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Naturally occurring psychedelic compound

Pharmaceutical compound
Mescaline
Clinical data
Other namesM; Mescalin; Mezcalin; Mezcaline; Meskalin; Mezkalin; 3,4,5-Trimethoxyphenethylamine; 3,4,5-TMPEA; TMPEA; O,O-Dimethyl-5-methoxydopamine; 2C-TMA; EA-1306; NSC-30419; JOUR-5700; JOUR5700; BMND04; BMND06; BMND09
AHFS/Drugs.commescaline
Routes of
administration		Oral, smoking, insufflation, intravenous[1]
Drug classSerotonin receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
  • AU: S9 (Prohibited substance)
  • BR: Class F2 (Prohibited psychotropics)[3]
  • CA: Schedule III , except peyote
  • DE: Anlage I (Authorized scientific use only)
  • UK: Class A (Plants containing mescaline legal)
  • US: Schedule I (with religious use exceptions)
  • UN: P I (psychoactive cactus like peyote or san pedro uncontrolled)
Pharmacokinetic data
BioavailabilityUnknown (but ≥53%)[4][5]
Protein bindingUnknown (but appears minimal)[5][6][7]
MetabolismOxidative deamination, N-acetylation, O-demethylation, conjugation, other pathways[8][9]
Metabolites• 3,4,5-Trimethoxyphenyl-acetaldehyde[8][1]
• 3,4,5-Trimethoxyphenylacetic acid[1]
• 3,4,5-Trimethoxyphenylethanol[9]
• Others[8][9]
Onset of actionOral: 0.5–0.9 hours (range 0.1–2.7 hours)[10][11][1]
IVTooltip Intravenous injection: <10 minutes[12][14]
Elimination half-life3.6 hours (range 2.6–5.3 hours)[10][15][11][4]
Duration of action6.4–14 hours (range 3.0–22 hours)[10][1][11]
ExcretionUrine (≥92%; 28–60% unchanged, ≥27–31% as TMPAA, 5% as N-Ac-3,4-DiMeO-5-OH-PEA, <0.1% as NAMTooltip N-acetylmescaline)[1][4][12][8][9][16]
Identifiers
  • 2-(3,4,5-trimethoxyphenyl)ethanamine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.000.174 Edit this at Wikidata
Chemical and physical data
FormulaC11H17NO3
Molar mass211.261 g·mol−1
3D model (JSmol)
Density1.067 g/cm3
Melting point35 to 36 °C (95 to 97 °F)
Boiling point180 °C (356 °F) at 12 mmHg
Solubility in watermoderately soluble in water mg/mL (20 °C)
  • O(c1cc(cc(OC)c1OC)CCN)C
  • InChI=1S/C11H17NO3/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3 checkY
  • Key:RHCSKNNOAZULRK-UHFFFAOYSA-N checkY
  (verify)

Mescaline, also known in chemical terms as 3,4,5-trimethoxyphenethylamine, is a naturally occurring psychedelic drug and alkaloid of the phenethylamine and scaline families found in certain cacti like peyote (Lophophora williamsii) and the San Pedro cactus (Echinopsis pachanoi, others).[8][1][9][10]

The drug is used recreationally, spiritually, and medically, with psychedelic effects occurring at doses of 100 to 1,000 mg orally[10][17] and it can be used in pure form or in the form of mescaline-containing cacti.[8][18][9] Mescaline induces a psychedelic experience characterized by visual changes, altered perception of time, space, and self, synesthesia, and spiritual experiences, with an onset of 30 to 60 minutes, a time to peak of 2 to 4 hours, and a duration that increases with dose and ranges from 6 to 14 hours.[1][10][11]

Mescaline primarily acts as a partial agonist at serotonin 5-HT2A receptors, with varying affinity and efficacy across multiple other receptors and targets.[10][1] The serotonin 5-HT2A receptor antagonist ketanserin blocks mescaline's psychoactive effects.[11] Mescaline is a relatively hydrophilic compound structurally related to dopamine,[20][9] first synthesized in 1919,[21] with numerous synthetic methods[22] and potent analogues developed since.[20][23] It occurs naturally in various cacti species, with concentrations varying widely, and is biosynthesized in plants from amino acids like phenylalanine and tyrosine.[8][24][22]

The practice of humans consuming mescaline-containing cacti dates back over 6,000 years.[8][21] Peyote cacti were studied scientifically in the 1800s, culminating in the isolation of mescaline as the active psychedelic constituent in cacti, legal recognition of religious use, and ongoing exploration of the therapeutic potential of mescaline and other analogues.[21] Mescaline was the first psychedelic compound to be characterized by the Western world and has been referred to as the "first psychedelic".[21][25]

Mescaline and the cacti that produce it are largely illegal worldwide, though exceptions exist for religious, scientific, or ornamental use, and the compound has influenced many notable cultural figures, for instance Aldous Huxley and Alexander Shulgin among others.[21][26][20] Very few studies of mescaline in people have been conducted since the early 1970s.[21][27] However, the drug is now being studied in terms of its effects and for potential medical use once again as of the early 2020s.[10][27][28]

Use and effects

[edit]

Mescaline is used recreationally, spiritually, and medically.[8][1] It is typically taken orally. The drug is used as a psychedelic at doses of 100 to 1,000 mg orally.[10][17][29][22] Low doses are 100 to 200 mg, an intermediate or "good effect" dose is 500 mg, and a high (ego-dissolution) dose is 1,000 mg.[10][17] In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin listed a dose range of 200 to 400 mg as the sulfate salt and 178 to 356 mg as the hydrochloride salt.[20][30] Microdosing involves the use of daily mescaline doses of less than 75 mg.[10][17 In addition to pure form, mescaline is used in the form of such as and the . Doses when mescaline is used in the form of fresh or dried cacti have also been described.[31][32][18]

In traditional peyote preparations, the top of the cactus is cut off, leaving the large tap root along with a ring of green photosynthesizing area to grow new heads. These heads are then dried to make disc-shaped buttons. Buttons are chewed to produce the effects or soaked in water to drink. However, the taste of the cactus is bitter, so modern users will often grind it into a powder and pour it into capsules to avoid having to taste it. The average 76 mm (3.0 in) peyote button contains about 25 mg mescaline.[33] Some analyses of traditional preparations of San Pedro cactus have found doses ranging from 34 mg to 159 mg of total alkaloids, a relatively low and barely psychoactive amount. It appears that patients who receive traditional treatments with San Pedro ingest sub-psychoactive doses and do not experience psychedelic effects.[34]

The onset of the effects of mescaline given orally is 0.5 to 0.9 hours on average with a range of 0.1 to 2.7 hours.[10][11][1] Its effects peak after 1.9 to 4.0 hours with a range of 0.5 to 8.0 hours.[10][35][15][11] The duration of mescaline appears to be dose-dependent, varying from 6.4 hours on average (range 3.0–10 hours) at a dose of 100 mg, 9.7 to 11 hours on average (range 5.6–22 hours) at moderate doses of 300 to 500 mg, and 14 hours on average (range 7.2–22 hours) at a dose of 800 mg.[10][11] Cases of mescaline having unusually prolonged or delayed effects have also been described.[36]

Mescaline induces a psychedelic state comparable to those produced by LSD and psilocybin, but with unique characteristics.[27] Subjective effects may include altered thinking processes, an altered sense of time and self-awareness, and closed- and open-eye visual phenomena.[37] In PiHKAL, Shulgin described the effects of mescaline based on a collection of experience reports.[20] The effects included brightened colors, increased visual contrast, open-eye visuals like colors and patterns, pareidolia, increased significance of objects, enhanced music appreciation, feeling intoxicated, self-analysis, insights, increased body awareness, feelings of joy, happiness, and peacefulness, feeling hyper and energized, feelings of empathy, things feeling ridiculous, humor and laughter, religious feelings, restlessness, social discomfort and avoidance, and nausea, among others.[20] Mescaline was one of Shulgin's "magical half-dozen" psychedelic drugs in PiHKAL.[20]

Prominence of color with mescaline is distinctive, appearing brilliant and intense.[8] Recurring visual patterns observed during the mescaline experience include stripes, checkerboards, angular spikes, multicolor dots, and very simple fractals that can turn very complex.[38] The English writer Aldous Huxley described these self-transforming amorphous shapes as like animated stained glass illuminated from light coming through the eyelids in his autobiographical book The Doors of Perception (1954).[26] Like LSD, mescaline induces distortions of form and kaleidoscopic experiences but they manifest more clearly with eyes closed and under low lighting conditions.[38] Heinrich Klüver coined the term "cobweb figure" in the 1920s to describe one of the four form constant geometric visual hallucinations experienced in the early stage of a mescaline trip: "Colored threads running together in a revolving center, the whole similar to a cobweb".[39] The other three are the chessboard design, tunnel, and spiral.[39] Klüver wrote that "many 'atypical' visions are upon close inspection nothing but variations of these form-constants."[39] An unusual but unique characteristic of mescaline use is the "geometrization" of three-dimensional objects.[38][40] The object can appear flattened and distorted, similar to the presentation of a Cubist painting.[38][40] Detailed descriptions of the psychedelic experience induced by mescaline have been given by many authors.[22][41][42][43][44][26][20]

The subjective effects of mescaline are qualitatively similar to those of LSD and psilocybin.[10][45][15][12] Based on anecdotal evidence however, mescaline is said to be less threatening and to produce less ego dissolution than other psychedelics like LSD.[27][25] This may in part be due its slow onset allowing for a more comfortable ease-in of effects.[27] In addition, mescaline is typically dosed at lower doses than LSD or psilocybin in terms of doses with equivalent or comparable strength.[11][15][10] According to a study in the Netherlands, ceremonial San Pedro use seems to be characterized by relatively strong spiritual experiences, and low incidence of challenging experiences.[46] Mescaline, LSD, and psilocybin appear to produce similar color enhancement in clinical studies, though more research is needed.[48][49][50]

Contraindications

[edit]

Contraindications of psychedelic drugs like mescaline include severe cardiovascular disease, epilepsy or seizures, schizophrenia and other psychotic disorders, bipolar disorder, and pregnancy, among others.[51][52] Serotonin 5-HT2A receptor antagonists such as atypical antipsychotics and certain antidepressants may block psilocybin's hallucinogenic effects and hence may be considered contraindicated in this sense.[53][54]

[edit]

Side effects of mescaline include fatigue, weakness, impaired concentration, restlessness, tension, anxiety, panic, and social discomfort and avoidance, headache, pupil dilation, nausea, vomiting, sweating, trembling, discomfort, feeling hot or cold, palpitations, chest and neck pains, shortness of breath, increased heart rate and blood pressure, and increased body temperature, among others.[20][1][10][55] Nausea and vomiting are important dose-limiting side effects of mescaline and occur at greater rates than with other psychedelics like LSD and psilocybin.[55][11][15] High doses of mescaline, such as 800 mg and above, are not well-tolerated due to substantial nausea and vomiting.[45][11][55] On the other hand, mescaline appears to induce less fear and anxiety than LSD and psilocybin even at equivalent doses.[10][45][55] Rarely, in susceptible individuals such as people with a family history of schizophrenia, mescaline may cause psychosis.

Tolerance

[edit]

Mescaline is associated with rapid tolerance development, including cross-tolerance with other psychedelics like LSD and psilocybin.[18][1] This tolerance is apparent within a few days and resets after 3 or 4 days of abstinence.[1][18]

Overdose

[edit]

Only a single case of death due to mescaline, as peyote, has been described, and was likely due to asphyxiation by vomit rather than overdose or toxicity.[57][58][6][59][22] In terms of extrapolated human lethal dose based on animal studies, the lethal dose of mescaline relative to a typical recreational dose has been estimated to be 24-fold or around 8,400 mg.[57][58][59] However, mescaline has reportedly been taken by humans at doses of up to 8,000 mg without apparent toxic reactions.[18][22][60][61] On the other hand, there is one unverified reported case of death due to 15,000 mg intravenously, which would equate to about 150 to 200 mg/kg.[22] The median lethal dose (LD50) of mescaline has been determined in various animal species, with the values including 212 to 315 mg/kg i.p. in mice, 132 to 410 mg/kg i.p. in rats, 328 mg/kg i.p. in guinea pigs, 54 mg/kg in dogs, and 130 mg/kg i.v. in rhesus macaques, among others.[22][12][62] It has been said that it would be difficult to take enough mescaline to cause death in humans.[22] No deaths due to peyote use have been reported aside from the asphyxiation case.[63][22][59] The highest known dose of peyote taken is 90 dried buttons.[64][22][65]

Interactions

[edit]

The serotonin 5-HT2A receptor antagonist ketanserin has been found to block the psychoactive effects of mescaline.[11][66] Similarly, the antipsychotic chlorpromazine, which acts as both a dopamine D2 receptor antagonist and to a lesser extent as a serotonin 5-HT2A receptor antagonist, has been reported to reverse the psychoactive effects of mescaline.[67][68][69] Other phenothiazines, such as promethazine and diethazine, have also been reported to antagonize the effects of mescaline in humans, whereas prochlorperazine was much less effective and promazine was ineffective.[12][14] Barbiturates, which are GABAA receptor positive allosteric modulators, have been found to abolish the anxiety induced by mescaline.[12]

It is unclear whether mescaline is metabolized by monoamine oxidase (MAO) enzymes[70] or whether monoamine oxidase inhibitors (MAOIs) might increase the effects of mescaline.[70][71] No clinical studies of mescaline in combination with MAOIs are known to have been published.[70] However, there are preliminary reports that harmala alkaloids, which are reversible inhibitors of monoamine oxidase A (RIMAs), may potentiate the effects of mescaline in humans, and the combination of mescaline or mescaline-containing cacti with harmala alkaloids has been referred to as "peyohuasca".[71][22][70] In accordance with these findings, the harmala alkaloid and RIMA harmine has been reported to augment the effects of mescaline in animals.[22] On the other hand, Daniel Trachsel has stated that mescaline is not metabolized by MAO, instead being metabolized by semicarbazide-sensitive amine oxidase (SSAO), and hence that MAOIs that do not also inhibit SSAO should have no effect on the metabolism of mescaline.[23] Accordingly, the MAOI iproniazid did not potentiate the behavioral effects of mescaline in rats.[23][12][72]

Pharmacology

[edit]

Pharmacodynamics

[edit]
Mescaline activities
TargetAffinity (Ki, nM)
5-HT1A1,841–4,600
5-HT1B>10,000
5-HT1D>10,000
5-HT1E5,205
5-HT1FND
5-HT2A550–17,400 (Ki)
88–30,200 (EC50Tooltip half-maximal effective concentration)
33–107% (EmaxTooltip maximal efficacy)
5-HT2B793–800 (Ki)
1,100–>20,000 (EC50)
91% (Emax)
5-HT2C300–17,000 (Ki)
20–19,500 (EC50)
22–109% (Emax)
5-HT3>10,000
5-HT4ND
5-HT5A>10,000
5-HT6>10,000
5-HT7>10,000
α1A>15,000
α1B>10,000
α1DND
α2A1,400–8,930
α2B>10,000
α2C745
β1–β2>10,000
D1>10,000
D2>10,000
D3>17,000
D4>10,000
D5>10,000
H1–H4>10,000
M1–M5>10,000
TAAR13,300 (Ki) (rat)
11,000 (Ki) (mouse)
3,700–4,800 (EC50) (rodent)
>10,000 (EC50) (human)
I12,678
σ1–σ2>10,000
SERTTooltip Serotonin transporter>30,000 (Ki)
367,000 (IC50Tooltip half-maximal inhibitory concentration)
NETTooltip Norepinephrine transporter>30,000 (Ki)
>900,000 (IC50)
DATTooltip Dopamine transporter>30,000 (Ki)
841,000 (IC50)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [73][74][10][1]
[75][76][77][78][79][80][81]

Mescaline acts as an agonist of the serotonin 5-HT2A receptor to produce its psychedelic effects.[82][83][84][11] Its EC50Tooltip half-maximal effective concentration at the serotonin 5-HT2A receptor is approximately 10,000 nM and at the serotonin 5-HT2B receptor is greater than 20,000 nM.[1] How activating the 5-HT2A receptor leads to psychedelic effects is still unknown, but it is likely that somehow it involves excitation of neurons in the prefrontal cortex.[85] In addition to the serotonin 5-HT2A and 5-HT2B receptors, mescaline is also known to bind to the serotonin 5-HT2C receptor and a number of other targets.[1][77][75] The drug shows pronounced biased agonism at the serotonin 5-HT2C receptor.

Mescaline lacks affinity for the monoamine transporters, including the serotonin transporter (SERT), norepinephrine transporter (NET), and dopamine transporter (DAT) (Ki > 30,000 nM).[1] However, it has been found to increase levels of the major serotonin metabolite 5-hydroxyindoleacetic acid (5-HIAA) at high doses in rodents.[1][9][87] This finding suggests that mescaline might inhibit the reuptake and/or induce the release of serotonin at such doses.[1][9][88] In any case, this possibility has not yet been further assessed or demonstrated.[1] Besides serotonin, mescaline might also weakly induce the release of dopamine, but this is probably of modest significance, if it occurs.[9][89] In accordance, there is no evidence of the drug showing addiction or dependence.[9] Mescaline appears to be inactive in terms of norepinephrine release induction and indirect sympathomimetic activity.[90] Other psychedelic phenethylamines, including the closely related 2C, DOx, and TMA drugs, are inactive as monoamine releasing agents and reuptake inhibitors.[91][92] However, an exception is trimethoxyamphetamine (TMA), the amphetamine analogue of mescaline, which is a very low-potency serotonin releasing agent (EC50Tooltip half-maximal effective concentration = 16,000 nM).[91] The possible monoamine-releasing effects of mescaline would likely be related to the compound's phenethylamine backbone[9]

Mescaline is a relatively low-potency psychedelic, with active doses in the hundreds of milligrams and micromolar affinities for the serotonin 5-HT2A receptor.[8][1] For comparison, psilocybin is approximately 25-fold more potent (doses in the tens of milligrams) and lysergic acid diethylamide (LSD) is approximately 5,000-fold more potent (doses in the tens to hundreds of micrograms).[45][1] There have been efforts to develop more potent analogues of mescaline.[8][20][93][23][94] Difluoromescaline and trifluoromescaline are more potent than mescaline, as is its amphetamine homologue TMA.[93][23][95] Escaline and proscaline are also both more potent than mescaline, showing the importance of the 4-position substituent with regard to receptor binding.[20][23][96]

It is unclear why mescaline produces more nausea and vomiting than other psychedelics like LSD and psilocybin.[55] In any case, the serotonin 5-HT2A receptor antagonist ketanserin blocked not only the psychoactive but also the physical side effects of mescaline including nausea and vomiting, suggesting that these effects may be mediated by serotonin 5-HT2A receptor activation.[11]

There is no evidence of acute tolerance with mescaline.[4] However, tolerance to mescaline builds with repeated use, lasting for a few days.[1][18] The drug causes cross-tolerance with other psychedelics like LSD and psilocybin.[1][18]

The cryo-EM structures of the serotonin 5-HT2A receptor with mescaline, as well as with various other psychedelics and serotonin 5-HT2A receptor agonists, have been solved and published by Bryan L. Roth and colleagues.[97][98]

Pharmacokinetics

[edit]

Absorption

[edit]

Mescaline is usually taken orally, although it may also be insufflated, smoked, or given intravenously. Taken orally, it is rapidly absorbed from the gastrointestinal tract.[12] The oral bioavailability of mescaline is unknown.[5] However, since at least 53% of orally administered mescaline is excreted in urine unchanged, the bioavailability appears to be at least 53%.[4] Peak concentrations of mescaline occur after approximately 1.6 to 2.3 hours on average (range 1.0–6.0 hours).[10][15][11] However, there is a delay of 1 to 2 hours following peak levels in terms of the drug producing maximal psychoactive and behavioral effects.[23] The pharmacokinetics of mescaline are dose-proportional over an oral dose range of 100 to 800 mg.[10][11]

Distribution

[edit]

Mescaline is distributed to the liver, spleen, and kidneys at many times higher levels than blood or brain based on animal studies.[12][1] It is said that a great proportion of mescaline is combined with hepatic proteins, which is said to delay its onset and elimination half-life.[1] The exact portion bound to plasma proteins seems to be unknown, but appears to be minimal.[5][6][7]

Mescaline appears to have relatively poor blood–brain barrier permeability due to its low lipophilicity.[9][4][45] However, it is still able to cross into the central nervous system and produce psychoactive effects at sufficiently high doses.[9][4] The poor central permeability of mescaline appears to be responsible for its delayed onset of effects and is also thought to contribute to its low potency.[4][23][45][99]

Metabolism

[edit]
Metabolism of mescaline in humans and/or animals.

Mescaline given orally appears to be subject to first-pass metabolism of about 50%.[4] Following the first pass, mescaline appears to be subject to relatively limited metabolism.[4]

The primary metabolic pathway of mescaline is oxidative deamination.[70][8][1] The specific enzymes mediating the deamination of mescaline are controversial however.[70] Monoamine oxidase (MAO), diamine oxidase (DAO; histamine oxidase), semicarbazide-sensitive amine oxidase (SSAO), and/or other enzymes may be responsible.[23] Preclinical studies of mescaline given in combination with inhibitors of MAO and/or DAO, such as iproniazid, pargyline, and semicarbazide, have been conducted, but findings have been conflicting.[70][23][12][101] Mescaline has been reported to be a poor or negligible substrate of highly purified human MAO in-vitro.[12][102] Mescaline is converted via deamination into 3,4,5-trimethoxyphenylacetaldehyde (TMPA) as an intermediate and then into 3,4,5-trimethoxyphenylacetic acid (TMPAA) or 3,4,5-trimethoxyphenylethanol (TMPE).[1][9][36] β-Hydroxymescaline may also be a minor metabolite of mescaline formed by dopamine β-hydroxylase (DBH), though this remains unclear.[23][103][104]

Mescaline appears not to be subject to metabolism by CYP2D6 based on in-vitro studies with human liver microsomes.[105] Similarly, the in-vitro cytotoxicity of mescaline does not appear to be affected by cytochrome P450 (CYP450) enzyme inhibitors.[106] Conversely, it was potentiated by the MAO-A inhibitor clorgiline but not by the MAO-B inhibitor rasagiline.[106] These findings were in contrast to those with the related compound 2C-B, which was potentiated by rasagiline but not by clorgiline.[106]

Circulating peak and area-under-the-curve concentrations of mescaline and TMPAA are similar with oral administration of mescaline.[11][4] Conversely, levels of N-acetylmescaline (NAM) are far lower than those of mescaline or TMPAA and are thought not to be of clinical relevance.[11][4] Intravenous injection of mescaline may result in less hepatic deamination than with oral administration.[1][4]

It has been theorized that active metabolites of mescaline might contribute to its psychoactive effects.[9][8][23][107][108][36][72] Relatedly, TMPA and TMPE were reported in early research to show pharmacological effects in rats and rabbits with greater potency than mescaline.[36][72] In addition, co-administration of mescaline with the aldehyde dehydrogenase inhibitor (ALDHI) calcium carbimide, which elevates TMPA and/or TMPE levels, has been reported to produce extreme reactions in rabbits at doses at which mescaline alone was inactive.[36] Similarly, co-administration of TMPE with calcium carbimide markedly potentiated the effects of TMPE.[72] However, subsequent research found that TMPA, TMPE, and NAM all failed to produce mescaline-like effects in rodent drug discrimination tests, and this was the case even when they were co-administered with calcium carbimide.[8][107][109] Likewise, another subsequent study found that TMPE and TMPAA were both inactive in producing behavioral effects in rodents, while TMPA was much less potent than mescaline.[108] Another study found TMPAA to be inactive in animals as well.[36][110] As with animal findings, both TMPAA and NAM have been said to be inactive based on human tests.[20][16] It has also been noted that metabolites like TMPA and TMPE are rapidly metabolized.[108] As such, metabolites of mescaline like TMPA, TMPE, TMPAA, and NAM do not appear to be involved in the drug's psychedelic-related effects.[107][109][16]

3,4,5-Trimethoxyamphetamine (TMA), the α-methyl analogue of mescaline and an MAO-resistant psychedelic, is only about twice as potent as mescaline as a psychedelic in humans despite having similar serotonin receptor affinity.[23][107] This suggests that the deamination of mescaline has a relatively limited impact on its potency, compared to for example the 2C series of psychedelics.[107] Another analogue of mescaline, the deuterated isotopologue Alpha-D (α,α-dideuteromescaline), has been reported to be roughly one-third more potent than mescaline as a psychedelic in humans, albeit based on limited testing.[23] This is consistent with findings of about one-third of a dose of mescaline being metabolized via deamination.[23]

Elimination

[edit]

Mescaline given orally is excreted 87% in urine within 24 hours and 92% in urine within 48 hours.[1][12][111][16] During the first hour after administration, 81.4% of mescaline is excreted unchanged while 13.2% is excreted as its deaminated metabolite 3,4,5-trimethoxyphenylacetic acid (TMPAA).[1][16] However, after the first hour, the percentage excreted as unchanged mescaline declines and the percentage excreted as TMPAA rises.[1][16] Ultimately, mescaline is excreted in urine 28 to 60% unchanged, 27 to 30% or more as TMPAA, 5% as N-acetyl-3,4-dimethoxy-5-hydroxyphenylethylamine, and less than 0.1% as N-acetylmescaline.[12][16] Other minor or trace excreted metabolites have also been observed.[16] In a more modern study published in 2025, mescaline was eliminated in urine 53% as unchanged mescaline and 31% as TMPAA.[4]

Mescaline was originally reported to have an elimination half-life of 6 hours based on a study conducted in the 1960s.[1][15][16] However, subsequent research published in the 2020s found that its half-life is actually about 3.6 hours (range 2.6–5.3 hours).[10][15][11][4] The previous higher estimate is believed to have been due to small sample numbers and collective measurement of mescaline metabolites.[15] The elimination half-life of mescaline does not appear to be dose-dependent.[10][15] TMPAA has a half-life of about 3.7 to 4.1 hours, similar to that of mescaline.[4] Mescaline has a similar half-life as LSD yet has a longer duration.[10] This is due to mescaline having slower absorption and onset rather than a longer half-life.[10][15]

Chemistry

[edit]

Mescaline, also known as 3,4,5-trimethoxyphenethylamine (3,4,5-TMPEA), is a substituted phenethylamine derivative.[112][9] It is closely structurally related to the dopamine (3,4-dihydroxyphenethylamine), norepinephrine (3,4,β-trihydroxyphenethylamine), and epinephrine (3,4,β-trihydroxy-N-methylphenethylamine).[112] In contrast to the catecholamine neurotransmitters however, mescaline acts primarily on the serotonergic system rather than on the dopaminergic or adrenergic systems.[8]

Properties

[edit]
A sample of pure mescaline.

The physical properties and general chemistry of mescaline have been reviewed.[12] The compound is relatively hydrophilic with low fat solubility.[9] Its predicted log P (XLogP3) is 0.7.[112]

Synthesis

[edit]

Mescaline was first ever psychedelic drug synthesized by chemists.[21] Ernst Späth's 1919 total synthesis started from 3,4,5-trimethoxy­benzoyl chloride.[113] Several approaches using different starting materials have been developed since, including the following:[22]

Analogues

[edit]

A large number of structural analogues of mescaline that act as psychedelics have been developed.[20][23] These drugs often have far greater potency than mescaline itself.[20][23] Examples include scalines like escaline, 3Cs like 3,4,5-trimethoxyamphetamine (TMA or TMA-1; α-methylmescaline), 2Cs like 2C-B, and DOx drugs like DOM, among others.[20][23] Other notable analogues of mescaline include N-methylmescaline (found in Pachycereus pringlei), trichocereine (N,N-dimethylmescaline), mescaline-FLY, and NBOMe-mescaline, among others.[20][23] Deuterated isotopologues of mescaline include α-D (α,α-dideuteromescaline), β-D (β,β-dideuteromescaline), α,β-D (α,β-dideuteromescaline), and 4-D (4-trideuteromescaline), among others.[20][23]

Natural occurrence

[edit]
Trichocereus pachanoi (San Pedro cactus) in Peru.
Dried peyote (Lophophora williamsii), containing ~5 to 6% mescaline by weight.

Mescaline has been isolated from numerous cactus species, including Echinopsis (Trichocereus), Gymnocalycium, Lophophora, Opuntia, Stenocereus, and Turbinicarpus species, among others.[22] It occurs at the highest known concentrations in Lophophora williamsii (peyote), where it is highly variable but makes up 0.1 to 0.255% fresh weight and 0.9 to 6.3% of dry weight.[22] Levels of mescaline are much lower in other Lophophora species.[22] The compound also occurs in relatively high concentrations in various Echinopsis species, for instance Echinopsis pachanoi (San Pedro cactus), ranging from 0.02 to 0.12% fresh weight and 0.331 to 2.0% dry weight in this species.[22] Mescaline occurs in only small or trace amounts in most other cactus species in which it has been detected.[22]

Mescaline content in selected cactus species[22]
Plant source Amount of mescaline (% of dry weight)
Echinopsis lageniformis (Bolivian torch cactus, syns. Echinopsis scopulicola, Trichocereus bridgesii)[128]Average 0.56%; 0.85% in one cultivar of Echinopsis scopulicola[128][129]
Leucostele terscheckii (syns Echinopsis terscheckii, Trichocereus terscheckii)[130]0.005–2.375%[131][132]
Lophophora williamsii (peyote)[133]0.01–5.5%[134]
Trichocereus macrogonus var. macrogonus (Peruvian torch, syns Echinopsis peruviana, Trichocereus peruvianus)[129]0.01–0.05%;[131] 0.24–0.81%[129]
Trichocereus macrogonus var. pachanoi (San Pedro cactus, syns Echinopsis pachanoi, Echinopsis santaensis, Trichocereus pachanoi)[135]0.23–4.7%;[129] 0.32% under its synonym Echinopsis santaensis[129]
Trichocereus uyupampensis (syn. Echinopsis uyupampensis)0.05%[129]
Trichocereus tacaquirensis (subsp. taquimbalensis syn. Trichocereus taquimbalensis) 0.005–2.7%[136]

As shown in the accompanying table, the concentration of mescaline in different specimens can vary largely within a single species.[22] Moreover, the concentration of mescaline within a single specimen varies as well.[137]

In peyote, mescaline constitutes about 30% of total alkaloid content.[139][9][140] For comparison, the alkaloid contents of other major constituents include pellotine 17%, anhalonidine 14%, anhalamine 8%, hordenine 8%, and lophophorine 5%.[139][9][140]

It has also reported to be found in small amounts in certain members of the bean family, Fabaceae, including Senegalia berlandieri (syn. Acacia berlandieri),[141] although these reports have been challenged and have been unsupported in any additional analyses.[22][142]

In plants, mescaline may be the end-product of a pathway utilizing catecholamines as a method of stress response, similar to how animals may release such compounds and others such as cortisol when stressed. The in vivo function of catecholamines in plants has not been investigated, but they may function as antioxidants, as developmental signals, and as integral cell wall components that resist degradation from pathogens. The deactivation of catecholamines via methylation produces alkaloids such as mescaline.[143]

Biosynthesis

[edit]
Biosynthesis of mescaline.

Mescaline is biosynthesized from tyrosine, which, in turn, is derived from phenylalanine by the enzyme phenylalanine hydroxylase.[8][24][22] In Lophophora williamsii (peyote), dopamine converts into mescaline in a biosynthetic pathway involving m-O-methylation and aromatic hydroxylation.[144]

Tyrosine and phenylalanine serve as metabolic precursors towards the synthesis of mescaline. Tyrosine can either undergo a decarboxylation via tyrosine decarboxylase to generate tyramine and subsequently undergo an oxidation at carbon 3 by a monophenol hydroxylase or first be hydroxylated by tyrosine hydroxylase to form L-DOPA and decarboxylated by DOPA decarboxylase. These create dopamine, which then experiences methylation by a catechol-O-methyltransferase (COMT) by an S-adenosyl methionine (SAM)-dependent mechanism. The resulting intermediate is then oxidized again by a hydroxylase enzyme, likely monophenol hydroxylase again, at carbon 5, and methylated by COMT. The product, methylated at the two meta positions with respect to the alkyl substituent, experiences a final methylation at the 4 carbon by a guaiacol-O-methyltransferase, which also operates by a SAM-dependent mechanism. This final methylation step results in the production of mescaline.

Phenylalanine serves as a precursor by first being converted to L-tyrosine by L-amino acid hydroxylase. Once converted, it follows the same pathway as described above.[143][145]

History

[edit]
The stela of the cactus bearer, a piece of ancient Peruvian art depicting the San Pedro cactus.

Archaeological evidence from sites in the United States, Mexico, and Peru indicates that mescaline-containing cacti have been used for over 6,000 years.[8] Europeans recorded use of peyote in Native American religious ceremonies upon early contact with the Huichol people in Mexico.[146] Other mescaline-containing cacti such as the San Pedro cactus have a long history of use in South America, from Peru to Ecuador.[147][148][149][150] While religious and ceremonial peyote use was widespread in the Aztec Empire and northern Mexico at the time of the Spanish conquest, religious persecution confined it to areas near the Pacific coast and up to southwest Texas. However, by 1880, peyote use began to spread north of South-Central America with "a new kind of peyote ceremony" inaugurated by the Kiowa and Comanche people. These religious practices, incorporated legally in the United States in 1920 as the Native American Church, have since spread as far as Saskatchewan, Canada.[151]

Arthur Heffter, the chemist who isolated mescaline and discovered its effects.

Peyote was first described by Bernardino de Sahagún in 1560.[12] It was first scientifically named as Peyotl zacatensis by Francisco Hernández in 1638. Botanical studies of peyote began in the 1840s and the drug was listed in the Mexican pharmacopeia.[9] The first use of mescal buttons was published by John Raleigh Briggs in 1887.[9][139][152] However, he took a very low dose of the drug, and in the modern literature, the symptoms he experienced have been attributed to a severe panic attack in response to the drug.[153][152] In 1887, the German pharmacologist Louis Lewin received his first sample of the peyote cactus, found numerous new alkaloids and later published the first methodical analysis of it.[18] The effects of mescaline in humans were first properly described by D. W. Prentiss and Francis P. Morgan in 1895.[139][41] Mescaline was first isolated and identified in 1897 by the German chemist Arthur Heffter.[9][154] He showed that mescaline was exclusively responsible for the psychoactive or hallucinogenic effects of peyote.[9] However, other components of peyote, such as hordenine, pellotine, and anhalinine, are also active.[9] Mescaline was first synthesized in 1919 by Ernst Späth.[113]

Three major books on mescaline and/or peyote were published in the mid-to-late 1920s.[21][155] These included French pharmacist Alexandre Rouhier's Le Peyotl: La Plante Qui Fait les Yeux Émerveillés (Peyote: The Plant That Fills the Eyes with Marvels) in 1927,[21][156][153][44] the German psychiatrist Kurt Beringer's Der Meskalinrausch, seine Geschichte und Erscheinungsweise (Mescaline Intoxication, its History and Manifestation) in 1927,[21][155][42] and German–American psychologist Heinrich Klüver's Mescal: The Divine Plant and Its Psychological Effects in 1928.[21][155][43]

Studies of the potential therapeutic effects of mescaline started in the 1950s.[9] It was studied as part of psychedelic-assisted psychotherapy by Walter Frederking by 1953.[12][157][158] Aldous Huxley's book The Doors of Perception, about his experience with mescaline, was published in 1954.[159] In 1955, English politician Christopher Mayhew took part in an experiment for BBC's Panorama, in which he ingested 400 mg of mescaline under the supervision of psychiatrist Humphry Osmond.[21][160][161][162] Though the recording was deemed too controversial and ultimately omitted from the show, Mayhew praised the experience, calling it "the most interesting thing I ever did" and saying that it was "profoundly thought-provoking".[21][160][161][162]

The mechanism of action of mescaline, activation of the serotonin 5-HT2A receptors, became fully known in the 1990s.[9] A serotonin 5-HT2A receptor antagonist, specifically ketanserin, was first clearly shown to block the psychedelic effects of mescaline in humans by Matthias Liechti and colleagues in 2024.[11]

The history of mescaline was reviewed in the 2019 book Mescaline: A Global History of the First Psychedelic by cultural historian Mike Jay.[163][21]

Society and culture

[edit]

Religious use

[edit]

Mescaline-containing cacti are used as entheogens for religious purposes by certain Latin American and Native American and groups.[164][21] The Huichol (Wixárika) people of Mexico and the Native American Church use peyote, while the native people of Peru use the San Pedro cactus (huachuma).[164][21] The use of mescaline-containing cacti for such purposes by Mexican and South American people dates back thousands of years.[164][21] The use of peyote spread from the Huichol people into Native American tribes such as the Kiowa and Comanche in the late 1800s.[164][21]

Notable individuals

[edit]

Media representations

[edit]

Movies

[edit]

Documentaries

[edit]
[edit]

United States

[edit]

In the United States, mescaline was made illegal in 1970 by the Comprehensive Drug Abuse Prevention and Control Act, categorized as a Schedule I hallucinogen.[189] The drug is prohibited internationally by the 1971 Convention on Psychotropic Substances.[190] Mescaline is legal only for certain religious groups (such as the Native American Church by the American Indian Religious Freedom Act of 1978) and in scientific and medical research. In 1990, the Supreme Court ruled that the state of Oregon could ban the use of mescaline in Native American religious ceremonies. The Religious Freedom Restoration Act (RFRA) in 1993 allowed the use of peyote in religious ceremony, but in 1997, the Supreme Court ruled that the RFRA is unconstitutional when applied against states.[191] Many states, including the state of Utah, have legalized peyote usage with "sincere religious intent", or within a religious organization,[citation needed] regardless of race.[192] Synthetic mescaline, but not mescaline derived from cacti, was officially decriminalized in the state of Colorado by ballot measure Proposition 122 in November 2022.[193]

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.[194]

United Kingdom

[edit]

In the United Kingdom, mescaline in purified powder form is a Class A drug. However, dried cactus can be bought and sold legally.[195]

Australia

[edit]

Mescaline is considered a schedule 9 substance in Australia under the Poisons Standard (February 2020).[196] A schedule 9 substance is classified as "Substances with a high potential for causing harm at low exposure and which require special precautions during manufacture, handling or use. These poisons should be available only to specialised or authorised users who have the skills necessary to handle them safely. Special regulations restricting their availability, possession, storage or use may apply."[196]

Other countries

[edit]

In Canada, France, the Netherlands, and Germany, mescaline in raw form and dried mescaline-containing cacti are considered illegal drugs. However, anyone may grow and use peyote (Lophophora williamsii) as well as Echinopsis pachanoi and Echinopsis peruviana (San Pedro cactus) without restriction, as they are specifically exempt from legislation.[133] In Canada, mescaline is classified as a schedule III drug under the Controlled Drugs and Substances Act, whereas peyote is exempt.[197] In Russia, mescaline, its derivatives, and mescaline-containing plants are banned as narcotic drugs (Schedule I).[198]

Research

[edit]

Mescaline has a wide array of suggested medical usage, including treatment of depression, anxiety, PTSD,[199] nicotine dependence, and alcoholism.[200][201] However, its status as a Schedule I controlled substance in the Convention on Psychotropic Substances limits availability of the drug to researchers. Because of this, very few studies concerning mescaline's activity and potential therapeutic effects in people have been conducted since the early 1970s.[202][199][27] However, the drug is under development by Journey Colab under the code name JOUR-5700 and by Biomind Labs under the code names BMND04, BMND06, and BMND09 for various medical applications, such as treatment of alcoholism.[27][203][204][28][208]

See also

[edit]

References

[edit]
  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 Vamvakopoulou IA, Narine KA, Campbell I, Dyck JR, Nutt DJ (January 2023). "Mescaline: The forgotten psychedelic". Neuropharmacology. 222 109294. doi:10.1016/j.neuropharm.2022.109294. PMID 36252614.
  2. ↑ name="Anvisa2023"Anvisa (24 July 2023). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 25 July 2023). Archived from the original on 27 August 2023. Retrieved 27 August 2023.
  3. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 Mueller L, Klaiber A, Ley L, Becker AM, Thomann J, Luethi D, et al. (July 2025). "Pharmacokinetics, Pharmacodynamics, and Urinary Recovery of Oral Mescaline Hydrochloride in Healthy Participants". Clinical Pharmacokinetics. 64 (10): 1495–1506. doi:10.1007/s40262-025-01544-x. PMC 12479620. PMID 40658345. The low affinity of mescaline for 5-HT2A receptors [3] and poor blood–brain barrier permeability [20] contribute to the comparatively high oral doses of 300–800 mg of mescaline hydrochloride (HCl) that are typically required to induce a full psychedelic experience in humans compared with psilocybin dihydrate (20–40 mg) and LSD base (100–200 µg) [5, 21]. [...] We found that acute subjective efects of mescaline were closely linked to the plasma mescaline concentrations but occurred with a delay as seen in the counterclockwise hysteresis. Accordingly, our modeling approach that used an efect compartment that was connected to the plasma mescaline concentration using a frst-order equilibrium rate constant (ke0) adequately described the observed acute efects. This finding is consistent with a delayed central distribution of mescaline.
  4. 1 2 3 4 "Mescaline: Uses, Interactions, Mechanism of Action". DrugBank Online. 3 July 2024. Retrieved 19 May 2025.
  5. 1 2 3 Dart RC (2004). Medical Toxicology (3 ed.). Lippincott Williams & Wilkins. p. 1706. ISBN 978-0-7817-2845-4. Archived from the original on 29 March 2022. Mescaline binds to liver proteins but not to plasma proteins. It is rapidly and widely distributed into the peripheral tissues. The volume of distribution is not specifically known but is believed to be on the order of several L/kg.
  6. 1 2 Oh YH, Leitch WE, Axelrod S, Small SM, Winzler RJ, Sanders BE (May 1967). "Binding of biologically active amines to plasma protein fractions". Biochemical Pharmacology. 16 (5): 849–861. doi:10.1016/0006-2952(67)90058-5. PMID 6036735. Studies have been initiated to provide information on biochemical relationships between biogenic amines and plasma proteins. The binding in vitro of several biogenic amines, i.e. 3,4-dimethoxyphenylethylamine, mescaline, tyramine, and normetanephrine, labeled with 14C or 3H to human plasma protein fractions have been studied. [...] No appreciable binding to any of the plasma protein fractions was observed with mescaline or normetanephrine. [...]
  7. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 Cassels BK, Sáez-Briones P (October 2018). "Dark Classics in Chemical Neuroscience: Mescaline". ACS Chemical Neuroscience. 9 (10): 2448–2458. doi:10.1021/acschemneuro.8b00215. PMID 29847089.
  8. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 Doesburg-van Kleffens M, Zimmermann-Klemd AM, Gründemann C (December 2023). "An Overview on the Hallucinogenic Peyote and Its Alkaloid Mescaline: The Importance of Context, Ceremony and Culture". Molecules. 28 (24). Basel, Switzerland: 7942. doi:10.3390/molecules28247942. PMC 10746114. PMID 38138432.
  9. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 Holze F, Singh N, Liechti ME, D'Souza DC (May 2024). "Serotonergic Psychedelics: A Comparative Review of Efficacy, Safety, Pharmacokinetics, and Binding Profile". Biological Psychiatry. Cognitive Neuroscience and Neuroimaging. 9 (5): 472–489. doi:10.1016/j.bpsc.2024.01.007. PMID 38301886.
  10. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 Klaiber A, Schmid Y, Becker AM, Straumann I, Erne L, Jelusic A, et al. (September 2024). "Acute dose-dependent effects of mescaline in a double-blind placebo-controlled study in healthy subjects". Translational Psychiatry. 14 (1) 395. doi:10.1038/s41398-024-03116-2. PMC 11442856. PMID 39349427. [...] a 500 mg dose of mescaline hydrochloride produced comparable effects to 100 µg LSD base or 20 mg psilocybin dihydrate when they were compared within the same study and subjects [14]; [...] Dosages ranging from 178 to 356 mg of mescaline hydrochloride are considered moderate [36].
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  17. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. https://erowid.org/library/books_online/pihkal/pihkal096.shtml
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  41. 1 2 Rouhier A (1927). Le Peyotl: La Plante Qui Fait les Yeux Émerveillés [Peyote: The Plant That Fills the Eyes with Marvels] (in French). Doin. Archived from the original on 14 March 2024. Retrieved 26 June 2026.
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  56. ↑ Underhill R (1 May 1957). "Religion Among American Indians". The Annals of the American Academy of Political and Social Science. 311 (1): 127–136. doi:10.1177/000271625731100114. To produce any bad effects such as shortened respiration, at least 350 mgs. of mescaline are needed; white experimenters have taken as many as 700 without harm. The standard buttons (eight) taken at meetings contain only some 107 mgs.
  57. ↑ Buckingham J (2014). "Mescaline". Dictionary of Natural Products: 254–260.
  58. ↑ Slothower JD, Wiegand TJ (2014). "Mescaline". In Wexler P (ed.). Encyclopedia of Toxicology (3rd ed.). Academic Press. pp. 221–222. doi:10.1016/B978-0-12-386454-3.00747-8. ISBN 978-0-12-386455-0. There have been no reported deaths due to the physiological effects of peyote/mescaline. Traumatic deaths have occurred secondary to hallucinations.
  59. ↑ Schultes RE (1938). "The Appeal of Peyote (Lophophora Williamsii) as a Medicine". American Anthropologist. 40 (4): 698–715. doi:10.1525/aa.1938.40.4.02a00100. In the ceremony, peyote is eaten dry, but occasionally fresh plants are consumed.16 The dried mescal buttons keep indefinitely and are stored in bags for use. They possess a very bitter taste, but in spite of this, they are chewed and swallowed in great number by peyotists. The smallest consumption by a single person is about four buttons at each meeting. It is impossible to estimate the largest, but I have seen an Indian eat more than thirty at one ceremony. Other investigators17 report doses as large as ninety buttons. An estimate of the average consumption, however, would probably be about twelve buttons by each person at a single meeting.
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  127. ↑ Klein MT, Kalam M, Trout K, Fowler N, Terry M (2015). "Mescaline Concentrations in Three Principal Tissues of Lophophora williamsii (Cactaceae): Implications for Sustainable Harvesting Practices". Haseltonia. 131 (2). Elsevier BV: 34–42. Bibcode:2015Hasel..20...34K. doi:10.2985/026.020.0107. S2CID 32474292.
  128. ↑ Crosby DM, McLaughlin JL (December 1973). "Cactus alkaloids. XIX. Crystallization of mescaline HCl and 3-methoxytyramine HCl from Trichocereus pachanoi" (PDF). Lloydia. 36 (4): 416–418. PMID 4773270. Retrieved 13 December 2013.
  129. ↑ "Mescaline in Trichocereus". The Mescaline Garden. Archived from the original on 8 August 2024. Retrieved 9 August 2024.
  130. ↑ Van Der Sypt F (3 April 2022). "Validation and exploratory application of a simple, rapid and economical procedure (MESQ) for the quantification of mescaline in fresh cactus tissue and aqueous cactus extracts". PhytoChem & BioSub Journal. doi:10.5281/zenodo.6409376.
  131. 1 2 3 4 Bruhn JG, Holmstedt B (1973). "Early peyote research an interdisciplinary study". Economic Botany. 28 (4): 353–390. doi:10.1007/BF02862854. ISSN 0013-0001. The spark that was to ignite the "peyote boom" was not lit until 1887 when Briggs published the first study of the effects of "muscale buttons". [...] Early peyote research is closely connected with the name of Louis Lewin. However, he was not the discoverer of the drug. Credit for having brought peyote to the attention of the medical world of the 1880's must go to Dr. John Raleigh Briggs of Dallas, Texas. An instrumental role was also played by the pharmaceutical manufacturers Parke, Davis & Company of Detroit. [...] Mrs. Nickels was long considered to be the first supplier of "mescal buttons" for scientific study, but Slotkin (1955, p. 222, note 7) rejected this and pointed out that Briggs was the pioneer (cf. Bender, 1968). [...] In 1894, however, Prentiss and Morgan (1895) of the Medical Department of Columbian University in Washington obtained a large supply of mescal buttons through James Mooney, "agent among the Indians". They described six experiments in man with the crude drug. "The production of visions" was the most interesting effect found, and the authors concluded that the action of Anhalonium lewinii was not identical with that of any other drug. Except for Briggs' early (and somewhat dubious) self-experiment, these were the first reported studies of the drug in man. [...] The first person to draw the attention of the scientific world to peyote was doubtless Dr. J. R. Briggs, and not Mrs. A. B. Nickels as is often stated.
  132. 1 2 Lundström J (June 1971). "Biosynthetic studies on mescaline and related cactus alkaloids". Acta Pharmaceutica Suecica. 8 (3): 275–302. PMID 5560272.
  133. ↑ Forbes TD, Clement BA. "Chemistry of Acacia's from South Texas" (PDF). Texas A&M Agricultural Research & Extension Center at Uvalde. Archived from the original (PDF) on 15 May 2011.
  134. ↑ Keeper Trout (16 January 2015). "Acacia species with data conflicts". sacredcacti.com. Retrieved 13 March 2021.
  135. 1 2 Kulma A, Szopa J (March 2007). "Catecholamies are active compounds in plants". Plant Science. 172 (3): 433–440. Bibcode:2007PlnSc.172..433K. doi:10.1016/j.plantsci.2006.10.013.
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  137. ↑ Rosengarten H, Friedhoff AJ (1976). "A review of recent studies of the biosynthesis and excretion of hallucinogens formed by methylation of neurotransmitters or related substances". Schizophrenia Bulletin. 2 (1): 90–105. doi:10.1093/schbul/2.1.90. PMID 779022.
  138. ↑ Ruiz de Alarcón H (1984). Treatise on the Heathen Superstitions that Today Live Among the Indians Native to this New Spain, 1629. University of Oklahoma Press. ISBN 978-0-8061-2031-7.
  139. ↑ Socha DM, Sykutera M, Orefici G (1 December 2022). "Use of psychoactive and stimulant plants on the south coast of Peru from the Early Intermediate to Late Intermediate Period". Journal of Archaeological Science. 148 105688. Bibcode:2022JArSc.14805688S. doi:10.1016/j.jas.2022.105688. ISSN 0305-4403. S2CID 252954052.
  140. ↑ Bussmann RW, Sharon D (November 2006). "Traditional medicinal plant use in Northern Peru: tracking two thousand years of healing culture". Journal of Ethnobiology and Ethnomedicine. 2 47. doi:10.1186/1746-4269-2-47. PMC 1637095. PMID 17090303.
  141. ↑ Armijos C, Cota I, González S (February 2014). "Traditional medicine applied by the Saraguro yachakkuna: a preliminary approach to the use of sacred and psychoactive plant species in the southern region of Ecuador". Journal of Ethnobiology and Ethnomedicine. 10 26. doi:10.1186/1746-4269-10-26. PMC 3975971. PMID 24565054.
  142. ↑ Samorini G (1 June 2019). "The oldest archeological data evidencing the relationship of Homo sapiens with psychoactive plants: A worldwide overview". Journal of Psychedelic Studies. 3 (2): 63–80. doi:10.1556/2054.2019.008. S2CID 135116632.
  143. ↑ El-Seedi HR, De Smet PA, Beck O, Possnert G, Bruhn JG (October 2005). "Prehistoric peyote use: alkaloid analysis and radiocarbon dating of archaeological specimens of Lophophora from Texas". Journal of Ethnopharmacology. 101 (1–3): 238–242. doi:10.1016/j.jep.2005.04.022. PMID 15990261.
  144. 1 2 Briggs JR (8 April 1887). ""Muscale Buttons"—Physiological Effects—Personal Experience". The Medical Register. 1: 267–268. Archived from the original on 5 April 2025.
  145. 1 2 3 4 Daniel M. Perrine (2001). "Visions of the Night Western Medicine Meets Peyote 1887-1899" (PDF). The Heffter Review of Psychedelic Research. 2: 6–52.
  146. ↑ "Arthur Heffter". Character Vaults. Erowid.org. Retrieved 9 January 2013.
  147. 1 2 3 McKenna T (1999). "[Chapter 14:] A Brief History of Psychedelics". Food of the Gods: The Search for the Original Tree of Knowledge: a Radical History of Plants, Drugs and Human Evolution (PDF). Rider. pp. 223–245. ISBN 978-0-7126-7038-8.
  148. ↑ Dubus Z, Grandgeorge E, Verroust V (2023). "History of the administration of psychedelics in France". Frontiers in Psychology. 14 1131565. doi:10.3389/fpsyg.2023.1131565. PMC 10513055. PMID 37744588. In the 1920s, the pharmacologist Alexandre Rouhier captured the attention of the French and international scientific communities, first through his important monograph on the uses of peyote, which was translated several times, and later through his pharmaceutical preparations. [...] Alexandre Rouhier: the totality of peyote's alkaloids, for a polyvalent therapeutic action: The 1927 appearance of pharmacist Alexandre Rouhier's Le Peyotl: la plante qui fait les yeux émerveillés (Peyote: The Plant That Fills the Eyes with Marvels) was a success considering its somewhat obscure subject matter (Rouhier, 1927). [...]
  149. ↑ Frederking W (September 1953). "Über die Verwendung von Rauschdrogen (Meskalin und Lysergsäurediaethylamid) in der Psychotherapie" [The use of narcotics (mescaline and lysergic acid diethylamide) in psychotherapy]. Psyche (Stuttg) (in German). 7 (6): 342–364. PMID 13112311.
  150. ↑ Frederking W (March 1955). "Intoxicant drugs (mescaline and lysergic acid diethylamide) in psychotherapy". The Journal of Nervous and Mental Disease. 121 (3): 262–266. doi:10.1097/00005053-195503000-00010. PMID 14381913.
  151. ↑ Dyck E (1 April 2025). "History of Psychedelics: An Overview". South Atlantic Quarterly. 124 (2): 295–305. doi:10.1215/00382876-11626609. ISSN 0038-2876.
  152. 1 2 Walker SR, Pullella GA, Piggott MJ, Duggan PJ (17 July 2023). "Introduction to the chemistry and pharmacology of psychedelic drugs". Australian Journal of Chemistry. 76 (5): 236–257. doi:10.1071/CH23050. ISSN 0004-9425. In 1955, mescaline (4) even gained the attention of British politician Christopher Mayhew, who participated in an 'experiment' in which he was recorded after being administered mescaline (4). The footage of Mayhew was to be televised on the BBC programme Panorama; however, the broadcaster decided against airing it. Mayhew later described the experiment as 'the most interesting thing [he has] ever done' and 'profoundly thought-provoking'.[80]
  153. 1 2 "The History Hour, Why a British MP was filmed taking mescaline". BBC. 15 May 2021. Retrieved 26 June 2026.
  154. 1 2 "Panorama: The Mescaline Experiment". February 2005. Archived from the original on 26 July 2012.
  155. ↑ Daly M (15 May 2019). "The Fascinating History of Mescaline, the OG Psychedelic". VICE. VICE. Retrieved 26 June 2026.
  156. 1 2 3 4 Falcon J (2025). "Anthropology of Psychedelics". Anthropology of Consciousness. 36 (2). doi:10.1111/anoc.70002. ISSN 1053-4202.
  157. 1 2 Heffter A (1898). "Ueber Pellote: Beiträge zur chemischen und pharmakologischen Kenntniss der Cacteen Zweite Mittheilung" [About Pellote: Contributions to the chemical and pharmacological knowledge of cacti, second communication]. Archiv für Experimentelle Pathologie und Pharmakologie (in German). 40 (5–6): 385–429. doi:10.1007/BF01825267. ISSN 0028-1298.
  158. ↑ Metzer WS (February 1989). "The experimentation of S. Weir Mitchell with mescal". Neurology. 39 (2 Pt 1): 303–304. doi:10.1212/wnl.39.2.303. PMID 2644583.
  159. ↑ Mitchell SW (December 1896). "Remarks on the Effects of Anhelonium Lewinii (the Mescal Button)". British Medical Journal. 2 (1875): 1625–1629. doi:10.1136/bmj.2.1875.1625. PMC 2511273. PMID 20756623.
  160. ↑ Ellis H (1898). "Mescal: A New Artificial Paradise". The Contemporary Review. Vol. LXXIII.
  161. ↑ Rudgley R (1993). "VI". The Alchemy of Culture: Intoxicants in Society. British Museum Press. ISBN 978-0-7141-1736-2.
  162. ↑ Giannini AJ (1997). Drugs of Abuse (Second ed.). Los Angeles: Practice Management Information Corp. ISBN 978-1-57066-053-5.
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  165. 1 2 3 Jay M (21 August 2019). "Sartre's Bad Trip by Mike Jay". The Paris Review. Retrieved 25 May 2026.
  166. 1 2 3 Allen-Mills T (22 November 2009). "Mescaline left Jean Paul Sartre in the grip of lobster madness". The Times. The Sunday Times. Retrieved 25 May 2026.
  167. ↑ Doyle P (20 May 2019). "Patti Smith Channels French Poet Antonin Artaud on Peyote". Rolling Stone. Retrieved 3 April 2022.
  168. ↑ Jane Kramer (10 August 1968). "The Father of Flower Power". The New Yorker. Retrieved 3 April 2022.
  169. ↑ Witkiewicz SI, Biczysko S (1932). Nikotyna, alkohol, kokaina, peyotl, morfina, eter+ appendix. Warsaw: Drukarnia Towarzystwa Polskiej Macierzy Szkolnej.
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  172. ↑ Bauer BE (2 December 2019). "Mescaline". Psychedelic Science Review. Psychedelic Science Review. Retrieved 30 October 2023.
  173. ↑ Bird M (2012). 100 Ideas that Changed Art. London: Laurence King Publishing.
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  175. ↑ Greene A (1989). "Dazed and Confused: 10 Classic Drugged-Out Shows". Rolling Stone. Santana at Woodstock, 1969 - Mescaline
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  178. ↑ "FLOW MY Tears". www.philipkdickfans.com. Retrieved 4 May 2018.
  179. ↑ Doblin R (June 2001). Regulation of the Medical Use of Psychedelics and Marijuana (Ph.D. thesis). Harvard University. In 1927, German physician Kurt Beringer published a description of his mescaline studies in research subjects.70 One subject of his, who reportedly felt that the remarkable visual images he experienced should be captured in film, was subsequently hired by Walt Disney as the chief visualist for the Disney film, Fantasia.71
  180. ↑ "The Matrix Quotes". imdb.com. Neo: You ever have that feeling where you're not sure if you're awake or still dreaming? Choi: All the time. It's called mescaline, it's the only way to fly.
  181. ↑ United States Department of Justice (1 July 2026). "Drug Scheduling". Archived from the original on 20 October 2008. Retrieved 2 November 2007.
  182. ↑ "List of psychotropic substances under international control" (PDF). International Narcotics Control Board. Archived from the original (PDF) on 5 December 2005. Retrieved 27 January 2008.
  183. ↑ "City of Boerne v. Flores". Federal Judicial Center. Retrieved 18 March 2025.
  184. ↑ "State v. Mooney". utcourts.gov. Retrieved 5 October 2012.
  185. ↑ "Colorado Proposition 122, Decriminalization and Regulated Access Program for Certain Psychedelic Plants and Fungi Initiative (2022)".
  186. ↑ Gupta RC (2018). Veterinary Toxicology: Basic and Clinical Principles (Third ed.). Academic Press. pp. 363–390. ISBN 978-0-12-370467-2.
  187. ↑ "2007 U.K. Trichocereus Cacti Legal Case Regina v. Saul Sette". Erowid.org. June 2007. Retrieved 6 April 2012.
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  196. ↑ Copes H, Hochstetler A, Ragland J, Hendricks PS (2026). "Hitting the Reset Button: Ceremonial Use of Peyote and Experiences of Personal Change". Journal of Drug Issues. 56 (1): 150–170. doi:10.1177/00220426241274737. ISSN 0022-0426.
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