Lysergic acid diethylamide

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"LSD" redirects here. For other uses, see LSD (disambiguation).

Lysergic acid diethylamide (LSD)

INN: Lysergide

2D structural formula and 3D models of LSD

Clinical data

Pronunciation /daɪ eθəl ˈæmaɪd/, /æmɪd/, or /eɪmaɪd/)[3][4][5]

Synonyms Lyserg-säure-diäthylamid, LSD, LSD-25, Acid, Delysid, others

AHFS/Drugs.com Reference

Pregnancy  US: C (Risk not ruled out)

category

Dependence Low[1]
liability

Addiction Low-rare[2]
liability

Routes of By mouth, under the tongue, intravenous, intramuscular,

administration
or subcutaneous injection; rectal, insufflation, eye drops

Drug class Psychedelic (serotonergic psychedelic)

ATC code  None

Legal status

Legal status  AU: S9 (Prohibited)

 CA: Schedule III

 DE: Anlage I (Authorized scientific use only)

 NZ: Class A
  UK: Class A

 US: Schedule I

 UN: Psychotropic Schedule I

Pharmacokinetic data

Bioavailability 71%[6]

Protein binding Unknown[7]

Metabolism Hepatic (CYP450)[6]

Metabolites 2-Oxo-3-hydroxy-LSD[6]

Onset of action 30–40 minutes[8]

Biological half-life 3.6 hours[9][6]

Duration of action 8–12 hours[10]

Excretion Renal[9][6]

Identifiers

IUPAC name[show]

CAS Number 50-37-3

PubChem CID 5761

IUPHAR/BPS 17

DrugBank  DB04829

ChemSpider  5558

UNII  8NA5SWF92O

ChEBI  CHEBI:6605

ChEMBL  CHEMBL263881

PDB ligand  7LD (PDBe, RCSB PDB)

ECHA InfoCard 100.000.031

Chemical and physical data

Formula C20H25N3O

Molar mass 323.44 g·mol−1

 Interactive image
3D model (JSmol)

Melting point 80 to 85 °C (176 to 185 °F)

SMILES[show]
 InChI[show]

(verify)

Lysergic acid diethylamide (LSD), also known as acid, is a psychedelic drug known for its
psychological effects, which may include altered awareness of one's surroundings, perceptions,
and feelings as well as sensations and images that seem real though they are not.[11] It is used
mainly as a recreational drug and for spiritual reasons. LSD is typically either swallowed or held
under the tongue.[11] It is often sold on blotter paper, a sugar cube, or gelatin. It can also be
injected.
LSD is not usually addictive.[11][12] However, adverse psychiatric reactions such
as anxiety, paranoia, and delusions are possible.[7] LSD is in the ergoline family. LSD is sensitive
to oxygen, ultraviolet light, and chlorine,[13] though it may last for years if it is stored away from
light and moisture at low temperature. In pure form it is odorless, crystalline, and clear or white in
color.[11] As little as 20–30 micrograms can produce an effect.[14]
LSD was first made by Albert Hofmann in Switzerland in 1938 from ergotamine, a chemical from
the fungus ergot. The laboratory name for the compound was the acronym for the German
"Lyserg-säure-diäthylamid", followed by a sequential number: LSD-25.[13][15] Hofmann discovered
its psychedelic properties in 1943.[16] LSD was introduced as a commercial medication under the
trade-name Delysid for various psychiatric uses in 1947.[17] In the 1950s, officials at the United
States Central Intelligence Agency (CIA) thought the drug might be useful for mind
control and chemical warfare and tested the drug on young servicemen and students, and others
without their knowledge. The subsequent recreational use by youth culture in the Western
world as part of 1960s counterculture resulted in its prohibition.[18]

Contents
[hide]

 1Uses
o 1.1Medical
o 1.2Recreational
o 1.3Spiritual
 2Effects
o 2.1Physical
o 2.2Psychological
o 2.3Sensory
 3Adverse effects
o 3.1Mental disorders
o 3.2Suggestibility
o 3.3Flashbacks
o 3.4Pregnancy
o 3.5Tolerance
 4Overdose
 5Pharmacology
o 5.1Pharmacodynamics
o 5.2Pharmacokinetics
 6Chemistry
o 6.1Synthesis
o 6.2Dosage
o 6.3Reactivity and degradation
o 6.4Detection in body fluids
 7History
 8Society and culture
o 8.1Counterculture, music and art
o 8.2Legal status
o 8.3Economics
 9Research
o 9.1Psychedelic therapy
o 9.2Other uses
 10Notable individuals
 11See also
 12References
 13Further reading
 14External links

Uses
Medical
See also: Lysergic acid diethylamide § Research
LSD currently has no approved uses in medicine.[19][20] A meta analysis concluded that a single
dose was effective at reducing alcohol consumption in alcoholism.[21] LSD has also been studied
in depression, anxiety, and drug dependence, with positive preliminary results.[22]
Recreational

Pink elephant blotters containing LSD

LSD is commonly used as a recreational drug.[23]

Spiritual
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
sometimes report 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 texts of ancient civilizations.[26]

Effects
Some symptoms reported for LSD.[27][28]

Physical
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, hyperreflexia, and tremors.[medical
citation needed]

Psychological
The most common immediate psychological effects of LSD are visual
hallucinations and illusions (colloquially known as "trips"), which can vary greatly depending on
how much is used and how the brain responds. Trips usually start within 20–30 minutes of taking
LSD by mouth (less if snorted or taken intravenously), peak three to four hours after ingestion,
and last up to 12 hours. Negative experiences, referred to as "bad trips", produce intense
negative emotions, such as irrational fears and anxiety, panic attacks, paranoia, rapid mood
swings, intrusive thoughts of hopelessness, wanting to harm others, and suicidal ideation. It is
impossible to predict when a bad trip will occur.[29][30] Good trips are stimulating and pleasurable,
and typically involve feeling as if one is floating, disconnected from reality, feelings of joy or
euphoria (sometimes called a "rush"), decreased inhibitions, and the belief that one has extreme
mental clarity or superpowers.[29]
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.[31] Some
users, including Albert Hofmann, report a strong metallic taste for the duration of the effects.[32]
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.[31][33] 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.[34] 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]

Adverse effects

Addiction experts in psychiatry, chemistry, pharmacology, forensic science, epidemiology, and the police and legal services engaged

in delphic analysis regarding 20 popular recreational drugs. LSD was ranked 14th in dependence, 15th in physical harm, and 13th in

social harm.[35]

Of the 20 drugs ranked according to individual and societal harm by David Nutt, LSD was third to
last, approximately 1/10th as harmful as alcohol. The most significant adverse effect was
impairment of mental functioning while intoxicated.[36]
Mental disorders
LSD may trigger panic attacks or feelings of extreme anxiety, known familiarly as a "bad trip."
Review studies suggest that LSD likely plays a role in precipitating the onset of acute psychosis
in previously healthy individuals with an increased likelihood in individuals who have a family
history of schizophrenia.[7][37] There is evidence that people with severe mental illnesses
like schizophrenia have a higher likelihood of experiencing adverse effects from taking LSD.[37]
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,[38] research from the 1960s
suggests that both mentally ill and healthy people are more suggestible while under its
influence.[39][40][non-primary source needed]
Flashbacks
See also: Flashback (psychology)
Some individuals may experience "flashbacks" and a syndrome of long-term and occasionally
distressing perceptual changes.[41][42]
"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".[43] Several studies have tried to determine the likelihood that a user
of LSD, not suffering from known psychiatric conditions, will experience flashbacks. The larger
studies include Blumenfeld's in 1971[43][44][45][46][47] and Naditch and Fenwick's in 1977,[48][49][50][51][52] which
arrived at figures of 20%[44] and 28%,[48] respectively.[41][53][54]
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.[55] 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.[56][57]
Pregnancy
The mutagenic potential of LSD is unclear. Overall, the evidence seems to point to limited or no
effect at commonly used doses.[58]
Tolerance
Tolerance to LSD builds up over consistent use[59] and cross-tolerance has been demonstrated
between LSD, mescaline[60] and psilocybin.[61] This tolerance is probably caused
by downregulation of 5-HT2A receptors in the brain and diminishes a few days after cessation of
use.
LSD is not addictive.[2][12][62] Experimental evidence has demonstrated that LSD use does not
yield positive reinforcement in either human or animal subjects.[2][63][64]

Overdose
As of 2008 there were no documented fatalities attributed directly to an LSD overdose.[65] Despite
this several behavioral fatalities and suicides have occurred due to LSD.[66][67]Eight individuals who
accidentally consumed very high amounts by mistaking LSD for cocaine developed comatose
states, hyperthermia, vomiting, gastric bleeding, and respiratory problems however all survived
with supportive care.[65]
Reassurance in a calm, safe environment is beneficial. Agitation can be safely addressed
with benzodiazepines such as lorazepam or diazepam. Neuroleptics such as haloperidolare
recommended against because 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 an overdose of LSD. Sedation or physical restraint is rarely required, and
excessive restraint may cause complications such as hyperthermia (over-heating)
or rhabdomyolysis.[68]
Research suggests that massive doses are not lethal, but do typically require supportive care,
which may include endotracheal intubation or respiratory support.[68] It is recommended that high
blood pressure, tachycardia (rapid heart-beat), and hyperthermia, if present, are treated
symptomatically, and that low blood pressure is treated initially with fluids and then
with pressors if necessary. Intravenous administration of anticoagulants, vasodilators,
and sympatholytics may be useful with massive doses.[68]

Pharmacology
Pharmacodynamics
Binding affinities of LSD for various receptors. The lower the dissociation constant (Ki), 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 Ki Database

Most serotonergic psychedelics are not significantly dopaminergic, and LSD is therefore atypical
in this regard. The agonism of the D2receptor by LSD may contribute to its psychoactive effects in
humans.[69][70]
LSD binds to most serotonin receptor subtypes except for the 5-HT3 and 5-HT4 receptors.
However, most of these receptors are affected at too low affinity to be sufficiently activated by the
brain concentration of approximately 10–20 nM.[62] In humans, recreational doses of LSD can
affect 5-HT1A (Ki=1.1nM), 5-HT2A (Ki=2.9nM), 5-HT2B (Ki=4.9nM), 5-HT2C (Ki=23nM), 5-HT5A (Ki=9nM
[in cloned rat tissues]), and 5-HT6receptors (Ki=2.3nM).[71][72] 5-HT5B receptors, which are not
present in humans, also have a high affinity for LSD.[73] The psychedelic effects of LSD are
attributed to cross-activation of 5-HT2A receptor heteromers.[74] Many but not all 5-
HT2A agonists are psychedelics and 5-HT2Aantagonists block the psychedelic activity of LSD. LSD
exhibits functional selectivity at the 5-HT2A and 5HT2C receptors in that it activates the signal
transduction enzyme phospholipase A2 instead of activating the enzyme phospholipase C as the
endogenous ligand serotonin does.[75] Exactly how LSD produces its effects is unknown, but it is
thought that it works by increasing glutamate release in the cerebral cortex[62] and
therefore excitation in this area, specifically in layers IV and V.[76] LSD, like many other drugs of
recreational use, has been shown to activate DARPP-32-related pathways.[77] The drug enhances
dopamine D2 receptor protomer recognition and signaling of D2–5-HT2A receptor
complexes,[78] which may contribute to its psychotic effects.[78]
The crystal structure of LSD bound in its active state to a serotonin receptor, specifically the 5-
HT2B receptor, has recently (2017) been elucidated for the first time.[79][80][81] The LSD-bound 5-
HT2B receptor is regarded as an excellent model system for the 5-HT2A receptor and the structure
of the LSD-bound 5-HT2B receptor was used in the study as a template to determine the structural
features necessary for the activity of LSD at the 5-HT2A receptor.[79][80][81] The diethylamide moiety of
LSD was found to be a key component for its activity, which is in accordance with the fact that
the related lysergamide lysergic acid amide (LSA) is far less hallucinogenic in comparison.[81] LSD
was found to stay bound to both the 5-HT2A and 5-HT2B receptors for an exceptionally long amount
of time, which may be responsible for its long duration of action in spite of its relatively short
terminal half-life.[79][80][81] The extracellular loop 2 leucine 209 residue of the 5-HT2B receptor forms
a 'lid' over LSD that appears to trap it in the receptor, and this was implicated in
the potency and functional selectivity of LSD and its very slow dissociation ratefrom the 5-
HT2 receptors.[79][80][81]
Pharmacokinetics
The effects of LSD normally last between 6 and 12 hours depending on dosage, tolerance, body
weight, and age.[13] The Sandoz prospectus for "Delysid" warned: "intermittent disturbances of
affect may occasionally persist for several days."[15] 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.[citation needed][contradictory] Aghajanian and Bing (1964) found LSD had an elimination half-life of
only 175 minutes (about 3 hours).[71]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.[82]
The pharmacokinetics of LSD were not properly determined until 2015, which is not surprising for
a drug with the kind of low-μg potency that LSD possesses.[9][6] In a sample of 16 healthy subjects,
a single mid-range 200 μg oral dose of LSD was found to produce mean maximal
concentrations of 4.5 ng/mL at a median of 1.5 hours (range 0.5–4 hours) post-
administration.[9][6] After attainment of peak levels, concentrations of LSD decreased following first-
order kinetics with a terminal half-life of 3.6 hours for up to 12 hours and then with
slower elimination with a terminal half-life of 8.9 hours thereafter.[9][6] The effects of the dose of
LSD given lasted for up to 12 hours and were closely correlated with the concentrations of LSD
present in circulation over time, with no acute tolerance observed.[9][6] Only 1% of the drug was
eliminated in urine unchanged whereas 13% was eliminated as the major metabolite 2-oxo-3-
hydroxy-LSD (O-H-LSD) within 24 hours.[9][6] O-H-LSD is formed by cytochrome P450 enzymes,
although the specific enzymes involved are unknown, and it does not appear to be known
whether O-H-LSD is pharmacologically active or not.[9][6] The oral bioavailability of LSD was
crudely estimated as approximately 71% using previous data on intravenous administration of
LSD.[9][6] The sample was equally divided between male and female subjects and there were no
significant sex differences observed in the pharmacokinetics of LSD.[9][6]

Chemistry

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.[13] LSD is strongly fluorescent and will glow bluish-white under UV light.
Synthesis
LSD is an ergoline derivative. It is commonly synthesized by reacting diethylamine with an
activated form of lysergic acid. Activating reagents include phosphoryl chloride[83] and peptide
coupling reagents.[84] 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.[85] Lysergic acid can also be produced synthetically, eliminating the
need for ergotamines.[86][87]
Dosage
White on White blotters (WoW) for sublingual administration

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.[14][88] 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.[15]
In the mid-1960s, the most important black market LSD manufacturer (Owsley Stanley)
distributed acid at a standard concentration of 270 µg,[89] 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,[90] and even more in the 2000s (decade).[89][91]
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."[13]
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.[13] 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.[13]
A controlled study was undertaken to determine the stability of LSD in pooled urine
samples.[92] 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.[93]
The apparent plasma half life of LSD is considered to be around 5.1 hours with peak plasma
concentrations occurring 3 hours after administration.[94]

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[95]

Main article: History of lysergic acid diethylamide

LSD was first synthesized on November 16, 1938[96] 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 psychedelicproperties were discovered 5 years
later when Hofmann himself accidentally ingested an unknown quantity of the chemical.[97] The
first intentional ingestion of LSD occurred on April 19, 1943,[98] 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.[99] Sandoz Laboratories
introduced LSD as a psychiatric drug in 1947.[100]

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.[90] 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.[101] In the early 1960s the use of LSD and other hallucinogens was
advocated by new proponents of consciousness expansion such as Leary, Huxley, Alan
Watts and Arthur Koestler,[102][103] and according to L. R. Veysey they profoundly influenced the
thinking of the new generation of youth.[104]
On October 24, 1968, possession of LSD was made illegal in the United States.[105] 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.[106]

Society and culture

Counterculture, music and art
Main article: LSD art
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Psychedelic art attempts to capture the visions experienced on a psychedelic trip

By the mid-1960s, the youth countercultures in California, particularly in San Francisco, had
adopted the use of hallucinogenic drugs, with the first major underground LSD factory
established by Owsley Stanley.[107] From 1964, the Merry Pranksters, a loose group that
developed around novelist Ken Kesey, sponsored the Acid Tests, a series of events primarily
staged in or near San Francisco, involving the taking of LSD (supplied by Stanley), accompanied
by light shows, film projection and discordant, improvised music known as the psychedelic
symphony.[108][109] The Pranksters helped popularize LSD use, through their road trips across
America in a psychedelically-decorated converted school bus, which involved distributing the
drug and meeting with major figures of the beat movement, and through publications about their
activities such as Tom Wolfe's The Electric Kool-Aid Acid Test (1968).[110] In both music and art,
the influence of LSD was soon being more widely seen and heard thanks to the bands that
participated in the Acid Tests and related events, including the Grateful Dead, Jefferson
Airplane and Big Brother and the Holding Company, and through the inventive poster and album
art of San Francisco-based artists like Rick Griffin, Victor Moscoso, Bonnie MacLean, Stanley
Mouse & Alton Kelley, and Wes Wilson, meant to evoke the visual experience of an LSD trip.
In San Francisco's Haight-Ashbury neighborhood, brothers Ron and Jay Thelin opened the
Psychedelic Shop in January 1966. The Thelins' store is regarded as the first ever head shop.
The Thelins opened the store to promote safe use of LSD, which was then still legal in California.
The Psychedelic Shop helped to further popularize LSD in the Haight and to make the
neighborhood the unofficial capital of the hippie counterculture in the United States. Ron Thelin
was also involved in organizing the Love Pageant rally, a protest held in Golden Gate park to
protest California's newly adopted ban on LSD in October 1966. At the rally, hundreds of
attendees took acid in unison. Although the Psychedelic Shop closed after barely a year-and-a-
half in business, its role in popularizing LSD was considerable.[111]

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Lysergic Acid Diethylamide, by Lambert P. Lambert and the Gorgettes, from the album Abbra Cadaver, 1967.

A similar and connected nexus of LSD use in the creative arts developed around the same time
in London. A key figure in this phenomenon in the UK was British academic Michael
Hollingshead, who first tried LSD in America in 1961 while he was the Executive Secretary for
the Institute of British-American Cultural Exchange. After being given a large quantity of pure
Sandoz LSD (which was still legal at the time) and experiencing his first "trip", Hollingshead
contacted Aldous Huxley, who suggested that he get in touch with Harvard academic Timothy
Leary, and over the next few years, in concert with Leary and Richard Alpert, Hollingshead
played a major role in their famous LSD research at 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. Among the many famous people in
the UK that Hollingshead is reputed to have introduced to LSD are artist
and Hipgnosis founder Storm Thorgerson, and musicians Donovan, Keith Richards, Paul
McCartney, John Lennon, and George Harrison. Although establishment concern about the new
drug led to it being declared an illegal drug by the Home Secretary in 1966, LSD was soon being
used widely in the upper echelons of the British 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 being both heard and seen by the
public with singles like The Small Faces' "Itchycoo Park" and LPs like the Beatles' Sgt Pepper's
Lonely Hearts Club Band and Cream's Disraeli Gears, which featured music that showed the
obvious influence of the musicians' recent psychedelic excursions, and which were packaged in
elaborately-designed album covers that featured vividly-coloured psychedelic artwork by artists
like Peter Blake, Martin Sharp, Hapshash and the Coloured Coat (Nigel Waymouth and Michael
English) and art/music collective "The Fool".
In the 1960s, musicians from psychedelic music and psychedelic rock bands began to refer (at
first indirectly, and later explicitly) to the drug and attempted to recreate or reflect the experience
of taking LSD in their music. A number of features are often included in psychedelic music.
Exotic instrumentation, with a particular fondness for the sitar and tabla are common.[112] Electric
guitars are used to create feedback, and are played through wah wah and fuzzbox effect
pedals.[113] Elaborate studio effects are often used, such as backwards tapes, panning, phasing,
long delay loops, and extreme reverb.[114] In the 1960s there was a use of primitive electronic
instruments such as early synthesizers and the theremin.[115][116] Later forms of electronic
psychedelia also employed repetitive computer-generated beats.[117] Songs allegedly referring to
LSD include John Prine's "Illegal Smile" and The Beatles' song Lucy in the Sky with Diamonds,
although the authors of the latter song repeatedly denied this claim.[118][119][120] Psychedelic
experiences were also reflected in psychedelic art, literature and film.[121]
LSD had a strong influence on the Grateful Dead and the culture of Deadheads, as well as the
impact for artist Keith Haring, early techno music, and the jam band Phish.[122]
Legal status
The United Nations Convention on Psychotropic Substances (adopted in 1971) requires the
signing parties to prohibit LSD. Hence, it is illegal in all countries that were parties to the
convention, including the United States, Australia, New Zealand, and most of Europe. However,
enforcement of those laws varies from country to country. Medical and scientific research with
LSD in humans is permitted under the 1971 UN Convention.[123]
Australia
LSD is a Schedule 9 prohibited substance in Australia under the Poisons Standard (February
2017).[124] A Schedule 9 substance is defined as a substance 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 Commonwealth and/or State or Territory Health Authorities.[124]
In Western Australia section 9 of the Misuse of Drugs Act 1981 provides for summary trial before
a magistrate for possession of less than 0.004g; section 11 provides rebuttable presumptions of
intent to sell or supply if the quantity is 0.002g or more, or of possession for the purpose of
trafficking if 0.01g.[125]
Canada
In Canada, LSD is a controlled substance under Schedule III of the Controlled Drugs and
Substances Act.[126] 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 recognized
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".[127]
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.[128]
United States
LSD is Schedule I in the United States, according to the Controlled Substances Act of
1970.[129] This means LSD is illegal to manufacture, buy, possess, process, or distribute without a
license from the Drug Enforcement Administration (DEA). By classifying LSD as a Schedule I
substance, the DEA 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.[130]
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 US. 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.
United States.[131]
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.
Mexico
In April 2009, the Mexican Congress approved changes in the General Health Law that
decriminalized the possession of illegal drugs for immediate consumption and personal use,
allowing a person to possess a moderate amount of LSD. The only restriction is that people in
possession of drugs should not be within a 300-meter radius of schools, police departments, or
correctional facilities. Marijuana, along with cocaine, opium, heroin, and other drugs were also
decriminalized, it will not be considered as a crime as long as the dose does not exceed the limit
established in the General Health Law.[132] Many question this, as cocaine is as much synthesised
as heroin, both are produced as extracts from plants. The law establishes very low amount
thresholds and strictly defines personal dosage. For those arrested with more than the threshold
allowed by the law this can result in heavy prison sentences, as they will be assumed to be small
traffickers even if there are no other indications that the amount was meant for selling.[133]
Czech Republic
In the Czech Republic, until 31 December 1998 only drug possession "for other person" (i.e.
intent to sell) was criminal (apart from production, importation, exportation, offering or mediation,
which was and remains criminal) while possession for personal use remained legal.[134]
On 1 January 1999, an amendment of the Criminal Code, which was necessitated in order to
align the Czech drug rules with the Single Convention on Narcotic Drugs, became effective,
criminalizing possession of "amount larger than small" also for personal use (Art. 187a of the
Criminal Code) while possession of small amounts for personal use became a misdemeanor.[134]
The judicial practice came to the conclusion that the "amount larger than small" must be five to
ten times larger (depending on drug) than a usual single dose of an average consumer.[135]
Under the Regulation No. 467/2009 Coll, possession of more than 5 doses of LSD was to be
considered smaller than large for the purposes of the Criminal Code and was to be treated as a
misdemeanor subject to a fine equal to a parking ticket.[136]
Ecuador
According to the 2008 Constitution of Ecuador, in its Article 364, the Ecuadorian state does not
see drug consumption as a crime but only as a health concern.[137] Since June 2013 the State
drugs regulatory office CONSEP has published a table which establishes maximum quantities
carried by persons so as to be considered in legal possession and that person as not a seller of
drugs.[137][138][139] The "CONSEP established, at their latest general meeting, that the 0.020
milligrams of LSD shal be considered the maximum consumer amount.[140]
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 cocaine, cannabis, or other illegal drugs.[141]
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.[141][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.[142]
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".[143]
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.[142][143] More than 200 types of LSD
tablets have been encountered since 1969 and more than 350 blotter paper designs have been
observed since 1975.[143] 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.[142] 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.[144][145] Authorities have encountered the drug
in other forms—including powder or crystal, and capsule.[146]
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.[147] As a group, independent producers are of less concern to
the Drug Enforcement Administration than the larger groups because their product reaches only
local markets.[148]
Many LSD dealers and chemists describe a religious or humanitarian purpose that motivates
their illicit activity. Nicholas Schou's book Orange Sunshine: The Brotherhood of Eternal Love
and Its Quest to Spread Peace, Love, and Acid to the World describes one such group,
the Brotherhood of Eternal Love. The group was a major American LSD trafficking group in the
late 1960s and early 1970s.[149]
In the second half of the 20th century, dealers and chemists loosely associated with the Grateful
Dead like Owsley Stanley, Nicholas Sand, Karen Horning, Sarah Maltzer, "Dealer McDope,"
and Leonard Pickard played an essential role in distributing LSD.[122]
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,[150][151] a mixture of DOC and DOI,[152] 25I-NBOMe,[153] and a mixture
of DOC and DOB.[154]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.[155] 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.[156] Several deaths
have been attributed to 25I-NBOMe.[157][158][159][160]

Research
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.[161] New clinical LSD
experiments in humans started in 2009 for the first time in 35 years.[162] As it is illegal in many
areas of the world, potential medical uses are difficult to study.[19]
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."[163] More recently, experimental uses of LSD have included the
treatment of alcoholism[164] and pain and cluster headache relief.[165]
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,[166] and also for treating alcoholism.[167][168] One study concluded,
"The root of the therapeutic value of the LSD experience is its potential for producing self-
acceptance and self-surrender,"[169] 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.[170][171]
In recent years organizations like the Multidisciplinary Association for Psychedelic Studies have
renewed clinical research of LSD.[172]
Other uses
In the 1950s and 1960s, some psychiatrists (e.g. 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.[173][174][175][176]
Since 2008 there has been ongoing research into using LSD to alleviate anxiety for terminally
ill cancer patients coping with their impending deaths.[177][178]
A 2012 meta-analysis 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.[179]
LSD has been used as a treatment for cluster headaches with positive results in some small
studies.[165][180]

Notable individuals
 Some notable individuals have commented publicly on their experiences with LSD.[181][182] Some of
these comments date from the era when it was legally available in the US and Europe for non-
medical uses, and others pertain to psychiatric treatment in the 1950s and 1960s. Still others
describe experiences with illegal LSD, obtained for philosophic, artistic, therapeutic, spiritual, or
recreational purposes.

 Richard Feynman, a notable physicist at California Institute of Technology, tried LSD during
his professorship at Caltech. Feynman largely sidestepped the issue when dictating his
anecdotes; he mentions it in passing in the "O Americano, Outra Vez" section.[183][184]
 Jerry Garcia stated in a July 3, 1989 interview for Relix Magazine, in response to the
question "Have your feelings about LSD changed over the years?," "They haven’t changed
much. My feelings about LSD are mixed. It’s something that I both fear and that I love at the
same time. I never take any psychedelic, have a psychedelic experience, without having that
feeling of, “I don’t know what’s going to happen.” In that sense, it’s still fundamentally an
enigma and a mystery."[185]
 Bill Gates implied in an interview with Playboy that he tried LSD during his youth.[186]
 Aldous Huxley, author of Brave New World, became a user of psychedelics after moving
to Hollywood. He was at the forefront of the counterculture's experimentation with
psychedelic drugs, which led to his 1954 work The Doors of Perception. Dying from cancer,
he asked his wife on 22 November 1963 to inject him with 100 µg of LSD. He died later that
day.[187]
 Steve Jobs, co-founder and former CEO of Apple Inc., said, "Taking LSD was a profound
experience, one of the most important things in my life."[188]
 In a 2004 interview, Paul McCartney said that The Beatles' songs "Day Tripper" and "Lucy in
the Sky with Diamonds" are about LSD, although John Lennon explicitly declared that "Lucy"
was never about LSD but rather inspired by a picture drawn by his son Julian.[189][190] John
Lennon, George Harrison, and Ringo Starr also experimented with the drug, although
McCartney cautioned that "it's easy to overestimate the influence of drugs on the Beatles'
music."[191]
 Kary Mullis is reported to credit LSD with helping him develop DNA amplification technology,
for which he received the Nobel Prize in Chemistry in 1993.[192]

See also

 Pharmacy and pharmacology portal

 1960s portal

 History of lysergic acid diethylamide

 Albert Hofmann
 Timothy Leary
 LSD art
 Psychedelic microdosing
 Psychedelic therapy
 Owsley Stanley
 Urban legends about LSD

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Further reading
 Bebergal, Peter, "Will Harvard drop acid again? Psychedelic research returns to
Crimsonland", The Phoenix (Boston), June 2, 2008
 Passie T, Halpern JH, Stichtenoth DO, Emrich HM, Hintzen A (2008). "The pharmacology of
lysergic acid diethylamide: a review". CNS Neuroscience & Therapeutics. 14 (4): 295–
314. doi:10.1111/j.1755-5949.2008.00059.x. PMID 19040555.

External links