescaline containing plants are presumably illegal to possess outside of ornamental and gardening purposes.
| |
| *'''Germany''': Mescaline is controlled under Anlage I BtMG<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/anlage_i.html|title=Gesetz über den Verkehr mit Betäubungsmitteln: Anlage I|publisher=Bundesamt für Justiz [Federal Office of Justice]|access-date=December 10, 2019|language=de}}</ref> (''Narcotics Act, Schedule I''), former: Opiumgesetz (''Opium Act'') as of February 25, 1967.<ref>{{cite web|url=http://www.bgbl.de/xaver/bgbl/start.xav?startbk=Bundesanzeiger_BGBl&jumpTo=bgbl167s0197.pdf|title=Vierte Verordnung über die den Betäubungsmitteln gleichgestellten Stoffe|publisher=Bundesanzeiger Verlag|work=Bundesgesetzblatt Teil I: 1967 Nr. 10|publication-date=February 24, 1967|language=de|issn=0341-1095|oclc=924790029|page=197|}}</ref> It is illegal to manufacture, possess, import, export, buy, sell, procure or dispense it without a license.<ref>{{cite web|url=https://www.gesetze-im-internet.de/btmg_1981/__29.html|title=Gesetz über den Verkehr mit Betäubungsmitteln: § 29|publisher=Bundesamt für Justiz [Federal Office of Justice]|access-date=December 10, 2019|language=de}}</ref>
| |
| *'''The Netherlands''': Mescaline in its raw form and dried mescaline-containing cacti are considered an illegal drug. However, anyone may grow and use peyote without restriction as it is specifically exempt from legislation.{{citation needed}}
| |
| *'''Switzerland''': Mescaline is a controlled substance specifically named under Verzeichnis D.<ref>{{cite web|url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html|title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien|publisher=Bundeskanzlei [Federal Chancellery of Switzerland]|access-date=January 1, 2020|language=de}}</ref>
| |
| *'''United Kingdom''': Mescaline in purified powder form is a Class A drug. However, dried cactus can be bought and sold legally.<ref>{{cite magazine|url=http://www.erowid.org/plants/cacti/cacti_law2.shtml|title=2007 U.K. Trichocereus Cacti Legal Case|author=Regina v. Saul Sette|publisher=Erowid|date=June 2007|access-date=September 30, 2020|work=Erowid Extracts|volume=12}}</ref>
| |
| *'''United States''': Mescaline was made illegal in 1970 by the Comprehensive Drug Abuse Prevention and Control Act.<ref>{{cite web|url=http://www.deadiversion.usdoj.gov/schedules/index.html|title=Controlled Substance Schedules|access-date=September 30, 2020|publisher=Diversion Control Devision}}</ref> The drug is categorized as a Schedule I hallucinogen by the CSA. Mescaline is legal only for certain religious groups (such as the Native American Church) and in scientific and medical research. While mescaline containing cacti of the genus Echinopsis are technically controlled substances under the Controlled Substances Act, they are commonly sold publicly as ornamental plants.{{citation needed}}
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| ==See also==
| |
| | |
| *[[Responsible use]]
| |
| *[[Entheogens]]
| |
| *[[Psychedelics]]
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| *[[Phenethylamine]]
| |
| *[[Escaline]]
| |
| *[[2C-x]]
| |
| | |
| ==External links==
| |
| | |
| *[http://en.wikipedia.org/wiki/Mescaline Mescaline (Wikipedia)]
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| *[https://www.erowid.org/chemicals/mescaline/mescaline.shtml Mescaline (Erowid Vault)]
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| *[https://isomerdesign.com/PiHKAL/read.php?domain=pk&id=96 Mescaline (PiHKAL / Isomer Design)]
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| ==References==
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| {{reflist|2}}
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| {{#set:Featured=true}}
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| [[Category:Alkaloid]]
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| [[Category:Phenethylamine]]
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| [[Category:Psychedelic]]
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| [[Category:Entheogen]]
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M
MESCALINE; 3,4,5-TRIMETHOXYPHENETHYLAMINE
SYNTHESIS
A solution of 20 g 3,4,5-trimethoxybenzaldehyde, 40 mL nitromethane, and 20 mL cyclohexylamine in 200 mL of acetic acid was heated on the steam bath for 1 h. The reaction mixture was then diluted slowly and with good stirring, with 400 mL H2O, which allowed the formation of a heavy yellow crystalline mass. This was removed by filtration, washed with H2O, and sucked as dry as possible. Recrystallization from boiling MeOH (15 mL/g) yielded, after filtration and air drying, beta-nitro-3,4,5-trimethoxystyrene as bright yellow crystals weighing 18.5 g. An alternate synthesis was effective, using an excess of nitromethane as solvent as well as reagent, if the amount of ammonium acetate catalysis was kept small. A solution of 20 g 3,4,5-trimethoxybenzaldehyde in 40 mL nitromethane containing 1 g anhydrous ammonium acetate was heated on the steam bath for 4 h. The solvent was stripped under vacuum and the residual yellow oil was dissolved in two volumes of hot MeOH, decanted from some insolubles, and allowed to cool. The crystals formed are removed by filtration, washed with MeOH and air dried yielding 14.2 g. of bright yellow crystals of beta-nitro-3,4,5-trimethoxystyrene. The use of these proportions but with 3.5 g ammonium acetate gave extensive side-reaction products even when worked up after only 1.5 h heating. The yield of nitrostyrene was, in this latter case, unsatisfactory.
To a gently refluxing suspension of 2 g LAH in 200 mL Et2O, there was added 2.4 g beta-nitro-3,4,5-trimethoxystyrene as a saturated Et2O solution by use of a Soxhlet extraction condenser modified to allow the continuous return of condensed solvent through the thimble. After the addition was complete, the refluxing conditions were maintained for another 48 h. After cooling the reaction mixture, a total of 150 mL of 1.5 N H2SO4 was cautiously added, destroying the excess hydride and untimately providing two clear phases. These were separated, and the aqueous phase was washed once with 50 mL Et2O. There was then added 50 g potassium sodium tartrate, followed by sufficient NaOH to bring the pH >9. This was then extracted with 3x75 mL CH2Cl2, and the solvent from the pooled extracts was removed under vacuum. The residue was distilled at 120-130 °C at 0.3 mm/Hg giving a white oil that was dissolved in 10 mL IPA and neutralized with concentrated HCl. The white crystals that formed were diluted with 25 mL Et2O, removed by filtration, and air dried to provide 2.1 g 3,4,5-trimethoxyphenethylamine hydrochloride (M) as glistening white crystals. The sulfate salt formed spectacular crystals from water, but had a broad and uncharacteristic mp. An alternate synthesis can employ 3,4,5-trimethoxyphenylacetonitrile, as described under beta-D.
DOSAGE
200-400 mg (as the sulfate salt), 178-356 mg (as the hydrochloride salt) [Erowid Note: The original text read "178-256" but this was an error. The error was found by Bo and verified with Shulgin. See the Erowid Mescaline Dosage page for a more complete discussion of the forms of mescaline].
DURATION
10-12 h
(with 300 mg) I would have liked to, and was expecting to, have an exciting visual day, but I seemed to be unable to escape self-analysis. At the peak of the experience I was quite intoxicated and hyper with energy, so that it was not hard to move around. I was quite restless. But I spent most of the day in considerable agony, attempting to break through without success. I learned a great deal about myself and my inner workings. Everything almost was, but in the final analysis, wasn't. I began to become aware of a point, a brilliant white light, that seemed to be where God was entering, and it was inconceivably wonderful to perceive it and to be close to it. One wished for it to approach with all one's heart. I could see that people would sit and meditate for hours on end just in the hope that this little bit of light would contact them. I begged for it to continue and come closer but it did not. It faded away not to return in that particular guise the rest of the day. Listening to Mozart's Requiem, there were magnificent heights of beauty and glory. The world was so far away from God, and nothing was more important than getting back in touch with Him. But I saw how we created the nuclear fiasco to threaten the existence of the planet, as if it would be only through the threat of complete annihilation that people might wake up and begin to become concerned about each other. And so also with the famines in Africa. Many similar scenes of joy and despair kept me in balance. I ended up the experience in a very peaceful space, feeling that though I had been through a lot, I had accomplished a great deal. I felt wonderful, free, and clear.
(with 350 mg) Once I got through the nausea stage, I ventured out-of-doors and I was aware of an intensification of color and a considerable change in the texture of the cloth of my skirt and in the concrete of the sidewalk, and in the flowers and leaves that were handed me by an observer. I experienced the desire to laugh hysterically at what I could only describe as the completely ridiculous state of the entire world. Although I was afraid of motion, I was persuaded to take a ride in a car. The driver turned on the radio and suddenly the music 'The March of the Siamese Children' from 'The King and I' became the most perfect background music for the parody of real life which was indeed the normal activity of Telegraph Avenue on any Saturday morning. The perfectly ordinary people on their perfectly ordinary errands were clearly the most cleverly contrived set of characters all performing all manners of eccentric activities for our particular hilarity and enjoyment. I felt that I was at the same time both observing and performing in an outrageous moving picture. I experienced one moment of transcendant happiness when, while passing Epworth Hall, I looked out of the window of the car and up at the building and I was suddenly in Italy looking up at a gay apartment building with its shutters flung open in sunshine, and with its window boxes with flowers. We stopped at a spot overlooking the bay, but I found the view uninteresting and the sun uncomfortable. I sat there on the seat of the car looking down at the ground, and the earth became a mosaic of beautiful stones which had been placed in an intricate design which soon all began to move in a serpentine manner. Then I became aware that I was looking at the skin of a beautiful snake--all the ground around me was this same huge creature and we were all standing on the back of this gigantic and beautiful reptile. The experience was very pleasing and I felt no revulsion. Just then, another automobile stopped to look at the view and I experienced my first real feeling of persecution and I wanted very much to leave.
(with 400 mg) During the initial phase of the intoxication (between 2 and 3 hours) everything seemed to have a humorous interpretation. People's faces are in caricature, small cars seem to be chasing big cars, and all cars coming towards me seem to have faces. This one is a duchess moving in regal pomp, that one is a wizened old man running away from someone. A remarkable effect of this drug is the extreme empathy felt for all small things; a stone, a flower, an insect. I believe that it would be impossible to harm anything--to commit an overt harmful or painful act on anyone or anything is beyond one's capabilities. One cannot pluck a flower--and even to walk upon a gravel path requires one to pick his footing carefully, to avoid hurting or disturbing the stones. I found the color perception to be the most striking aspect of the experience. The slightest difference of shade could be amplified to extreme contrast. Many subtle hues became phosphorescent in intensity. Saturated colors were often unchanged, but they were surrounded by cascades of new colors tumbling over the edges.
(with 400 mg) It took a long time to come on and I was afraid that I had done it wrong but my concerns were soon ended. The world soon became transformed where objects glowed as if from an inner illumination and my body sprang to life. The sense of my body, being alive in my muscles and sinews, filled me with enormous joy. I watched Ermina fill to brimming with animal spirit, her features tranformed, her body cat-like in her graceful natural movement. I was stopped in my tracks. The world seemed to hold its breath as the cat changed again into the Goddess. As she shed her clothes, she shed her ego and when the dance began, Ermina was no more. There was only the dance without the slightest self-consconciousness. How can anything so beautiful be chained and changed by other's expectations? I became aware of myself in her and as we looked deeply into one another my boundaries disappeared and I became her looking at me.
EXTENSIONS AND COMMENTARY
Mescaline is one of the oldest psychedelics known to man. It is the major active component of the small dumpling cactus known as Peyote. It grows wild in the Southwestern United States and in Northern Mexico, and has been used as an intimate component of a number of religious traditions amongst the native Indians of these areas. The cactus has the botanical name of Lophophora williamsii or Anhalonium lewinii and is immediately recognizable by its small round shape and the appearance of tufts of soft fuzz in place of the more conventional spines. The dried plant material has been classically used with anywhere from a few to a couple of dozen of the hard tops, called buttons, being consumed in the course of a ceremony.
Throughout the more recently published record of clinical human studies with mescaline, it has been used in the form of the synthetic material, and has usually been administered as the sulfate salt. Although this form has a miserable melting point (it contains water of crystallization, and the exact melting point depends on the rate of heating of the sample) it nonetheless forms magnificent crystals from water. Long, glistening needles that are, in a sense, its signature and its mark of purity. The dosages associated with the above "qualitative comments" are given as if measured as the sulfate, although the actual form used was usually the hydrochloride salt. The conversion factor is given under "dosage" above.
Mescaline has always been the central standard against which all other compounds are viewed. Even the United States Chemical Warfare group, in their human studies of a number of substituted phenethylamines, used mescaline as the reference material for both quantitative and qualitative comparisons. The Edgewood Arsenal code number for it was EA-1306. All psychedelics are given properties that are something like "twice the potency of mescaline" or "twice as long-lived as mescaline." This simple drug is truly the central prototype against which everything else is measured. The earliest studies with the "psychotomimetic amphetamines" had quantitative psychological numbers attached that read as "mescaline units." Mescaline was cast in concrete as being active at the 3.75 mg/kg level. That means for a 80 kilogram person (a 170 pound person) a dose of 300 milligrams. If a new compound proved to be active at 30 milligrams, there was a M.U. level of 10 put into the published literature. The behavioral biologists were happy, because now they had numbers to represent psychological properties. But in truth, none of this represented the magic of this material, the nature of the experience itself. That is why, in this Book II, there is only one line given to "dosage," but a full page given to "qualitative comments".
Four simple N-modified mescaline analogues are of interest in that they are natural and have been explored in man.
The N-acetyl analogue has been found in the peyote plant, and it is also a major metabolite of mescaline in man. It is made by the gentle reaction of mescaline with acetic anhydride (a bit too much heat, and the product N-acetyl mescaline will cyclize to a dihydroisoquinoline, itself a fine white crystalline solid, mp 160-161 °C) and can be recrystallized from boiling toluene. A number of human trials with this amide at levels in the 300 to 750 milligrams range have shown it to be with very little activity. At the highest levels there have been suggestions of drowsiness. Certainly there were none of the classic mescaline psychedelic effects.
If free base mescaline is brought into reaction with ethyl formate (to produce the amide, N-formylmescaline) and subsequently reduced (with lithium aluminum hydride) it is converted to the N-methyl homologue. This base has also been found as a trace component in the Peyote cactus. And the effects of N-methylation of other psychedelic drugs have been commented upon elsewhere in these recipes, all with consistently negative results (with the noteworthy exception of the conversion of MDA to MDMA). Here, too, there is no obvious activity in man, although the levels assayed were only up to 25 milligrams.
N,N-Dimethylmescaline has been given the trivial name of Trichocerine as it has been found as a natural product in several cacti of the Trichocereus Genus but, interestingly, never in any Peyote variant. It also has proven inactive in man in dosages in excess of 500 milligrams, administered parenterally. This observation, the absence of activity of a simple tertiary amine, has been exploited in the development of several iodinated radiopharmaceuticals that are mentioned elsewhere in this book.
The fourth modification is the compound with the nitrogen atom oxidatively removed from the scene. This is the mescaline metabolite, 3,4,5-trimethoxyphenylacetic acid, or TMPEA. Human dosages up to 750 milligrams orally failed to produce either physiological or psychological changes.
One additional manipulation with some of these structures has been made and should be mentioned. These are the analogues with an oxygen atom inserted between the aromatic ring and the aliphatic chain. They are, in essence, aminoethyl phenyl ethers. The first is related to mescaline itself, 2-(3,4,5-trimethoxyphenoxy)ethylamine. Human trials were conducted over the dose range of 10 to 300 milligrams and there were no effects observed. The second is related to trichocerine, N,N-dimethyl-2-(3,4,5-trimethoxyphenoxy)ethylamine. It was inactive in man over the range of 10 to 400 milligrams. Mescaline, at a dose of 420 milligrams, served as the control in these studies.
