Bill Wilson used LSD
Lysergic acid diethylamide - Lysergic acid diethylamide
2D structural formula and 3D models of LSD
|pronunciation||/ daɪ eθəl ˈæmaɪd /, / æmɪd / or / eɪmaɪd /|
|other names||LSD, LSD-25, Acid, Delysid, others|
|AHFS / Drugs.com||reference|
| Dependence |
| Addiction |
| ways |
|By mouth, under the tongue, intravenously|
|Drug class||Hallucinogen (serotonergic psychedelics)|
|Onset of action||30-40 minutes|
|Elimination half-life||3.6 hours|
|Duration of action||8–20 hours|
|IUPHAR / BPS|
|CompTox Dashboard (EPA)|
|Chemical and physical data|
|formula||C. 20 H 25 N 3 O.|
|molar mass||323.440 g mol –1|
|3D model (JSmol)|
|Melting point||80 to 85 ° C (176 to 185 ° F)|
Lysergic acid diethylamide ( LSD ), colloquially also as Known acid , is a hallucinogenic drug. Effects usually include altered thoughts, feelings, and awareness of one's surroundings. Many users have visual or auditory hallucinations. Dilated pupils, increased blood pressure and increased body temperature are typical. The effects usually start within half an hour and can last up to 20 hours. It is mainly used as a recreational drug or for spiritual reasons.
LSD doesn't seem to be addicting. Its frequent use can lead to acute tolerance and requires much larger doses to be felt. Unwanted psychiatric reactions such as anxiety, paranoia, and delusions are possible. Despite lack of use, distressing flashbacks can occur, a condition known as hallucinogen-persistent cognitive disorder. Death as a result of an LSD overdose is virtually unknown. However, in extremely rare cases, death can result from accidents or reckless behavior. It is believed that the effects of LSD are due to changes in the serotonin system. As little as 20 micrograms can have a noticeable effect. In its pure form, LSD is clear or white, has no odor, and is crystalline. It breaks down when exposed to ultraviolet light.
As of 2017, about 10 percent of people in the United States had used LSD at some point in their life, while 0.7 percent had used it in the last year. It was most popular in the 1960s through 1980s. Adult use of LSD in the United States increased 56.4% from 2015 to 2018. LSD is usually either swallowed or held under the tongue. It is most commonly sold on blotting paper and less often as tablets or in gelatin squares.
LSD was first made in 1938 by Albert Hofmann from lysergic acid, a chemical made from ergot, a fungus that grows on rye and other grains. Hofmann discovered its hallucinogenic properties in 1943. In the 1950s, the Central Intelligence Agency (CIA) believed the drug might be useful for mind control and tested it on people, some without their knowledge, in a program called MKUltra. LSD was sold as a research drug under the trade name Delysid in the 1950s and 1960s. It was listed as a List 1 controlled substance by the United Nations in 1971. No medical use is currently approved.
LSD is often used as a recreational drug with friends, in large quantities, or on its own.
LSD can catalyze intense spiritual experiences and is therefore considered an entheogen. Some users have reported out-of-body experiences. In 1966, Timothy Leary founded the League for Spiritual Discovery with LSD as a sacrament. Stanislav Grof wrote that religious and mystical experiences observed during the LSD sessions do not appear phenomenologically to be different from similar descriptions in the scriptures of the major world religions and the texts of ancient civilizations.
LSD does not currently have any approved uses in medicine. A meta-analysis concluded that a single dose was effective in reducing alcohol consumption in alcoholism. LSD has also been studied in depression, anxiety, and drug addiction with positive preliminary results.
LSD can cause dilated pupils, decreased appetite, profuse sweating, and wakefulness. Other physical responses to LSD are very diverse and non-specific, some of which may be secondary to the psychological effects of LSD. The reported symptoms include goose bumps, jaw grinding, dry mouth and hyperreflexia, increased body temperature, blood sugar and heart rate. Numbness, weakness, nausea and tremors have also been shown in negative experiences.
The most common immediate psychological effects of LSD are visual hallucinations and illusions (colloquially known as "trips"), which vary depending on how much is used and how the dosage interacts with the brain. Journeys usually begin within 20 to 30 minutes of oral ingestion of LSD (less if sniffed or taken intravenously), peak three to four hours after ingestion, and can last up to 20 hours in high doses. Users may also experience an "afterglow" of improved mood or perceived mental state for days or even weeks after ingestion with some experiences. Good travel is reportedly deeply stimulating and enjoyable, and typically involves intense joy or euphoria, a greater appreciation for life, less fear, a sense of spiritual enlightenment, and a sense of belonging or connectedness with the universe. Negative experiences, colloquially known as "bad trips", evoke a range of dark emotions, including irrational fear, fear, panic, paranoia, fear, suspicion, hopelessness, and even thoughts of suicide. While it is impossible to predict when a bad trip will take place, mood, surroundings, sleep, hydration, social environment, and other factors can all be controlled (colloquially referred to as "set and set") to reduce the risk of a bad trip Minimize travel.
LSD creates an animated sensory experience of the senses, emotions, memories, time and awareness for 6 to 20 hours, depending on dosage and tolerance. Generally, within 30 to 90 minutes of ingestion, the user can experience everything from subtle changes in perception to overwhelming cognitive shifts. Changes in auditory and visual perception are also typical.
Some sensory effects may include brighter or more vivid colors, objects and surfaces that appear to pucker, "breathe" or otherwise move, spinning fractals overlaid on one's eyesight, colored patterns behind closed eyelids Altered sense of time and geometric patterns include the emergence of walls and other structured objects and the transformation of objects. Some users also report a strong metallic taste for the duration of the effects. The texture or taste of foods may be different than when they are sober, and users may also have an aversion to foods they would normally enjoy. Similar effects were also found in rats.
Some report that the inanimate world seems inexplicably animated; For example, objects that are static in three dimensions can move relative to one or more additional spatial dimensions. Many of the basic visual effects are similar to the phosphenes observed after pressure on the eye and have also been studied as shape constants. Sometimes these effects and patterns can change if they are focused, or they can change based on thoughts, emotions, or music. The auditory effects of LSD can include echo-like sound distortions, changes in the ability to recognize simultaneous auditory and visual stimuli, and a general intensification of the musical experience. Higher doses often cause intense and fundamental distortions in sensory perception such as synesthesia, the experience of additional spatial or temporal dimensions, and temporary dissociation.
Of the 20 drugs that David Nutt ranked in order of individual and societal harm, LSD was the third to last, or about 1/10 as harmful as alcohol. The most significant side effect of LSD was mental impairment during intoxication.
LSD can trigger panic attacks or extreme anxiety, which is colloquially referred to as a "bad trip". Review studies suggest that LSD likely plays a role in triggering the onset of acute psychosis in previously healthy individuals, with an increased likelihood in those with a family history of schizophrenia. There is some evidence that people with severe mental illnesses such as schizophrenia are more likely to have adverse effects from taking LSD.
While publicly available documents indicate that the CIA and the Department of Defense have stopped research into the use of LSD as a mind control agent, research from the 1960s suggests that both mentally ill and healthy people are more suggestible under its influence.
"Flashbacks" are a reported psychological phenomenon in which a person experiences an episode of some of the subjective effects of LSD after the drug wears off and persists for months or years after hallucinogen use. People with a persistent hallucinogenic perception disorder experience intermittent or chronic flashbacks that lead to stress or impairment in life and work.
Cancer and pregnancy
The mutagenic potential of LSD is unclear. Overall, the evidence seems to suggest limited or no effect at frequently used doses. Studies have shown no evidence of teratogenic or mutagenic effects.
Addiction and tolerance
Tolerance to LSD builds up with consistent use, and cross-tolerance between LSD, mescaline, and psilocybin has been demonstrated. The researchers believe that tolerance returns to baseline after two weeks without drugs.
The NIH states that LSD is addicting while most other sources are not. A 2009 textbook states that it "rarely leads to compulsive use". A 2006 review said it was easily abused but not addictive.
A 2008 report found that while there had been no "comprehensive review" since the 1950s and "almost no legal clinical research" since the 1970s, there had been "no documented human deaths from an LSD overdose". Eight people who accidentally consumed very large amounts by mistaking LSD for cocaine developed comatose states, hyperthermia, vomiting, gastric bleeding, and breathing problems - but all survived with supportive care. Several behavioral deaths and suicides have occurred from LSD, according to recent reports. It is beneficial to have reassurance in a calm, safe environment. With benzodiazepines such as lorazepam or diazepam, movement can be tackled safely. Neuroleptics such as haloperidol, on the other hand, are recommended because they can have harmful effects. LSD is rapidly absorbed, so activated charcoal and gastric emptying are of little use unless done within 30 to 60 minutes of ingesting an LSD overdose. Sedation or physical restraint are rarely required, and excessive restraint can lead to complications such as hyperthermia (overheating) or rhabdomyolysis.
Massive doses "should be handled with supportive care, including respiratory support and endotracheal intubation if necessary. Hypertension [high blood pressure], tachycardia [rapid heartbeat], and hyperthermia should be treated symptomatically. Hypotension [low blood pressure] should be treated with fluids first, and then with." Need with pressing. "" Intravenous administration of anticoagulants, vasodilators, and sympatholytics may be useful in the treatment of ergotism ".
Most serotonergic psychedelics are not significantly dopaminergic and LSD is therefore atypical in this regard. The agonism of the D 2 Receptor through LSD may contribute to its psychoactive effects in humans.
LSD binds to most serotonin receptor subtypes with the exception of 5-HT 3 - and 5-HT 4 Receptors. However, most of these receptors are affected if the affinity is too low to be sufficiently activated by the brain concentration of about 10-20 nM. In humans, recreational doses of LSD 5-HT can be used 1A (K i = 1.1 nM), 5-HT 2A (K i = 2.9 nM), 5-HT 2 B (K i = 4.9 nM), 5-HT 2C (K i = 23 nM), 5-HT 5A (K i = 9 nM [in cloned rat tissues]) and 5-HT 6 Receptors (K i = 2.3 nM). Although not present in humans, 5-HT exhibit 5B- Receptors found in rodents also have high affinity for LSD. The psychedelic effects of LSD are due to the cross-activation of 5-HT 2A -Receptor heteromers returned. Many, but not all, of 5-HT 2A- Agonists are psychedelics and 5-HT 2A- Antagonists block the psychedelic activity of LSD. LSD shows functional selectivity on the 5-HT 2A and 5 - HT 2C - Receptors that it activates the signal transduction enzyme phospholipase A2 instead of activating the enzyme phospholipase C like the endogenous ligand serotonin does.
Exactly how LSD produces its effects is unknown, but it is believed that it works by increasing the release of glutamate in the cerebral cortex and thus arousal in this area, particularly in layers IV and V. LSD, like many other recreational drugs, has been shown to activate DARPP-32-related pathways. The drug enhances dopamine - D 2 Receptor protomer recognition and signaling by D 2 -5-HT 2A Receptor - complexes that contribute to their psychotic effects. LSD has been shown to have low affinity for H1 receptors and to exhibit antihistamine effects.
LSD is a biased agonist that induces a conformation in serotonin receptors that preferentially recruits β-arrestin over activating G proteins. LSD also has an exceptionally long dwell time when bound to serotonin receptors for hours, which is consistent with the long-lasting effects of LSD despite its relatively quick clearance. A crystal structure of 5-HT bound to LSD 2 B Figure 12 shows an extracellular loop that forms a lid over the diethylamide end of the binding cavity, which explains the slow rate of LSD delivery from serotonin receptors. The related lysergamide lysergic acid amide (LSA), which lacks the diethylamide unit, is far less hallucinogenic in comparison.
The effects of LSD usually last between 6 and 12 hours, depending on the dosage, tolerance, body weight and age. The Sandoz prospectus for "Delysid" warned: "Intermittent affect disorders can sometimes last for several days." Aghajanian and Bing (1964) found that LSD had an elimination half-life of only 175 minutes (about 3 hours). However, using more detailed techniques, Papac and Foltz (1990) reported that 1 µg / kg of oral LSD administered to a single male volunteer had an apparent plasma half-life of 5.1 hours with a maximum plasma concentration of 5 ng / ml at 3 had hours after ingestion.
The pharmacokinetics of LSD were not properly determined until 2015, which is not surprising for a drug with the low potency of LSD at low μg. In a sample of 16 healthy volunteers, a single oral dose of 200 μg of LSD in the middle range was found to have mean maximum concentrations of 4.5 ng / ml with a median of 1.5 hours (range 0.5–4 hours) after administration. After reaching the peak values, the LSD concentrations decreased according to first-order kinetics with a terminal half-life of 3.6 hours for up to 12 hours and then with a slower elimination with a terminal half-life of 8.9 hours. The effects of the administered dose of LSD lasted up to 12 hours and were closely correlated with circulating LSD concentrations over time, with no acute tolerance observed. Only 1% of the drug was eliminated unchanged in the urine, while 13% was eliminated as the main metabolite, 2-oxo-3-hydroxy-LSD (OH-LSD), within 24 hours. OH-LSD is produced by cytochrome P450 enzymes, although the specific enzymes involved are unknown and it does not appear to be known whether or not OH-LSD is pharmacologically active. The oral bioavailability of LSD has been roughly estimated to be approximately 71% using previous data on intravenous administration of LSD. The sample was divided equally between male and female subjects, and no significant sex differences in the pharmacokinetics of LSD were observed.
LSD is a chiral compound with two stereocenters on carbon atoms C-5 and C-8, so theoretically four different optical isomers of LSD could exist. LSD, also (+) - D- Called LSD, has the absolute configuration (5th R. , 8 R. ). The C-5 isomers of lysergamides do not exist in nature and are taken out during synthesis d- Lysergic acid not formed. Retrosynthetically, it could be analyzed that the C-5 stereocenter has the same configuration as the alpha carbon of the naturally occurring amino acid L-tryptophan, the precursor of all biosynthetic ergoline compounds.
However, LSD and iso-LSD, the two C-8 isomers, convert quickly in the presence of bases because the alpha proton is acidic and can be deprotonated and reprotonated. Non-psychoactive iso-LSD formed during synthesis can be separated by chromatography and isomerized to LSD.
Pure salts of LSD are triboluminescent and give off small white flashes of light when shaken in the dark. LSD is highly fluorescent and glows bluish-white under UV light.
LSD is a derivative of ergoline. It is usually synthesized by reacting diethylamine with an activated form of lysergic acid. Activation reagents include phosphoryl chloride and peptide coupling reagents. Lysergic acid made alkaline by hydrolysis of lysergamides such as ergotamine, a substance usually derived from the ergot fungi on agar plate; or theoretically possible, but impractical and unusual, from ergine (lysergic acid amide, LSA) extracted from the seeds. Lysergic acid can also be produced synthetically, which makes ergotamines superfluous.
A single dose of LSD can be anywhere from 40 to 500 micrograms - an amount roughly one tenth the mass of a grain of sand. Threshold effects can already be felt with 25 micrograms of LSD. The dosages of LSD are measured in micrograms (µg) or millionths of a gram. In comparison, the dosages of most recreational and medicinal drugs are measured in milligrams (mg) or thousandths of a gram. For example, an active dose of mescaline, approximately 0.2-0.5 g, has effects comparable to 100 µg or less of LSD.
In the mid-1960s, the main black market LSD manufacturer (Owsley Stanley) distributed acid at a standard concentration of 270 µg, while street samples in the 1970s contained 30 to 300 µg. In the 1980s the amount had dropped to 100 to 125 µg, in the 1990s to 20 to 80 µg and even more in the 2000s (decade).
Reactivity and degradation
"LSD", writes the chemist Alexander Shulgin, "is an unusually fragile molecule ... As a salt in water, cold and free of air and light, it is indefinitely stable."
LSD has two labile protons at the tertiary stereogenic C5 and C8 positions, making these centers susceptible to epimerization. The C8 proton is more labile due to the electron-withdrawing carboxamide bond, but the removal of the chiral proton at the C5 position (which was once an alpha proton of the parent tryptophan) is supported by the inductive nitrogen and pi-electron delocalization the indole ring.
LSD also has enamine-type reactivity because of the electron-donating effects of the indole ring. For this reason, chlorine destroys LSD molecules on contact. Although chlorinated tap water contains only a small amount of chlorine, the small amount of compound typical of an LSD solution is likely to be eliminated when dissolved in tap water. The double bond between the 8-position and the aromatic ring, which is conjugated with the indole ring, is susceptible to nucleophilic attack by water or alcohol, especially in the presence of UV or other types of light. LSD often converts to "Lumi-LSD", which is inactive in humans.
A controlled study was conducted to determine the stability of LSD in pooled urine samples. LSD concentrations in urine samples were monitored over time at different temperatures, in different types of storage containers, at different exposures to different wavelengths of light, and at different pH levels. These studies showed no significant loss in LSD concentration at 25 ° C for up to four weeks. After four weeks of incubation, a 30% loss in LSD concentration at 37 ° C and up to 40% at 45 ° C was observed. Urine fortified with LSD stored in amber glass or opaque polyethylene containers did not show a change in concentration under any light conditions. The stability of LSD in transparent containers under light was dependent on the distance between the light source and the samples, the wavelength of the light, the exposure time and the intensity of the light. After prolonged exposure to heat under alkaline pH conditions, 10 to 15% of the starting LSD epimerized to Iso-LSD. Under acidic conditions, less than 5% of the LSD was converted to iso-LSD. It has also been shown that trace amounts of metal ions in buffer or urine can catalyze the breakdown of LSD and that this process can be avoided by adding EDTA.
LSD can be quantified in urine, plasma, or serum as part of a substance abuse testing program to confirm a diagnosis of poisoning in hospital victims, or in whole blood to aid in a forensic investigation of traffic or other criminal injury or sudden death. Both the parent drug and its main metabolite are unstable in biofluids when exposed to light, heat or alkaline conditions. Therefore, the samples are protected from light, stored at the lowest possible temperature and quickly analyzed to minimize losses.
The apparent plasma half-life of LSD is estimated to be around 5.1 hours, with peak plasma concentrations occurring 3 hours after administration.
LSD can be detected with an Ehrlich reagent and a Hofmann reagent.
- Albert Hofmann on his first experiences with LSD
LSD was first synthesized on November 16, 1938 by Swiss chemist Albert Hofmann at Sandoz Laboratories in Basel, Switzerland as part of a major search research program for medically useful ergot alkaloid derivatives. The psychedelic properties of LSD were discovered 5 years later when Hofmann himself accidentally ingested an unknown amount of the chemical. The first intentional ingestion of LSD was on April 19, 1943, when Hofmann took 250 µg of LSD. He said this would be a threshold dose based on dosages of other ergot alkaloids. Hofmann found that the effects were much stronger than expected. Sandoz Laboratories introduced LSD as a psychiatric drug in 1947 and marketed LSD as a psychiatric panacea. They called it a "cure for everything from schizophrenia to criminal behavior to" sexual perversions "and alcoholism." The abbreviation "LSD" comes from the German "Lysergic acid diethylamide".
Starting in the 1950s, the US Central Intelligence Agency (CIA) started a research program code called Project MKUltra. The CIA introduced LSD in the United States, bought the entire global offering for $ 240,000, and distributed the LSD to American hospitals, clinics, prisons, and research centers through CIA front organizations. Experiments included administering LSD to CIA employees, military personnel, doctors, other government agents, prostitutes, mentally ill patients, and members of the general public to study their reactions, usually without the subjects' knowledge. The project was revealed in the 1975 report of the US Congressional Rockefeller Commission.
In 1963 the Sandoz patents for LSD expired. Several personalities, including Aldous Huxley, Timothy Leary and Al Hubbard, advocated the use of LSD. LSD became a central part of the counterculture of the 1960s. In the early 1960s, the use of LSD and other hallucinogens was advocated by new consciousness advocates such as Leary, Huxley, Alan Watts, and Arthur Koestler, and according to LR Veysey, they profoundly influenced the thinking of the new generation of teenagers.
On October 24, 1968, possession of LSD was made illegal in the United States. The last FDA-approved study of LSD in patients ended in 1980, while a study was conducted in healthy volunteers in the late 1980s. The legally approved and regulated psychiatric use of LSD continued in Switzerland until 1993.
In November 2020, Oregon became the first US state to decriminalize possession of small amounts of LSD after voters approved Election 110.
Society and culture
By the mid-1960s the youth had countercultures in California, especially San Francisco, resumed the use of hallucinogenic drugs, with Owsley Stanley's first major underground LSD factory being established. Beginning in 1964, the Merry Pranksters, a casual group that developed around writer Ken Kesey, sponsored the Acid Tests, a series of events primarily held in or near San Francisco that encouraged the uptake of LSD (by Stanley) accompanied, accompanied by light shows. Film projection and discordant, improvised music known as psychedelic symphony . The Pranksters helped spread LSD use through their road trips across America in a psychedelically decorated converted school bus where the drug was distributed and key figures in the Beat movement met, as well as through publications about their activities such as Tom Wolfe's The Kool-Aid Electrical Acid Test (1968).
In January 1966, brothers Ron and Jay Thelin opened the Psychedelic Shop in San Francisco's Haight-Ashbury district. The Thelins opened the store to promote the safe use of LSD, which was still legal in California at the time. The Psychedelic Shop helped spread LSD in Haight and turned the neighborhood into the unofficial capital of hippie counterculture in the United States. Ron Thelin was also involved in organizing the Love Pageant rally, a protest in Golden Gate Park to protest California's October 1966 ban on LSD. During the rally, hundreds of participants took acid together. Although the Psychedelic Shop closed after just under a year and a half, its role in popularizing LSD was considerable.
At around the same time, a similar and related link between LSD use in the creative arts developed in London. A key figure in this phenomenon in Britain was British academic Michael Hollingshead, who first tried LSD in America in 1961 as Executive Secretary of the Institute for British-American Cultural Exchange. After receiving a large amount of pure Sandoz LSD (which was still legal at the time) and experiencing his first "trip", Hollingshead contacted Aldous Huxley, who suggested that he contact Harvard academic Timothy Leary , and for the next few years, Hollingshead, along with Leary and Richard Alpert, played an important role in their famous LSD research in Millbrook before moving to New York City, where he conducted his own LSD experiments. In 1965 Hollingshead returned to the UK and founded the World Psychedelic Center in Chelsea, London.
Music and art
In both music and art, the influence of LSD was increased thanks to the bands that took part in the Acid Tests and related events, including the Grateful Dead, Jefferson Airplane and Big Brother and the Holding Company, and by The Invention Poster and album art by artists from San Francisco such as Rick Griffin, Victor Moscoso, Bonnie MacLean, Stanley Mouse and Alton Kelley, and Wes Wilson created the visual experience of an LSD journey. LSD had a strong influence on the Grateful Dead and the deadhead culture.
The many famous personalities in Britain who Michael Hollingshead reportedly introduced to LSD include artist and Hipgnosis founder Storm Thorgerson, as well as musicians Donovan, Keith Richards, Paul McCartney, John Lennon and George Harrison. Although establishment concerns about the new drug led to its being declared an illegal drug by the Home Secretary in 1966, LSD soon found widespread use among the upper echelons of the UK art and music scene, including members of the Beatles, the Rolling Stones . The Moody Blues, the Small Faces, Pink Floyd, Jimi Hendrix and others and the products of these experiences were soon used by singles like the "Itchycoo Park" of Small Faces and LPs like the Beatles' Sgt. Pepper's Lonely Hearts Club Band and creams Disraeli Gears , which included music showing the obvious influence of the musicians' recent psychedelic excursions, and which was wrapped in elaborately designed album covers of colorful psychedelic artwork by artists such as Peter Blake, Martin, Sharp, Hapshash and the Colored Coat (Nigel Waymouth
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