WordNet

the 12th letter of the Roman alphabet (同)l

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エルエスディー(一時的な幻覚や精神分裂状を引き起こす薬剤)
lira(イタリアの貨幣単位リラ)

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/12/22 18:12:38」(JST)

Lysergic acid diethylamide (/daɪ eθəl ˈæmaɪd/ or /æmɪd/ or /eɪmaɪd/),^[5]^[6]^[7] abbreviated LSD or LSD-25, also known as lysergide (INN) and colloquially as acid, is a psychedelic drug of the ergoline family, well known for its psychological effects—which can include altered thinking processes, closed- and open-eye visuals, synesthesia, an altered sense of time, and spiritual experiences—as well as for its key role in 1960s counterculture. It is used mainly as an entheogen and recreational drug. LSD is non-addictive.^[8] However, acute adverse psychiatric reactions such as anxiety, paranoia, and delusions are possible.^[9]

LSD was first synthesized by Albert Hofmann in 1938 from ergotamine, a chemical derived by Arthur Stoll from ergot, a grain fungus that typically grows on rye. The short form "LSD" comes from its early code name LSD-25, which is an abbreviation for the German "Lysergsäure-diethylamid" followed by a sequential number.^[10]^[11] LSD is sensitive to oxygen, ultraviolet light, and chlorine,^[11] especially in solution, though its potency may last for years if it is stored away from light and moisture at low temperature. In pure form it is a colorless, odorless, tasteless solid.^[12] LSD is typically either swallowed (oral) or held under the tongue (sublingual), usually on a substrate such as absorbent blotter paper, a sugar cube, or gelatin. In its liquid form, it can also be administered by intramuscular or intravenous injection. Interestingly, unlike most other classes of illicit drugs and other groups of psychedelic drugs such as tryptamines and phenethylamines, when LSD is administered via intravenous injection the onset is not immediate, instead taking approximately 30 minutes before the effects are realized. LSD is very potent, with 20–30 µg (micrograms) being the threshold dose.^[13]

Hofmann discovered the psychedelic properties of LSD in 1943.^[14] It was introduced commercially in 1947 by Sandoz Laboratories under the trade-name Delysid as a drug with various psychiatric uses.^[15] In the 1950s, officials at the U.S. Central Intelligence Agency (CIA) thought the drug might be applicable to mind control and chemical warfare; the agency's MKULTRA research program propagated the drug among young servicemen and students. The subsequent recreational use of the drug by youth culture in the Western world during the 1960s led to a political firestorm that resulted in its prohibition.^[16]

1 Effects
- 1.1 Physical
- 1.2 Psychological
- 1.3 Sensory
2 Uses
- 2.1 Medical
- 2.2 Recreational and spiritual
- 2.3 Entheogen
3 Adverse effects
- 3.1 Mental disorders
- 3.2 Suggestibility
- 3.3 Psychosis
- 3.4 Flashbacks and HPPD
- 3.5 Uterine contractions
- 3.6 Genetic
- 3.7 Addiction and tolerance
4 Overdose
5 Pharmacology
- 5.1 Pharmacodynamics
- 5.2 Pharmacokinetics
6 Physical and chemical properties
- 6.1 Synthesis
- 6.2 Dosage
- 6.3 Reactivity and degradation
- 6.4 Detection in body fluids
7 History
8 Society and culture
- 8.1 Legal status
  - 8.1.1 Australia
  - 8.1.2 Canada
  - 8.1.3 United Kingdom
  - 8.1.4 United States
- 8.2 Economics
  - 8.2.1 Production
    - 8.2.1.1 Forms
    - 8.2.1.2 Modern distribution
    - 8.2.1.3 Mimics
9 Research
- 9.1 Therapeutic use
  - 9.1.1 Psychedelic therapy
  - 9.1.2 End-of-life anxiety
  - 9.1.3 Alcoholism treatment
- 9.2 Pain management
- 9.3 Cluster headaches
- 9.4 Enhancing performance
10 See also
11 References
12 Further reading
13 External links

Effects

Physical

Notable physical effects of LSD and their locales of occurrence.

LSD can cause pupil dilation, reduced appetite, and wakefulness. Other physical reactions to LSD are highly variable and nonspecific, some of which may be secondary to the psychological effects of LSD. Among the reported symptoms are numbness, weakness, nausea, hypothermia or hyperthermia, elevated blood sugar, goose bumps, heart rate increase, jaw clenching, perspiration, saliva production, mucus production, sleeplessness, hyperreflexia, and tremors.^{[medical citation needed]}

Psychological

LSD's psychological effects (colloquially called a "trip") vary greatly between persons and places. If the user is in a hostile or otherwise unsettling environment, or is not mentally prepared for the powerful distortions in perception and thought that the drug causes, effects are more likely to be unpleasant than if he or she is in a comfortable environment and has a relaxed, balanced and open mindset.^{[medical citation needed]}

An LSD trip can have long-term psychological or emotional effects; some users^[who?] report the LSD experience as causing significant long term changes in their personality and life perspective.^[17] Widely different effects emerge based on what Timothy Leary called set and setting; the "set" being the general mindset of the user, and the "setting" being the physical and social environment in which the drug's effects are experienced.^{[citation needed]} Some psychological effects may include a sense that one's thoughts are spiraling into themselves and a loss of a sense of identity or the ego (known as "ego death").^{[medical citation needed]} Many users experience a dissolution between themselves and the "outside world".^[18] This unitive quality may play a role in the spiritual and religious aspects of LSD. The drug sometimes leads to disintegration or restructuring of the user's historical personality and creates a mental state that some users^{[weasel words]} report allows them to have more choice regarding the nature of their own personality.^{[medical citation needed]}

Sensory

Some sensory effects may include an experience of radiant colors, objects and surfaces appearing to ripple or "breathe", colored patterns behind the closed eyelids (eidetic imagery), an altered sense of time (time seems to be stretching, repeating itself, changing speed or stopping), crawling geometric patterns overlaying walls and other objects, and morphing objects.^[18] Some users, including Albert Hofmann, report a strong metallic taste for the duration of the effects.^[19]

LSD causes an animated sensory experience of senses, emotions, memories, time, and awareness for 6 to 14 hours, depending on dosage and tolerance. Generally beginning within 30 to 90 minutes after ingestion, the user may experience anything from subtle changes in perception to overwhelming cognitive shifts. Changes in auditory and visual perception are typical.^[18]^[20] Visual effects include the illusion of movement of static surfaces ("walls breathing"), after image-like trails of moving objects ("tracers"), the appearance of moving colored geometric patterns (especially with closed eyes), an intensification of colors and brightness ("sparkling"), new textures on objects, blurred vision, and shape suggestibility. Users commonly report^{[weasel words]} that the inanimate world appears to animate in an inexplicable way; for instance, objects that are static in three dimensions can seem to be moving relative to one or more additional spatial dimensions.^[21] Many of the basic visual effects resemble the phosphenes seen after applying pressure to the eye and have also been studied under the name "form constants". The auditory effects of LSD may include echo-like distortions of sounds, changes in ability to discern concurrent auditory stimuli, and a general intensification of the experience of music. Higher doses often cause intense and fundamental distortions of sensory perception such as synaesthesia, the experience of additional spatial or temporal dimensions, and temporary dissociation.^{[medical citation needed]}

Uses

Medical

LSD currently has no recognized medical use, however further research into LSD's potential as a treatment for addiction is warranted.^[22]

Recreational and spiritual

Pink elephant blotters containing LSD

LSD is commonly used as a recreational drug for its psychedelic effects.^[23]

Entheogen

LSD is considered an entheogen because it can catalyze intense spiritual experiences, during which users may feel they have come into contact with a greater spiritual or cosmic order. Users claim to experience lucid sensations where they have "out of body" experiences. In 1966, Timothy Leary established the League for Spiritual Discovery with LSD as its sacrament.^[24]^[25] Stanislav Grof has written that religious and mystical experiences observed during LSD sessions appear to be phenomenologically indistinguishable from similar descriptions in the sacred scriptures of the great religions of the world and the secret mystical texts of ancient civilizations.^[26]

Adverse effects

In a 2011 survey of 292 clinical experts in Scotland, LSD ranked 4th lowest in personal harm and 6th lowest in social harm out of 19 common recreational drugs.^[27]

Long-term effects include "flashbacks" and a syndrome of long-term perceptual changes that are experienced as distressing.^[28]^[29]

Mental disorders

LSD may trigger panic attacks or feelings of extreme anxiety, colloquially referred to as a "bad trip". There is evidence that people with severe mental illnesses like schizophrenia have a higher likelihood of experiencing adverse effects from taking LSD (see psychosis for further details).^[30]^{[unreliable medical source]} No real prolonged effects have been proven, although PTSD has been reported after some intensely distressful LSD experiences.^{[medical citation needed]}

Suggestibility

While publicly available documents indicate that the CIA and Department of Defense have discontinued research into the use of LSD as a means of mind control,^[31] research from the 1960s suggests there exists evidence that both mentally ill and healthy people are more suggestible while under its influence.^[32]^[33]^{[non-primary source needed]}

Psychosis

Historical data suggests that there has been the occasional incidence of long-term LSD induced psychosis in people who appeared to be healthy prior to taking the drug.^[34]

Flashbacks and HPPD

"Flashbacks" are a reported psychological phenomenon in which an individual experiences an episode of some of LSD's subjective effects after the drug has worn off, "persisting for months or years after hallucinogen use".^[35] Several studies have tried to determine how likely a user of LSD, not suffering from known psychiatric conditions, is to experience flashbacks. The larger studies include Blumenfeld's in 1971^[35]^[36]^[37]^[38]^[39] and Naditch and Fenwick's in 1977,^[40]^[41]^[42]^[43]^[44] which arrived at figures of 20%^[36] and 28%,^[40] respectively.^[28]^[45]^[46]

Hallucinogen Persisting Perception Disorder (HPPD) describes a post-LSD exposure syndrome in which LSD-like visual changes are not temporary and brief, as they are in flashbacks, but instead are persistent, and cause clinically significant impairment or distress. The syndrome is a DSM-IV diagnosis. Several scientific journal articles have described the disorder.^[47] HPPD differs from flashbacks in that it is persistent and apparently entirely visual (although mood and anxiety disorders are sometimes diagnosed in the same individuals). A recent review suggests that HPPD (as defined in the DSM-IV) is uncommon and affects a distinctly vulnerable subpopulation of users.^[48]^[49]

Uterine contractions

Early pharmacological testing by Sandoz in laboratory animals showed that LSD can stimulate uterine contractions, with efficacy comparable to ergobasine, the active uterotonic component of the ergot fungus.^{[medical citation needed]}

Genetic

The mutagenic potential of LSD is unclear. Overall, the evidence seems to point to limited or no effect at commonly used doses.^[50]

Addiction and tolerance

LSD is not considered addictive by the medical community^[8] and experimental evidence has demonstrated that positive reinforcement, which is a necessary condition for addiction, does not arise when it is used by humans or other animals.^[2] Tolerance to LSD-25 builds up over consistent use^[51] and cross-tolerance has been demonstrated between LSD, mescaline^[52] and psilocybin.^[53] This tolerance diminishes a few days after cessation of use and is probably caused by downregulation of 5-HT_2A receptors in the brain.^[54]^[55]

Overdose

Reassurance in a calm, safe environment is beneficial. Agitation can be safely addressed with benzodiazepines such as lorazepam or diazepam. Neuroleptics such as haloperidol should be avoided for they may have adverse effects. LSD is rapidly absorbed, so activated charcoal and emptying of the stomach will be of little benefit, unless done within 30–60 minutes of ingesting vast amounts of LSD. Sedation or physical restraint is rarely required, and excessive restraint may cause complications such as hyperthermia (over-heating) or rhabdomyolysis.^[56]

Massive doses require supportive care, which may include endotracheal intubation or respiratory support. Overdose has been recorded at 1,000 to 7,000μg per 100ml & 2.1 to 26 ng per ml in serum concentrations of the tartrate salt form. High blood pressure, tachycardia (rapid heart-beat) and hyperthermia, if present, should be treated symptomatically. Treat low blood pressure initially with fluids and then with pressors if necessary. Intravenous administration of anticoagulants, vasodilators, and sympatholytics may be useful with massive doses.^[57]

Pharmacology

Pharmacodynamics

Binding affinities of LSD for various receptors. The lower the dissociation constant (K_i), the more strongly LSD binds to that receptor (i.e. with higher affinity). The horizontal line represents an approximate value for human plasma concentrations of LSD, and hence, receptor affinities that are above the line are unlikely to be involved in LSD's effect. Data averaged from data from the K_i Database

LSD affects a large number of the G protein-coupled receptors, including all dopamine receptor subtypes, and all adrenoreceptor subtypes, as well as many others.^{[citation needed]} Most serotonergic psychedelics are not significantly dopaminergic, and LSD is therefore rather unique in this regard. LSD's agonism of D₂ receptors contributes to its psychoactive effects.^[58]^[59] LSD binds to most serotonin receptor subtypes except for 5-HT₃ and 5-HT₄. However, most of these receptors are affected at too low affinity to be sufficiently activated by the brain concentration of approximately 10–20 nM.^[60] In humans, recreational doses of LSD can affect 5-HT_1A (K_i=1.1nM), 5-HT_2A (K_i=2.9nM), 5-HT_2B (K_i=4.9nM), 5-HT_2C (K_i=23nM), 5-HT_5A (K_i=9nM [in cloned rat tissues]), and 5-HT₆ receptors (K_i=2.3nM).^[3]^[61] 5-HT_5B receptors, which are not present in humans, also have a high affinity for LSD.^[62] The psychedelic effects of LSD are attributed to cross-activation of 5-HT_2A receptor heteromers.^[63] Many but not all 5-HT_2A agonists are psychedelics and 5-HT_2A antagonists block the psychedelic activity of LSD. LSD exhibits functional selectivity at the 5-HT_2A and 5HT_2C receptors in that it activates the signal transduction enzyme phospholipase A2 instead of activating the enzyme phospholipase C as the endogenous ligand serotonin does.^[64] Exactly how LSD produces its effects is unknown, but it is thought that it works by increasing glutamate release in the cerebral cortex^[60] and therefore excitation in this area, specifically in layers IV and V.^[65] LSD, like many other drugs, has been shown to activate DARPP-32-related pathways.^[66]

LSD enhances dopamine D2R protomer recognition and signaling of D2–5-HT2A receptor complexes. This mechanism may contribute to the psychotic actions of LSD.^[67]

Pharmacokinetics

LSD's effects normally last from 6–12 hours depending on dosage, tolerance, body weight and age.^[11] The Sandoz prospectus for "Delysid" warned: "intermittent disturbances of affect may occasionally persist for several days."^[10] Contrary to early reports and common belief, LSD effects do not last longer than the amount of time significant levels of the drug are present in the blood. Aghajanian and Bing (1964) found LSD had an elimination half-life of only 175 minutes.^[3] However, using more accurate techniques, Papac and Foltz (1990) reported that 1 µg/kg oral LSD given to a single male volunteer had an apparent plasma half-life of 5.1 hours, with a peak plasma concentration of 5 ng/mL at 3 hours post-dose.^[4]

Physical and chemical properties

The four possible stereoisomers of LSD. Only (+)-LSD is psychoactive.

LSD is a chiral compound with two stereocenters at the carbon atoms C-5 and C-8, so that theoretically four different optical isomers of LSD could exist. LSD, also called (+)-D-LSD, has the absolute configuration (5R,8R). The C-5 isomers of lysergamides do not exist in nature and are not formed during the synthesis from D-lysergic acid. Retrosynthetically, the C-5 stereocenter could be analysed as having the same configuration of the alpha carbon of the naturally occurring amino acid L-tryptophan, the precursor to all biosynthetic ergoline compounds.

However, LSD and iso-LSD, the two C-8 isomers, rapidly interconvert in the presence of bases, as the alpha proton is acidic and can be deprotonated and reprotonated. Non-psychoactive iso-LSD which has formed during the synthesis can be separated by chromatography and can be isomerized to LSD.

Pure salts of LSD are triboluminescent, emitting small flashes of white light when shaken in the dark.^[11] LSD is strongly fluorescent and will glow bluish-white under UV light.

Synthesis

LSD is an ergoline derivative. It is commonly synthesised by reacting diethylamine with an activated form of lysergic acid. Activating reagents include phosphoryl chloride^[68] and peptide coupling reagents.^[69] Lysergic acid is made by alkaline hydrolysis of lysergamides like ergotamine, a substance usually derived from the ergot fungus on agar plate, or theoretically possible, but impractical and uncommon from ergine (lysergic acid amide, LSA) extracted from morning glory seeds.^[70] Lysergic acid can also be produced synthetically, eliminating the need for ergotamines.^[71]^[72]

Dosage

White on White blotters (WoW)

A single dose of LSD may be between 40 and 500 micrograms—an amount roughly equal to one-tenth the mass of a grain of sand. Threshold effects can be felt with as little as 25 micrograms of LSD.^[13]^[73] Dosages of LSD are measured in micrograms (µg), or millionths of a gram. By comparison, dosages of most drugs, both recreational and medicinal, are measured in milligrams (mg), or thousandths of a gram. For example, an active dose of mescaline, roughly 0.2 to 0.5 g, has effects comparable to 100 µg or less of LSD.^[10]

In the mid-1960s, the most important black market LSD manufacturer (Owsley Stanley) distributed acid at a standard concentration of 270 µg,^[74] while street samples of the 1970s contained 30 to 300 µg. By the 1980s, the amount had reduced to between 100 and 125 µg, dropping more in the 1990s to the 20–80 µg range,^[75] and even more in the 2000s (decade).^[74] ^[76]

Reactivity and degradation

"LSD," writes the chemist Alexander Shulgin, "is an unusually fragile molecule… As a salt, in water, cold, and free from air and light exposure, it is stable indefinitely."^[11]

LSD has two labile protons at the tertiary stereogenic C5 and C8 positions, rendering these centres prone to epimerisation. The C8 proton is more labile due to the electron-withdrawing carboxamide attachment, but removal of the chiral proton at the C5 position (which was once also an alpha proton of the parent molecule tryptophan) is assisted by the inductively withdrawing nitrogen and pi electron delocalisation with the indole ring.^{[citation needed]}

LSD also has enamine-type reactivity because of the electron-donating effects of the indole ring. Because of this, chlorine destroys LSD molecules on contact; even though chlorinated tap water contains only a slight amount of chlorine, the small quantity of compound typical to an LSD solution will likely be eliminated when dissolved in tap water.^[11] The double bond between the 8-position and the aromatic ring, being conjugated with the indole ring, is susceptible to nucleophilic attacks by water or alcohol, especially in the presence of light. LSD often converts to "lumi-LSD", which is inactive in human beings.^[11]

A controlled study was undertaken to determine the stability of LSD in pooled urine samples.^[77] The concentrations of LSD in urine samples were followed over time at various temperatures, in different types of storage containers, at various exposures to different wavelengths of light, and at varying pH values. These studies demonstrated 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 a 40% at 45 °C were observed. Urine fortified with LSD and stored in amber glass or nontransparent polyethylene containers showed no change in concentration under any light conditions. Stability of LSD in transparent containers under light was dependent on the distance between the light source and the samples, the wavelength of light, exposure time, and the intensity of light. After prolonged exposure to heat in alkaline pH conditions, 10 to 15% of the parent LSD epimerized to iso-LSD. Under acidic conditions, less than 5% of the LSD was converted to iso-LSD. It was also demonstrated that trace amounts of metal ions in buffer or urine could catalyze the decomposition of LSD and that this process can be avoided by the addition of EDTA.

Detection in body fluids

LSD may be quantified in urine as part of a drug abuse testing program, in plasma or serum to confirm a diagnosis of poisoning in hospitalized victims or in whole blood to assist in a forensic investigation of a traffic or other criminal violation or a case of sudden death. Both the parent drug and its major metabolite are unstable in biofluids when exposed to light, heat or alkaline conditions and therefore specimens are protected from light, stored at the lowest possible temperature and analyzed quickly to minimize losses.^[78]

History

"... affected by a remarkable restlessness, combined with a slight dizziness. At home I lay down and sank into a not unpleasant intoxicated-like condition, characterized by an extremely stimulated imagination. In a dreamlike state, with eyes closed (I found the daylight to be unpleasantly glaring), I perceived an uninterrupted stream of fantastic pictures, extraordinary shapes with intense, kaleidoscopic play of colors. After some two hours this condition faded away."

Albert Hofmann, on his first experience with LSD^[79]

LSD was first synthesized on November 16, 1938^[80] by Swiss chemist Albert Hofmann at the Sandoz Laboratories in Basel, Switzerland as part of a large research program searching for medically useful ergot alkaloid derivatives. LSD's psychedelic properties were discovered 5 years later when Hofmann himself accidentally ingested an unknown quantity of the chemical.^[81] The first intentional ingestion of LSD occurred on April 19, 1943,^[82] when Hofmann ingested 250 µg of LSD. He said this would be a threshold dose based on the dosages of other ergot alkaloids. Hofmann found the effects to be much stronger than he anticipated.^[83] Sandoz Laboratories introduced LSD as a psychiatric drug in 1947.^[84]

Albert Hofmann in 2006

Beginning in the 1950s, the US Central Intelligence Agency began a research program code named Project MKULTRA. Experiments included administering LSD to CIA employees, military personnel, doctors, other government agents, prostitutes, mentally ill patients, and members of the general public in order to study their reactions, usually without the subjects' knowledge. The project was revealed in the US congressional Rockefeller Commission report in 1975.

In 1963, the Sandoz patents expired on LSD.^[75] Several figures, including Aldous Huxley, Timothy Leary, and Al Hubbard, began to advocate the consumption of LSD. LSD became central to the counterculture of the 1960s.^[85] On October 24, 1968, possession of LSD was made illegal in the United States.^[86] The last FDA approved study of LSD in patients ended in 1980, while a study in healthy volunteers was made in the late 1980s. Legally approved and regulated psychiatric use of LSD continued in Switzerland until 1993.^[87]

Society and culture

Legal status

The United Nations Convention on Psychotropic Substances (adopted in 1971) requires its parties to prohibit LSD. Hence, it is illegal in all parties to the convention, which includes the United States, Australia, New Zealand, and most of Europe. However, enforcement of extant laws varies from country to country. Medical and scientific research with LSD in humans is permitted under the 1971 UN Convention.^[88]

Australia

LSD is a schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015).^[89] A schedule 9 drug is outlined in the Poisons Act 1964 as "Substances which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of the CEO." ^[90]

Under the Misuse of Drugs Act 1981 0.004g of Lysergic Acid Diethylamide (LSD) is the amount required determining court of trial, 0.01g is determined for purposes of drug trafficking.^[91]

Canada

In Canada, LSD is a controlled substance under Schedule III of the Controlled Drugs and Substances Act.^[92] Every person who seeks to obtain the substance, without disclosing authorization to obtain such substances 30 days before obtaining another prescription from a practitioner, is guilty of an indictable offense and liable to imprisonment for a term not exceeding 3 years. Possession for purpose of trafficking is an indictable offense punishable by imprisonment for 10 years.

United Kingdom

In the United Kingdom, LSD is a Schedule 1 Class 'A' drug. This means it has no recognised legitimate uses and possession of the drug without a license is punishable with 7 years' imprisonment and/or an unlimited fine, and trafficking is punishable with life imprisonment and an unlimited fine (see main article on drug punishments Misuse of Drugs Act 1971).

In 2000, after consultation with members of the Royal College of Psychiatrists' Faculty of Substance Misuse, the UK Police Foundation issued the Runciman Report which recommended "the transfer of LSD from Class A to Class B".^[93]

In November 2009, the UK Transform Drug Policy Foundation released in the House of Commons a guidebook to the legal regulation of drugs, After the War on Drugs: Blueprint for Regulation, which details options for regulated distribution and sale of LSD and other psychedelics.^[94]

United States

LSD is Schedule I in the United States, according to the Controlled Substances Act of 1970.^[95] This means LSD is illegal to manufacture, buy, possess, process, or distribute without a DEA license. By classifying LSD as a Schedule I substance, the Drug Enforcement Administration holds that LSD meets the following three criteria: it is deemed to have a high potential for abuse; it has no legitimate medical use in treatment; and there is a lack of accepted safety for its use under medical supervision. There are no documented deaths from chemical toxicity; most LSD deaths are a result of behavioral toxicity.^[96]

There can also be substantial discrepancies between the amount of chemical LSD that one possesses and the amount of possession with which one can be charged in the U.S. This is because LSD is almost always present in a medium (e.g. blotter or neutral liquid), and the amount that can be considered with respect to sentencing is the total mass of the drug and its medium. This discrepancy was the subject of 1995 United States Supreme Court case, Neal v. U.S.^[97]

Lysergic acid and lysergic acid amide, LSD precursors, are both classified in Schedule III of the Controlled Substances Act. Ergotamine tartrate, a precursor to lysergic acid, is regulated under the Chemical Diversion and Trafficking Act.

Economics

Production

Glassware seized by the DEA

An active dose of LSD is very minute, allowing a large number of doses to be synthesized from a comparatively small amount of raw material. Twenty five kilograms of precursor ergotamine tartrate can produce 5–6 kg of pure crystalline LSD; this corresponds to 100 million doses. Because the masses involved are so small, concealing and transporting illicit LSD is much easier than smuggling other illegal drugs like cocaine or cannabis.^[98]

Manufacturing LSD requires laboratory equipment and experience in the field of organic chemistry. It takes two to three days to produce 30 to 100 grams of pure compound. It is believed that LSD is not usually produced in large quantities, but rather in a series of small batches. This technique minimizes the loss of precursor chemicals in case a step does not work as expected.^[98]^{[dead link]}

Forms

Five doses of LSD, often called a "five strip"

LSD is produced in crystalline form and then mixed with excipients or redissolved for production in ingestible forms. Liquid solution is either distributed in small vials or, more commonly, sprayed onto or soaked into a distribution medium. Historically, LSD solutions were first sold on sugar cubes, but practical considerations forced a change to tablet form. Appearing in 1968 as an orange tablet measuring about 6 mm across, "Orange Sunshine" acid was the first largely available form of LSD after its possession was made illegal. Tim Scully, a prominent chemist, made some of these tablets, but said that most "Sunshine" in the USA came by way of Ronald Stark, who imported approximately thirty-five million doses from Europe.^[99]

Over a period of time, tablet dimensions, weight, shape and concentration of LSD evolved from large (4.5–8.1 mm diameter), heavyweight (≥150 mg), round, high concentration (90–350 µg/tab) dosage units to small (2.0–3.5 mm diameter) lightweight (as low as 4.7 mg/tab), variously shaped, lower concentration (12–85 µg/tab, average range 30–40 µg/tab) dosage units. LSD tablet shapes have included cylinders, cones, stars, spacecraft, and heart shapes. The smallest tablets became known as "Microdots".^[100]

After tablets came "computer acid" or "blotter paper LSD", typically made by dipping a preprinted sheet of blotting paper into an LSD/water/alcohol solution.^[99]^[100] More than 200 types of LSD tablets have been encountered since 1969 and more than 350 blotter paper designs have been observed since 1975.^[100] About the same time as blotter paper LSD came "Windowpane" (AKA "Clearlight"), which contained LSD inside a thin gelatin square a quarter of an inch (6 mm) across.^[99] LSD has been sold under a wide variety of often short-lived and regionally restricted street names including Acid, Trips, Uncle Sid, Blotter, Lucy, Alice and doses, as well as names that reflect the designs on the sheets of blotter paper.^[101]^[102] Authorities have encountered the drug in other forms—including powder or crystal, and capsule.^[103]

Modern distribution

LSD manufacturers and traffickers in the United States can be categorized into two groups: A few large-scale producers, and an equally limited number of small, clandestine chemists, consisting of independent producers who, operating on a comparatively limited scale, can be found throughout the country.^[104] As a group, independent producers are of less concern to the Drug Enforcement Administration than the larger groups, as their product reaches only local markets.^[105]

Mimics

LSD blotter acid mimic actually containing DOC

Different blotters which could possibly be mimics

Since 2005, law enforcement in the United States and elsewhere has seized several chemicals and combinations of chemicals in blotter paper which were sold as LSD mimics, including DOB,^[106]^[107] a mixture of DOC and DOI,^[108] 25I-NBOMe,^[109] and a mixture of DOC and DOB.^[110] Street users of LSD are often under the impression that blotter paper which is actively hallucinogenic can only be LSD because that is the only chemical with low enough doses to fit on a small square of blotter paper. While it is true that LSD requires lower doses than most other hallucinogens, blotter paper is capable of absorbing a much larger amount of material. The DEA performed a chromatographic analysis of blotter paper containing 2C-C which showed that the paper contained a much greater concentration of the active chemical than typical LSD doses, although the exact quantity was not determined.^[111] Blotter LSD mimics can have relatively small dose squares; a sample of blotter paper containing DOC seized by Concord, California police had dose markings approximately 6 mm apart.^[112]

Research

Currently, a number of organizations—including the Beckley Foundation, MAPS, Heffter Research Institute and the Albert Hofmann Foundation—exist to fund, encourage and coordinate research into the medicinal and spiritual uses of LSD and related psychedelics.^[113] New clinical LSD experiments in humans started in 2009 for the first time in 35 years.^[114]

In 2001 the United States Drug Enforcement Administration stated that LSD "produces no aphrodisiac effects, does not increase creativity, has no lasting positive effect in treating alcoholics or criminals, does not produce a 'model psychosis', and does not generate immediate personality change."^[115] More recently experimental uses of LSD have included the treatment of alcoholism^[116] and pain and cluster headache relief.^[117] It has also been used for spiritual purposes, and for its putative effects in increasing creativity.^[118]

Therapeutic use

Psychedelic therapy

In the 1950s and 1960s LSD was used in psychiatry to enhance psychotherapy known as psychedelic therapy. Some psychiatrists^[who?] believed LSD was especially useful at helping patients to "unblock" repressed subconscious material through other psychotherapeutic methods,^[119] and also for treating alcoholism.^[120]^[121] One study concluded, "The root of the therapeutic value of the LSD experience is its potential for producing self-acceptance and self-surrender,"^[122] presumably by forcing the user to face issues and problems in that individual's psyche.

Two recent reviews concluded that conclusions drawn from most of these early trials are unreliable due to serious methodological flaws. These include the absence of adequate control groups, lack of followup, and vague criteria for therapeutic outcome. In many cases studies failed to convincingly demonstrate whether the drug or the therapeutic interaction was responsible for any beneficial effects.^[123]^[124]

End-of-life anxiety

Since 2008 there has been ongoing research into using LSD to alleviate anxiety for terminally ill cancer patients coping with their impending deaths.^[125]^[126]

Alcoholism treatment

A 2012 meta-analysis of six randomized controlled trials found evidence that a single dose of LSD in conjunction with various alcoholism treatment programs was associated with a decrease in alcohol abuse, lasting for several months, but no effect was seen at one year. Adverse events included seizure, moderate confusion and agitation, nausea, vomiting, and acting in a bizarre fashion.^[127]

Pain management

LSD was studied in the 1960s by Eric Kast for pain management as an analgesic for serious and chronic suffer caused by cancer or other major trauma.^[128]

Cluster headaches

LSD has been used as a treatment for cluster headaches with positive results in some small studies.^[117]^[129]

Enhancing performance

In the 1950s and 1960s, psychiatrists like Oscar Janiger explored the potential effect of LSD on creativity. Experimental studies attempted to measure the effect of LSD on creative activity and aesthetic appreciation.^[130]^[131]^[132]^[133] Seventy professional artists were asked to draw two pictures of a Hopi Indian kachina doll, one before ingesting LSD and one after.^[134]

There is anecdotal evidence indicating that micro dosing psychedelic drugs such as LSD can have positive effects as a mood and performance enhancer.^[135] The inventor of LSD, Albert Hofmann, was known to microdose in his old age and told a friend that microdosing was an under-researched area. But microdosing gained greater visibility when James Fadiman, a psychologist and researcher at Sofia University in Palo Alto, California, described it in his book "The Psychedelic Explorer's Guide" (Park Street Press, 2011).^[136]

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External links

Drug Profiles: LSD European Monitoring Centre for Drugs and Drug Addiction
LSD-25 at Erowid
The Lycaeum Archive: LSD
LSD entry in TiHKAL • info
InfoFacts – Hallucinogens NIDA
Scholarly bibliography on the histories of LSD use
LSD Returns-For Psychotherapeutics (Scientific American Magazine article)
U.S. National Library of Medicine: Drug Information Portal – Lysergic acid diethylamide
My LSD Trip: a non-cop, non-hippie report of the unvarnished facts, by Robert Gannon, Popular Science Magazine, December 1967.
WWW Psychedelic Bibliography, MAPS – large database of scientific publications on LSD and other psychedelics, fulltext PDFs

Documentaries

Hofmann's Potion a documentary on the origins of LSD
Power & Control LSD in The Sixties on YouTube, documentary film directed by Aron Ranen, 2006
Inside LSD National Geographic Channel, 2009

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. LSDおよび他の一般的な幻覚剤による中毒 intoxication from lsd and other common hallucinogens
2. 薬物乱用検査（DOA） testing for drugs of abuse doa
3. キノコ中毒の臨床症状および評価 clinical manifestations and evaluation of mushroom poisoning
4. 小児における急性発症性精神病の救急外来による評価 emergency department evaluation of acute onset psychosis in children
5. 合成カンナビノイド：急性中毒 synthetic cannabinoids acute intoxication

English Journal

Screening analysis for medicinal drugs and drugs of abuse in whole blood using ultra-performance liquid chromatography time-of-flight mass spectrometry (UPLC-TOF-MS)-Toxicological findings in cases of alleged sexual assault.

Birkler RI, Telving R, Ingemann-Hansen O, Charles AV, Johannsen M, Andreasen MF.SourceSection for Toxicology and Drug Analysis, Department of Forensic Medicine, Aarhus University, Brendstrupgaardsvej 100, DK-8200 Aarhus N, Denmark.
Forensic science international.Forensic Sci Int.2012 Oct 10;222(1-3):154-61. Epub 2012 Jul 6.
An ultra-performance liquid chromatography time-of-flight mass spectrometry (UPLC-TOF-MS) method for simultaneous screening of 46 medicinal drugs and drugs of abuse in whole blood was developed and validated. The method includes most of the commonly used and abused drugs such as amphetamines, cocain
PMID 22770621

Merits of combination cortical, subcortical, and cerebellar injections for the treatment of niemann-pick disease type a.

Bu J, Ashe KM, Bringas J, Marshall J, Dodge JC, Cabrera-Salazar MA, Forsayeth J, Schuchman EH, Bankiewicz KS, Cheng SH, Shihabuddin LS, Passini MA.SourceRare Diseases Division, Genzyme Corporation, Framingham, Massachusetts, USA.
Molecular therapy : the journal of the American Society of Gene Therapy.Mol Ther.2012 Oct;20(10):1893-901. doi: 10.1038/mt.2012.118. Epub 2012 Jul 24.
Niemann-Pick disease Type A (NPA) is a neuronopathic lysosomal storage disease (LSD) caused by the loss of acid sphingomyelinase (ASM). The goals of the current study are to ascertain the levels of human ASM that are efficacious in ASM knockout (ASMKO) mice, and determine whether these levels can be
PMID 22828503

Japanese Journal

遊星歯車式トルク感応型LSDの摩擦挙動に及ぼす粗さとコーティングの影響

安藤淳二,安藤寛之,齋藤秀幸 [他]
自動車技術会論文集 42(2), 379-384, 2011-03
NAID 40018772956

Reduced complexity optimum detector for block data transmission systems using Lattice Sphere Decoding technique

Albreem Mahmoud A. M.,Salleh M. F. M.,Babu SPK
IEICE Electronics Express 8(9), 644-649, 2011
… In this paper, a Lattice Sphere Decoding (LSD) technique is proposed for detection in block data transmission systems (BDTS). … Simulation results at 10dB channel SNR of BDTS with LSD using block size of 20 performs are near Hybrid Micro Genetic Algorithm (HMGA) and slightly inferior than the exhaustive search technique using the channels with spectral nulls. …
NAID 130000654749

Related Pictures

★リンクテーブル★

リンク元	「薬物濫用」「譫妄」「セロトニン症候群」「健忘」「濫用薬物」
関連記事	「LS」「L」

「薬物濫用」

Lysergic acid diethylamide
Systematic (IUPAC) name
	(6aR,9R)-N,N-diethyl-7-methyl-4,6,6a,7,8,9-hexahydroindolo-[4,3-fg]quinoline-9-carboxamide
Clinical data
Pregnancy; category	US: C (Risk not ruled out); ;
Legal status	AU: S9 (Prohibited); CA: Schedule III; DE: Anlage I; NZ: Class A; UK: Class A; US: Schedule I; UN: Psychotropic Schedule I;
Dependence; liability	Low
Addiction; liability	None
Routes of; administration	Oral, sublingual, intravenous, ocular, intramuscular
Pharmacokinetic data
Metabolism	Hepatic
Biological half-life	3–5 hours
Excretion	Renal
Identifiers
CAS Number	50-37-3
ATC code	None
PubChem	CID: 5761
IUPHAR/BPS	17
DrugBank	DB04829
ChemSpider	5558
UNII	8NA5SWF92O
ChEBI	CHEBI:6605
ChEMBL	CHEMBL263881
Synonyms	Acid, LSD, lysergide
Chemical data
Formula	C20H25N3O
Molecular mass	323.44 g·mol−1
	SMILES CCN(CC)C(=O)[C@H]1CN([C@@H]2Cc3c[nH]c4c3c(ccc4)C2=C1)C ;
	InChI InChI=1S/C20H25N3O/c1-4-23(5-2)20(24)14-9-16-15-7-6-8-17-19(15)13(11-21-17)10-18(16)22(3)12-14/h6-9,11,14,18,21H,4-5,10,12H2,1-3H3/t14-,18-/m1/s1 ; Key:VAYOSLLFUXYJDT-RDTXWAMCSA-N ;
Physical data
Melting point	80 to 85 °C (176 to 185 °F)
(verify)

　　[★]

英: drug abuse, substance abuse
同: 薬物乱用
関: 薬物依存、薬物嗜癖、物質乱用、物質依存症、薬物使用、接着剤吸引

薬物使用が身体に及ぼす効果

濫用 substance abuse：a pattern of abnormal substance use that leads to impairment of occupational, physical, or social functioning(BBS.73)
依存 substance dependence：ub stance abuse puls withdrawal symptoms, tolerance, or a pattern of repetitive use(BBS.73)
離脱 withdrawal：the development of physical or pschological symptoms after the reduction or cessation of intake of a substance(BBS.73)
耐性 tolerance：the need for increased amounts of the substance to achieve the same positive psychological effect(BBS.73)
交差耐性 cross-tolerance：the development of tolerance to one substance as the result of using another substance(BBS.73)

薬物

1. 中枢神経興奮薬(覚醒剤を含む) stimulants　　身体依存はないとされている

カフェイン caffeine
ニコチン nicotine
amphetamines　精神依存有り。身体依存無し

アンフェタミン amphetamine　精神依存有り。身体依存無し。耐性は連用で出現
デキストロアンフェタミン dextroamphetamine Dexedrine
メタンフェタミン methamphetamine Desoxyn speed ice ヒロポン　精神依存有り。身体依存無し。耐性は連用で出現　　←　以前、日本で多く使われた
メチルフェニデート methylphenidate Ritalin
methylene dioxymethamphetamine MDMA ecstasy

コカイン cocaine crack freebase　精神依存有り。身体依存無し　精神依存生じやすい。耐性発現殆ど無し　コカ

2. sedatives

alcohol　　精神依存有り。身体依存有り。
barbiturates
benzodiazepines

⇔flumazenil Mazicon Romazicon

3. opioids

morphine　精神依存・身体依存有り　けし
heroin　精神依存・身体依存が強い。耐性発現早い。離脱症状激しい
codeine
pethidine
fentanyl
methadone
l-alpha-acetylmethadol acetate LAMM
buprenorphine Temgesic

4. hallucinogens and related agents

cannabis(marijuana(tetrahydrocannabinol THC,hashish)　精神依存有り。身体依存無し　精神依存軽度。耐性は長期使用で軽度出現　大麻草
lysergic acid diethylamide LSD
phencyclidine PCP angel dust
psilocybin
mescaline

精神依存、身体依存

	精神依存	身体依存
コカイン、アンフェタミン類(アンフェタミン、メチルフェタミン)、大麻	○
麻薬(モルヒネ、ヘロイン、コデイン)、バルビツール酸系(フェノバルビタール、チオペンタール)、アルコール	○	○

「譫妄」

　　[★]

譫妄

「せん妄」を使うのが普通らしいよ
英: delirium, confusional state
同: せん妄。急性錯乱状態 acute confusional state、急性脳症候群 acute brain syndrome
関: 意識障害。アメンチア　←　せん妄の軽度なものとして使われていたが、今日で使われるのは稀らしい。

定義

意識混濁+精神運動興奮

種々の意識混濁があって、時間、空間の見当識障害が見られ、情動不穏、精神運動興奮が見られる状態

概念

軽度ないし中等度の意識混濁が基底にあり、認知の障害、精神運動活動の変化を主徴とする急性の器質性精神症候群。
急性発症し日内変動を示し、数日ないし1週間くらいで消失する。

症状

患者は強い不安、恐怖状態にあり、体動が激しく、錯覚、幻覚も出現する。
見当識も障害されており、発症中の記憶はないか不完全である。

疾患との関連

手術後、感染症等の身体的疾患、薬物中毒、多発性脳梗塞、痴呆など脳機能が低下しているときに発生しやすい

病因

table 26-2 譫妄の主要な病因 (HIM.160)

毒物

処方薬：抗コリン薬、麻薬、ベンゾジアゼピン系薬
薬物乱用：アルコール中毒、アルコール離脱、オピオイド系薬、エクスタシ、LSD、γ-ヒドロキシ酪酸(GHB, γ-hydroxybutyrate)、フェンシクリジン(PCP, phencyclidine)

代謝

電解質異常：低血糖、高血糖、低ナトリウム血症、高ナトリウム血症、高カルシウム血症、低カルシウム血症、低マグネシウム血症、低体温、高体温
肺不全：低酸素血症、高炭酸ガス血症
肝不全、肝性脳症
腎不全、尿毒症
心不全
ビタミン欠乏症：ビタミンB12、チアミン、葉酸、ナイアシン
脱水、低栄養
貧血

感染症

全身感染症：尿路感染症、肺炎、皮膚・軟部組織感染症、敗血症
中枢神経感染症：髄膜炎、脳炎、脳の右葉

内分泌

心血管疾患

全身性低灌流状態(global hypoperfusion states)
高血圧性脳症
巣状虚血性梗塞や出血：頭頂葉、視床(ただ主要な病変部位ではない)

自己免疫性疾患

中枢神経性血管炎
脳ループス

てんかん関連疾患

非痙攣性てんかん重積状態
intermittent seizures with prolonged post-ictal states

腫瘍性疾患

脳へのびまん性転移
癌性髄膜炎
大脳神経膠腫症

入院
終末期の譫妄

「セロトニン症候群」

　　[★]

英: serotonin syndrome
関: セロトニン、セロトニン受容体

概念

抗うつ薬(特に SSRI と呼ばれる選択的セロトニン再取り込み阻害薬。≒セロトニン受容体作動薬)などのセロトニン系の薬物を服用中に出現する副作用
精神症状（不安、混乱する、いらいらする、興奮する、動き回るなど）
錐体外路症状（手足が勝手に動く、震える、体が固くなるなど）
自律神経症状（汗をかく、発熱、下痢、脈が速くなるなど）
服薬開始数時間以内に症状が表れることが多い
服薬を中止すれば24時間以内に症状は消失

「不安」、「混乱する」、「いらいらする」に加えて以下の症状がみられる場合に医療機関受診を推奨している(参考1)

｢興奮する｣、「動き回る」、「手足が勝手に動く」、｢眼が勝手に動く｣、｢震える｣、「体が固くなる｣、「汗をかく｣、｢発熱｣、｢下痢｣、「脈が速くなる」

原因となりうる薬剤

トリプトファン、アンフェタミン、コカイン、MDMA、LSD、レボドパ、カルビドパ、トラマドール、ペンタゾシン、メペリジン、SSRI、SNRI、TCA、MAO阻害薬、リネゾリド、5-HT3阻害薬(オンダンセトロン、グラニセトロン)、メトクロプラミド(プリンペラン)、バルプロ酸、カルバマゼピン、シブトラミン(やせ薬)、シクロベンザプリン(中枢性筋弛緩)デキストロメルファン、(メジコン)、ブスピロン(5-HT1A阻害薬、抗不安薬)、トリプタン製剤、エルゴタミン、フェンタニル、リチウム

診断基準

QJM. 2003 Sep;96(9):635-42

Hunter criteria

感度84%, 特異度97%

セロトニン作動薬の内服歴と下記の1つ以上

1. 自発的なミオクローヌス
2. 誘発クローヌスと興奮ないし発汗
3. 眼球クローヌスと興奮ないし発汗
4. 振戦と腱反射亢進
5. 筋強剛
6. BTが38℃以上で眼球クローヌスないし誘発クローヌス

参考

1. 重篤副作用疾患別対応マニュアル

http://www.pmda.go.jp/files/000144659.pdf

「健忘」

　　[★]

英: amnesia
関: 記憶消失、記憶喪失、健忘症、健忘性

概念

記憶障害の1つである。
出来事を過去にさかのぼって思い出せない場合や、新たな出来事を覚えることができなくなる場合を指して言う。
最も良くある原因としては、頭部外傷、てんかん、片頭痛

分類

鑑別疾患

V vascular：脳動脈硬化症、脳出血、脳血栓症、脳塞栓症、片頭痛。一過性脳虚血発作。
I inflammatory：髄膜炎、脳膿瘍、マラリア、脳寄生虫、神経梅毒。発熱性疾患(発熱と健忘を来しうる)
N neoplasm：原発性脳腫瘍や転移性脳腫瘍は一時的な記憶喪失を起こしうる。
D deficiency：ウェルニッケ脳症、ペラグラ、悪性貧血。
I intoxication：LSD、アルコール、臭素化合物、オピオイド。尿毒症、低酸素血症、および肝不全も健忘を来しうる。
C convulsive：側頭葉てんかん
A autoimmune：ループス脳炎など
T trauma：脳挫傷、硬膜外血腫、硬膜下血腫
E endocrine：低血糖、糖尿病性アシドーシス、副甲状腺機能低下症、低カルシウム血症はてんかんや一過性健忘を来しうる。emotional：ヒステリー、うつ病、統合失調症。仮病。

「濫用薬物」

　　[★]

see 薬物濫用

毒物及び劇薬取締法	毒物	シアン化合物、ヒ素、黄リン、水銀、ニコチン
	劇物	硫酸、硝酸、塩酸、メタノール
	特定毒物	パラチオン、四アルキル鉛、メタノール
	毒薬	アトロピン、ジギタリス配糖体、スコポラミン、ストリキニーネ
	劇薬	カフェイン、プロカイン
麻薬及び向精神薬取締法	麻薬	アヘンアルカロイド、コカイン、合成麻薬、LSD
	第1腫向精神薬	セロバルビタール、メチルフェニデート
	第2腫向精神薬	アキサゾラム、ペンタゾシン、ペントバルビタール
	第3腫向精神薬	アロバルビタール、オキサゾラム、クロルジアゼポキシド、ジアゼパム、トリアゾラム、フェノバルビタール、トラゼパム
覚醒剤取締法	覚醒剤	アンフェタミン、メタンフェタミン
大麻取締法	大麻	大麻草及び製品
あへん法	けし属	けし、けしがら、アヘン

「LS」

　　[★]

リンパ肉腫 lymphosarcoma
最小二乗, least-square, least-squares, 最小二乗法
光覚弁 light sense sensus luminis
変形性腰椎症 lumbar spondylosis

「L」

　　[★]

[1] Halpern, John H.; Suzuki, Joji; Huertas,, Pedro E.; Passie, Torsten (7 June 2014). Price, Lawrence H.; Stolerman, Ian P., eds. Encyclopedia of Psychopharmacology A Springer Live Reference. Heidelberg, Germany: Springer-Verlag Berlin Heidelberg. pp. 1–5. ISBN 978-3-642-27772-6. Retrieved 24 April 2015. Hallucinogen abuse and dependence are known complications resulting from the illicit use of drugs in this category, such as LSD and psilocybin. Users do not experience withdrawal symptoms, but the general criteria for substance abuse and dependence otherwise apply. Dependence is estimated in approximately 2 % of recent-onset users in the United States.

[NHM-MDMA-2] Malenka RC, Nestler EJ, Hyman SE (2009). "Chapter 15: Reinforcement and Addictive Disorders". In Sydor A, Brown RY. Molecular Neuropharmacology: A Foundation for Clinical Neuroscience (2nd ed.). New York: McGraw-Hill Medical. p. 375. ISBN 9780071481274. Several other classes of drugs are categorized as drugs of abuse but rarely produce compulsive use. These include psychedelic agents, such as lysergic acid diethylamide (LSD), which are used for their ability to produce perceptual distortions at low and moderate doses. The use of these drugs is associated with the rapid development of tolerance and the absence of positive reinforcement (Chapter 6). Partial agonist effects at 5HT2A receptors are implicated in the psychedelic actions of LSD and related hallucinogens. 3,4-Methylenedioxymethamphetamine (MDMA), commonly called ecstasy, is an amphetamine derivative. It produces a combination of psychostimulant-like and weak LSD-like effects at low doses. Unlike LSD, MDMA is reinforcing—most likely because of its interactions with dopamine systems—and accordingly is subject to compulsive abuse. The weak psychedelic effects of MDMA appear to result from its amphetamine-like actions on the serotonin reuptake transporter, by means of which it causes transporter-dependent serotonin efflux. MDMA has been proven to produce lesions of serotonin neurons in animals and humans.

[Aghajanian-3] Aghajanian GK, Bing OH (1964). "Persistence of lysergic acid diethylamide in the plasma of human subjects" (PDF). Clinical Pharmacology and Therapeutics 5: 611–614. PMID 14209776. Retrieved September 17, 2009.

[Papac-4] Papac DI, Foltz RL (May–June 1990). "Measurement of lysergic acid diethylamide (LSD) in human plasma by gas chromatography/negative ion chemical ionization mass spectrometry" (PDF). Journal of Analytical Toxicology 14 (3): 189–190. doi:10.1093/jat/14.3.189. PMID 2374410. Retrieved September 17, 2009.

[5] "Definition of "amide"". Collins English Dictionary. Retrieved 2015-01-31.

[6] "American Heritage Dictionary Entry: amide". Ahdictionary.com. Retrieved 2015-01-31.

[7] "amide - definition of amide in English from the Oxford dictionary". Oxforddictionaries.com. Retrieved 2015-01-31.

[pmid17105338-8] Lüscher C, Ungless MA (November 2006). "The Mechanistic Classification of Addictive Drugs". PLoS Med. 3 (11): e437. doi:10.1371/journal.pmed.0030437. PMC 1635740. PMID 17105338.

[Passie-2008-9] Passie T, Halpern JH, Stichtenoth DO, Emrich HM, Hintzen A (2008). "The Pharmacology of Lysergic Acid Diethylamide: a Review" (PDF). CNS Neuroscience & Therapeutics 14 (4): 295–314. doi:10.1111/j.1755-5949.2008.00059.x. PMID 19040555.

[problem-child-10] Hofmann, Albert. LSD—My Problem Child (McGraw-Hill, 1980). ISBN 0-07-029325-2.

[tihkal-11] ^ ^a ^b ^c ^d ^e ^f ^g Alexander and Ann Shulgin. "LSD", in TiHKAL (Berkeley: Transform Press, 1997). ISBN 0-9630096-9-9.

[12] Albert Hofmann. "LSD – My Problem Child (English translation)".

[greiner-13] Greiner T, Burch NR, Edelberg R (1958). "Psychopathology and psychophysiology of minimal LSD-25 dosage; a preliminary dosage-response spectrum". AMA Arch Neurol Psychiatry 79 (2): 208–10. doi:10.1001/archneurpsyc.1958.02340020088016. PMID 13497365.

[14] "Hallucinogenic effects of LSD discovered". The History Channel.

[15] Arthur Stoll and Albert Hofmann LSD Patent April 30, 1943 in Switzerland and March 23, 1948 in the United States.

[16] "LSD: cultural revolution and medical advances". Royal Society of Chemistry. Retrieved September 27, 2007.

[17] Harris, Sam (2014), "The spiritual uses of pharmacology", Waking Up: A Guide to Spirituality Without Religion, Simon and Schuster, pp. 186–200, ISBN 9781451636017, I found psilocybin and LSD to be indispensable tools, and some of the most important hours of my life were spent under their influence ... psychedelics ... often reveal, in the span of a few hours, depths of awe and understanding that can otherwise elude us for a lifetime.

[linton-langs-18] Linton Harriet B., Langs Robert J. (1962). "Subjective Reactions to Lysergic Acid Diethylamide (LSD-25)" (PDF). Arch. Gen. Psychiat 6 (5): 352–68. doi:10.1001/archpsyc.1962.01710230020003.

[19] Albert Hofmann. "5. From Remedy to Inebriant". LSD: My Problem Child. ...taste of metal on the palate.

[20] Katz MM, Waskow IE, Olsson J (1968). "Characterizing the psychological state produced by LSD". J Abnorm Psychol 73 (1): 1–14. doi:10.1037/h0020114. PMID 5639999.

[21] See, e.g., Gerald Oster's article "Moiré patterns and visual hallucinations". Psychedelic Rev. No. 7 (1966): 33–40.

[22] Liester, MB (2014). "A review of lysergic acid diethylamide (LSD) in the treatment of addictions: historical perspectives and future prospects." (PDF). Current drug abuse reviews 7 (3): 146–56. doi:10.2174/1874473708666150107120522. PMID 25563445. Retrieved 27 April 2015.

[23] "DrugFacts: Hallucinogens - LSD, Peyote, Psilocybin, and PCP". National Institute on Drug Abuse. December 2014. Retrieved 17 February 2015.

[24] Alcohol and Drugs in North America: A Historical Encyclopedia, by David M. Fahey and Jon S. Miller, Editors, ISBN 978-1-59884-478-8, page 375

[25] San Francisco Chronicle September 20, 1966 Page One

[Grof1979-26] Grof, Stanislav; Joan Halifax Grof (1979). Realms of the Human Unconscious (Observations from LSD Research). London: Souvenir Press (E & A) Ltd. pp. 13–14. ISBN 0-285-64882-9.

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Systematic (IUPAC) name

(6aR,9R)-N,N-diethyl-7-methyl-4,6,6a,7,8,9-hexahydroindolo-[4,3-fg]quinoline-9-carboxamide
Clinical data
Pregnancy category	US: C (Risk not ruled out)
Legal status	AU: S9 (Prohibited) CA: Schedule III DE: Anlage I NZ: Class A UK: Class A US: Schedule I UN: Psychotropic Schedule I
Dependence liability	Low^[1]
Addiction liability	None^[2]
Routes of administration	Oral, sublingual, intravenous, ocular, intramuscular
Pharmacokinetic data
Metabolism	Hepatic
Biological half-life	3–5 hours^[3]^[4]
Excretion	Renal
Identifiers
CAS Number	50-37-3^Y
ATC code	None
PubChem	CID: 5761
IUPHAR/BPS	17
DrugBank	DB04829^Y
ChemSpider	5558^Y
UNII	8NA5SWF92O^Y
ChEBI	CHEBI:6605^Y
ChEMBL	CHEMBL263881^Y
Synonyms	Acid, LSD, lysergide
Chemical data
Formula	C₂₀H₂₅N₃O
Molecular mass	323.44 g·mol⁻¹
SMILES CCN(CC)C(=O)[C@H]1CN([C@@H]2Cc3c[nH]c4c3c(ccc4)C2=C1)C
InChI InChI=1S/C20H25N3O/c1-4-23(5-2)20(24)14-9-16-15-7-6-8-17-19(15)13(11-21-17)10-18(16)22(3)12-14/h6-9,11,14,18,21H,4-5,10,12H2,1-3H3/t14-,18-/m1/s1^Y Key:VAYOSLLFUXYJDT-RDTXWAMCSA-N^Y
Physical data
Melting point	80 to 85 °C (176 to 185 °F)
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匿名

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案内

LSD