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Mescaline



 
 
Mescaline or 3,4,5-trimethoxyphenethylamine is a naturally-occurring psychedelic
Psychedelic

The word 'psychedelic' is an English term coined from the Greek language words for "soul," ???? , and "manifest," d???? . A psychedelic experience is characterized by the perception of aspects of one's mind previously unknown, or by the creative exuberance of the mind liberated from its ostensibly ordinary fetters....
 alkaloid
Alkaloid

Alkaloids are naturally occurring chemical compounds containing base nitrogen atoms. The name derives from the word alkaline and was used to describe any nitrogen-containing base....
 of the phenethylamine
Phenethylamine

Phenethylamine, or ?-phenylethylamine or 2-phenylethylamine, is an alkaloid and monoamine. Phenethylamine also has a constitutional isomer a-phenylethylamine , which has two stereoisomers: --1-phenylethylamine and --1-phenylethylamine....
 class. It is mainly used as a recreational drug, an entheogen
Entheogen

An entheogen , in the strictest sense, is a psychoactive substance used in a religion or shamanism context. Historically, entheogens are derived primarily from plant sources and have been used in a variety of traditional religious contexts....
, and a tool
Tool

A broad definition of a tool is an entity used to interface between two or more domains that facilitates more effective action of one domain upon the other....
 to supplement various practices for transcendence
Transcendence (philosophy)

In philosophy, the adjective transcendental and the noun transcendence convey three different but related primary meanings, all of them derived from the word's literal meaning , of climbing or going beyond: one sense that originated in Ancient philosophy, one in Medieval philosophy, and one in modern philosophy....
, including in meditation
Meditation

Meditation is a mental discipline by which one attempts to get beyond the reflexive, "thinking" mind into a deeper state of relaxation or awareness....
, psychonautics, art
Art

Art is the process or product of deliberately arranging elements in a way that appeals to the senses or emotions. It encompasses a diverse range of human activities, creations, and modes of expression, including music and literature....
 projects, and psychedelic psychotherapy
Psychedelic psychotherapy

Psychedelic therapy refers to therapy practices involving the use of psychedelic drugs, particularly serotonergic psychedelics such as Lysergic acid diethylamide, psilocin and Dimethyltryptamine....
.

It occurs naturally in the peyote cactus (Lophophora williamsii), the San Pedro cactus (Echinopsis pachanoi) and the Peruvian Torch cactus
Peruvian Torch cactus

Peruvian Torch cactus is a fast-growing columnar cactus native to the western slope of the Andes in Peru, between about 2000-3000 meters above sea level....
 (Echinopsis peruviana), and in a number of other members of the Cactaceae.






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Encyclopedia


Mescaline or 3,4,5-trimethoxyphenethylamine is a naturally-occurring psychedelic
Psychedelic

The word 'psychedelic' is an English term coined from the Greek language words for "soul," ???? , and "manifest," d???? . A psychedelic experience is characterized by the perception of aspects of one's mind previously unknown, or by the creative exuberance of the mind liberated from its ostensibly ordinary fetters....
 alkaloid
Alkaloid

Alkaloids are naturally occurring chemical compounds containing base nitrogen atoms. The name derives from the word alkaline and was used to describe any nitrogen-containing base....
 of the phenethylamine
Phenethylamine

Phenethylamine, or ?-phenylethylamine or 2-phenylethylamine, is an alkaloid and monoamine. Phenethylamine also has a constitutional isomer a-phenylethylamine , which has two stereoisomers: --1-phenylethylamine and --1-phenylethylamine....
 class. It is mainly used as a recreational drug, an entheogen
Entheogen

An entheogen , in the strictest sense, is a psychoactive substance used in a religion or shamanism context. Historically, entheogens are derived primarily from plant sources and have been used in a variety of traditional religious contexts....
, and a tool
Tool

A broad definition of a tool is an entity used to interface between two or more domains that facilitates more effective action of one domain upon the other....
 to supplement various practices for transcendence
Transcendence (philosophy)

In philosophy, the adjective transcendental and the noun transcendence convey three different but related primary meanings, all of them derived from the word's literal meaning , of climbing or going beyond: one sense that originated in Ancient philosophy, one in Medieval philosophy, and one in modern philosophy....
, including in meditation
Meditation

Meditation is a mental discipline by which one attempts to get beyond the reflexive, "thinking" mind into a deeper state of relaxation or awareness....
, psychonautics, art
Art

Art is the process or product of deliberately arranging elements in a way that appeals to the senses or emotions. It encompasses a diverse range of human activities, creations, and modes of expression, including music and literature....
 projects, and psychedelic psychotherapy
Psychedelic psychotherapy

Psychedelic therapy refers to therapy practices involving the use of psychedelic drugs, particularly serotonergic psychedelics such as Lysergic acid diethylamide, psilocin and Dimethyltryptamine....
.

It occurs naturally in the peyote cactus (Lophophora williamsii), the San Pedro cactus (Echinopsis pachanoi) and the Peruvian Torch cactus
Peruvian Torch cactus

Peruvian Torch cactus is a fast-growing columnar cactus native to the western slope of the Andes in Peru, between about 2000-3000 meters above sea level....
 (Echinopsis peruviana), and in a number of other members of the Cactaceae. It is also found in small amounts in certain members of the Fabaceae
Fabaceae

Fabaceae or Leguminosae is a large and economically important family of flowering plants, which is commonly known as the legume family, pea family, bean family or pulse family....
 (bean family), including Acacia berlandieri
Acacia berlandieri

Acacia berlandieri is a shrub native to the Southwestern United States that belongs to the subfamily Mimosoideae of Fabaceae . It grows tall, with blossoms that are spherical and white, occurring from February through April....
. Mescaline was first isolated and identified in 1897 by the German
German Empire

The German Empire is the name commonly used in English to describe Germany from the unification of Germany and proclamation of William I, German Emperor as German Emperor on 18 January 1871, to 1918, when it became Weimar republic after defeat in World War I and the abdication of William II, German Emperor ....
 Arthur Heffter
Arthur Heffter

Arthur Heffter was a Germany pharmacology and chemist. He isolated mescaline from the peyote cactus in 1897, the first such isolation of a naturally occurring psychedelic substance in pure form....
 and first synthesized in 1919 by Ernst Späth
Ernst Späth

Ernst Sp?th in Zurich) was a Austrian chemist.He was the first to synthesise Mescaline.He lost everything in World War II, and died with no money....
.

History and usage


The use of peyote in Native American
Indigenous peoples of the Americas

The indigenous peoples of the Americas are the pre-Columbian inhabitants of the Americas, their descendants, and many ethnic groups who identify with those peoples....
 religious ceremonies has been noted since the earliest European contact, notably by the Huichol
Huichol

The Huichol or Wix?ritari are an indigenous ethnic group of western central Mexico, living in the Sierra Madre Occidental range in the Mexican states of Nayarit, Jalisco, Zacatecas, and Durango....
s in Mexico
Mexico

The United Mexican States , commonly known as Mexico , is a federalism constitutionalism republic in North America. It is bordered on the north by the United States; on the south and west by the Pacific Ocean; on the southeast by Guatemala, Belize, and the Caribbean Sea; and on the east by the Gulf of Mexico....
, but other cacti such as the San Pedro have been used in different regions, from Peru to Ecuador.

Aldous Huxley
Aldous Huxley

Aldous Leonard Huxley was an English writer and one of the most prominent members of the famous Huxley family. He spent the later part of his life in the United States, living in Los Angeles from 1937 until his death in 1963....
 experimented with the use of mescaline. So did Aleister Crowley
Aleister Crowley

Aleister Crowley, born Edward Alexander Crowley , , was a United Kingdom occultist, writer, mountaineering, poet, and yogi. He was an influential member of several occult organizations, including the Hermetic Order of the Golden Dawn, the A?A?, and Ordo Templi Orientis , and is best known today for his Works of Aleister Crowley, especi...
 as reported in his diary, as well as the famous sex psychologist Havelock Ellis
Havelock Ellis

Henry Havelock Ellis was a United Kingdom sexology, physician, and social reformer....
. By coincidence or experimentation, mescaline may have played a part in the development of the Cubist school of abstract art
Abstract art

Abstract art uses a visual language of form, color and line to create a composition which may exist with a degree of independence from visual references in the world....
. When George Braque and Pablo Picasso
Pablo Picasso

Pablo Diego Jos? Francisco de Paula Juan Nepomuceno Mar?a de los Remedios Cipriano de la Sant?sima Trinidad Ruiz y Picasso was a Spanish people Painting, drawing, and Sculpture....
 published the "Cubist Manifesto" they described design paradigms which were similar to visual experiences induced by mescaline and other rare drugs known to the South American Islanders.

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 disk-shaped buttons. Buttons are chewed to produce the effects or soaked in water for an intoxicating drink. However, the taste of the cactus is bitter, so users will often grind it into a powder and fill them in capsules to avoid having to taste it. The effective human dosage is 300–500 milligrams of pure mescaline. Hallucinations occur at 300–600mg, which is the equivalent to approximately 9-20 small peyote buttons. The average 3 inch button contains about 25mg mescaline.

Pharmacokinetics


Although the ED50 is variable with dosage and individual, the LD50 has been measured in various animals and is reported as follows:

  • 212 mg/kg i.p. (mice)
  • 132 mg/kg i.p. (rats)
  • 328 mg/kg i.p. (guinea pigs)


It is reported that mescaline is 1000-3000 times less potent than LSD
LSD

Lysergic acid diethylamide, LSD, LSD-25, or acid, is a semisynthetic psychedelic drug of the ergoline family. Its unusual psychological effects, which include visuals of colored patterns behind the eyes in the mind, a sense of time distorting, and crawling geometric patterns, have made it one of the most widely known psyched...
, and 30 times less potent than psilocybin
Psilocybin

Psilocybin is a psychedelic drug indole of the tryptamine family, found in psilocybin mushrooms. It is present in List of Psilocybin mushrooms of fungi, including those of the genus Psilocybe, such as Psilocybe cubensis and liberty cap , but also reportedly isolated from a dozen or so other genera....
. About half the initial dosage is excreted after 6 hours, but some studies suggest that it is not metabolized at all before excretion.

Tolerance builds with repeated usage, and it is suggested that a cross-tolerance
Cross-tolerance

Cross-tolerance refers to a pharmacological phenomenon, in which a patient being treated with a drug exhibits a physiological resistance to that medication as a result of tolerance to a pharmacologically similar drug....
 can be developed with LSD
LSD

Lysergic acid diethylamide, LSD, LSD-25, or acid, is a semisynthetic psychedelic drug of the ergoline family. Its unusual psychological effects, which include visuals of colored patterns behind the eyes in the mind, a sense of time distorting, and crawling geometric patterns, have made it one of the most widely known psyched...
 and psilocin
Psilocin

Psilocin sometimes also spelled psilocine, psilocyn, or psilotsin, is a psychedelic drug mushroom alkaloid. It is found in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin....
.

Mescaline appears to not be subject to metabolism by CYP2D6
CYP2D6

Cytochrome P450 2D6 , a member of the cytochrome P450 mixed-function oxidase system, is one of the most important enzymes involved in the metabolism of xenobiotics in the body....
 and between 20 and 50% of mescaline is excreted in the urine unchanged, and the rest being excreted as the carboxylic acid
Carboxylic acid

Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the Chemical formula -COH, usually written -COOH or -CO2H....
 form of mescaline, a likely result of MAO
Mao

, is a Japanese remake of the Korean suspense drama series titled Ma Wang which aired on Korean Broadcasting System in 2007. The drama stars Satoshi Ohno of Arashi and Toma Ikuta, both under the talent agency Johnny & Associates....
 degradation.

Behavioral and non-behavioral effects


Hallucination
Hallucination

A hallucination, in the broadest sense, is a perception in the absence of a stimulus . In a stricter sense, hallucinations are defined as perceptions in a conscious and awake state in the absence of external stimuli which have qualities of real perception, in that they are vivid, substantial, and located in external objective space....
s produced by mescaline are somewhat different from those of LSD
LSD

Lysergic acid diethylamide, LSD, LSD-25, or acid, is a semisynthetic psychedelic drug of the ergoline family. Its unusual psychological effects, which include visuals of colored patterns behind the eyes in the mind, a sense of time distorting, and crawling geometric patterns, have made it one of the most widely known psyched...
. Hallucinations are consistent with actual experience, but are typically intensifications of the stimulus properties of objects and sounds. Prominence of color is distinctive, appearing brilliant and intense. Placing a strobing light in front of closed eyelids can produce brilliant visual effects at the peak of the experience. Recurring visual patterns observed during the mescaline experience include stripes, checkerboards, angular spikes, multicolored dots, and very simple fractals which turn very complex. Aldous Huxley described these self transforming amorphous shapes as like animated stained glass illuminated from light coming through the eyelids. Like LSD
LSD

Lysergic acid diethylamide, LSD, LSD-25, or acid, is a semisynthetic psychedelic drug of the ergoline family. Its unusual psychological effects, which include visuals of colored patterns behind the eyes in the mind, a sense of time distorting, and crawling geometric patterns, have made it one of the most widely known psyched...
, mescaline induces distortions of form and kaleidoscopic
Kaleidoscope

A kaleidoscope is a tube of mirrors containing loose colored beads, pebbles or other small colored objects. The viewer looks in one end and light enters the other end, Reflection off the mirrors....
 experiences but which manifest more clearly with eyes closed and under low lighting conditions; however, all of these visual descriptions are purely subjective. And like with LSD, synesthesia
Synesthesia

Synesthesia ?from the Ancient Greek , "together," and , "sensation" ? is a neurologically based phenomenon in which stimulation of one sensory or cognitive pathway leads to automatic, involuntary experiences in a second sensory or cognitive pathway....
 can occur especially with the help of music. An unusual but unique characteristic of mescaline use is the "geometricization" of three-dimensional objects. The object can appear flattened and distorted, similar to the presentation of a Cubist painting.

Mescaline elicits a pattern of sympathetic arousal, with the peripheral nervous system
Peripheral nervous system

The peripheral nervous system resides or extends outside the central nervous system , which consists of the brain and spinal cord. The main function of the PNS is to connect the CNS to the limbs and organs....
 being a major target for this drug. Effects last for up to 12 hours.

Mode of action

Mescaline acts similarly to other psychedelic agents. Mescaline binds to, and activates the serotonin 5-HT2A receptor with a high nanomolar affinity. How activating the 5-HT2A receptor leads to hallucinations is still unknown, but it likely somehow involves exciting cortical
Cortex

Cortex may mean any of the following:In anatomy:* Cortex , the outermost or superficial layer of an organ, and especially in the brain:...
 neuron
Neuron

Neurons are responsive cell in the nervous system that process and transmit information by electrochemical Signal . They are the core components of the brain, the vertebrate spinal cord, the invertebrate ventral nerve cord, and the peripheral nerves....
s.

The exact mechanism of action for mescaline is unknown.

I know it says here on Wikipedia that it attaches itself to the 5-HT2A receptors but that is wrong and someone needs to change that! Mescaline is a phenethylamine and has a carbon skeleton and an oxygenation pattern that is similar to Dopamine and norepinephrine. Now I'm not a pharmacologists but even i know that you cant have a phenethylamine attach itself to a receptor that is meant for tryptamines only!

ill give you an example: is it possible to use the key from you Honda Civic to start your Chevy Silverado? of course not...

Status: Legality


In the US
United States

The United States of America is a Federal government constitutional republic comprising U.S. state and a federal district. The country is situated mostly in central North America, where its Contiguous United States and Washington, D.C., the Capital districts and territories, lie between the Pacific Ocean and Atlantic Oceans, Borders of the U...
 it was made illegal in 1970 by the Comprehensive Drug Abuse Prevention and Control Act
Controlled Substances Act

The Controlled Substances Act was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970....
. It was prohibited internationally by the 1971 Convention on Psychotropic Substances
Convention on Psychotropic Substances

The Convention on Psychotropic Substances is a United Nations treaty designed to control psychoactive drugs such as amphetamines, barbiturates, and psychedelics....
 and is categorized as a Schedule I hallucinogen by the CSA
Controlled Substances Act

The Controlled Substances Act was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970....
. Mescaline is only legal for certain natives (such as those involved in the Native American Church
Native American Church

Native American Church, a religious denomination which practices Peyotism or the Peyote religion, originated in the U.S. state of Oklahoma, and is the most widespread indigenous peoples religion among Native Americans ....
). Penalties for manufacture or sale can be as high as five years in prison and a fine of $15,000, with a penalty of up to one year and fine of $5000 for possession. In the UK, mescaline is a Class A drug (in powder form, although dried cactus can be bought and sold legally, unlike raw "magic" mushrooms, which are now illegal), and so carries the following penalties. For possession: up to seven years in prison or an unlimited fine or both. For dealing: up to life in prison or an unlimited fine or both. In 1990, the supreme court ruled that the state of Oregon could bar the use of mescaline in native American religious ceremonies. The religious freedom restoration act in 1993 allowed the use of peyote in religious ceremony but in 1997, the act was declared unconstitutional by the Supreme Court. Today the states have a right to choose whether peyote use in ceremony is legal.

Analogs


Mescaline has a number of analogs, featuring the methoxy
Methoxy

In chemistry , methoxy refers to the functional group consisting of a methyl group bound to oxygen. It has the formula:The word is used in organic nomenclature usually to describe an ether....
 groups altered to include thio
Thio

The Prefix thio-, when applied to a chemical, such as an ion, means that an oxygen atom in the compound has been replaced by a sulfur atom. This meaning is especially valid in organic chemistry....
 groups or to be extended. Examples include, but are not limited to, isomescaline
Isomescaline

Isomescaline, or 2,3,4-trimethoxyphenethylamine, is a lesser-known Psychedelics, dissociatives and deliriants. It is an isomer of mescaline, as well as an analog of TIM , TIM , and TIM ....
, thiomescaline
Thiomescaline

TM, or thiomescaline, is a series of lesser-known Psychedelics, dissociatives and deliriants similar in structure to mescaline. They were first synthesized by Alexander Shulgin and written up in his book PiHKAL....
, escaline
Escaline

Escaline is a psychedelic drug and entheogen of the phenethylamine class of compounds. Escaline was first synthesized and reported in the scientific literature by Benington, et al, in 1954, but was later re-examined in the laboratory of David E....
, thioescaline
Thioescaline

TE, or thioescaline, is a series of lesser-known Psychedelics, dissociatives and deliriants similar in structure to escaline. They were first synthesized by Alexander Shulgin and written up in his book PiHKAL....
, proscaline
Proscaline

Proscaline, or 4-propoxy-3,5-DMPEA is a psychedelic and hallucinogenic drug, used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs mescaline and escaline....
, isoproscaline
Isoproscaline

Isoproscaline or 4--isopropyl-3,5-dimethoxyphenethylamine is an analogue of mescaline. It is closely related to proscaline and was first synthesized by David E....
, buscaline
Buscaline

Buscaline, or 3,5-dimethoxy-4-Butyloxyphenethylamine, is a lesser-known Psychedelics, dissociatives and deliriants. It is an analog of mescaline....
, thiobuscaline
Thiobuscaline

Thiobuscaline, or 3,5-dimethoxy-4-butylthiophenethylamine, is a lesser-known Psychedelics, dissociatives and deliriants. It is an analog of buscaline....
, thioisomescaline, phenescaline
Phenescaline

Phenescaline, or 3,5-dimethoxy-4-phenylethoxyphenethylamine, is a lesser-known Psychedelics, dissociatives and deliriants. It is an analog of mescaline....
, symbescaline
Symbescaline

Symbescaline, or 3,5-diethoxy-4-methoxyphenethylamine, is a lesser-known Psychedelics, dissociatives and deliriants. It is a isomer of asymbescaline....
, asymbescaline
Asymbescaline

Asymbescaline, or 3,4-diethoxy-5-methoxyphenethylamine, is a lesser-known Psychedelics, dissociatives and deliriants. It is a homologue of Mescaline....
, thioasymbescaline, allylescaline
Allylescaline

Allylescaline, or 4-allyloxy-3,5-dimethoxyphenethylamine, is a lesser-known Psychedelics, dissociatives and deliriants. It is closely related in structure to mescaline....
, methallylescaline
Methallylescaline

Methallylescaline, or 4-methylallyloxy-3,5-dimethoxyphenethylamine, is a lesser-known Psychedelics, dissociatives and deliriants. It is also the 4-methyl Analog of allylescaline....
, metaescaline
Metaescaline

Metaescaline, or 3,4-dimethoxy-5-ethoxyphenethylamine, is a lesser-known Psychedelics, dissociatives and deliriants. It is an analog of mescaline....
, and thiometaescaline. It has an active amphetamine homolog, 3,4,5-trimethoxyamphetamine.

See also


  • The Doors of Perception
    The Doors of Perception

    The Doors of Perception is a 1954 book by Aldous Huxley detailing his experiences when taking mescaline.The title comes from William Blake's The Marriage of Heaven and Hell:...
  • Project MKULTRA
    Project MKULTRA

    Project MK-ULTRA, or MKULTRA, was the code name for a covert Central Intelligence Agency mind-control and Truth drug research program, run by the Central Intelligence Agency Directorate of Science & Technology....
  • PiHKAL
    PiHKAL

    PiHKAL is a 1991 book by Dr. Alexander Shulgin and Ann Shulgin about psychedelic phenethylamines. The full title of the book is Phenethylamines i Have Known And Loved: A Chemical Love Story....
  • Psychoactive drug
    Psychoactive drug

    A psychoactive drug or psychotropic substance is a chemical substance that acts primarily upon the central nervous system where it alters brain function, resulting in temporary changes in perception, mood , consciousness and behaviour....


External links

  • , an essay by Alexander Shulgin
    Alexander Shulgin

    Alexander "Sasha" Shulgin is a Russian-American pharmacologist, chemist and psychoactive drug developer.Shulgin is credited with the popularization of Methylenedioxymethamphetamine in the late 1970s and early 1980s, especially for psychopharmacology use and the treatment of depression and post-traumatic stress disorder....