University of Belgrade

Faculty of Chemistry

Ana Nikolov
BH27/2013

LSD

Belgrade, 2014
Contents (Sadrzaj):

About LSD3

Chemistry and structure4

Effects and usage..5

Making LSD.7

References8

About LSD
LSD is a shorten term for Lysergic acid diethylamide and it is also colloquially known as acid.It
is asemisynthetic,psychedelic drug well known for its psychological effects which can also
include delusions,visual hallucinations,an artificial sense of euphoria and many more. LSD is
non-addictive, is not known to cause brain damage, and has extremely low toxicity relative to
dose.However,this is known as a very strong drug.

HISTORY
LSD was first synthesized by Albert Hofmann in 1938 from ergotamine while looking for a
blood stimulant, a chemical derived by Arthur Stoll from ergot, a grain fungus that typically
grows on rye.
Its hallucinogenic effects were unknown until 1943 when Hofmann accidentally consumed some
LSD. It was later found that an oral dose of as little as 25 micrograms (equal in weight to a few
grains of salt) is capable of producing vivid hallucinations.It was used in experiments by
psychiatrists through the 1940s, 50s and 60s because of its similarity to a chemical present in
the brain and its similarity in effects to certain aspects of psychosis.
LSD was popularized in the 1960s by individuals such as psychologist Timothy Leary, who
encouraged American students to use it. This created an entire counterculture of drug abuse and
spread the drug from America to the United Kingdom and the rest of Europe. Before it was a
recreational drug, LSD was used in psychiatric therapy. In the beginning, psychiatrists hoped that
LSD would prove to be a cure for some forms of mental illness. It was thought that giving a
patient LSD would remove the need for years of psychotherapy and bring about permanent
changes in behavior and personality.
For a few years after 1998 LSD had become more widely used at dance clubs and all-night raves
by older teens and young adults for pleasure.
LSD is sensitive to oxygen, ultraviolet light, and chlorine, especially in solution, though its
potency may last for years if it is stored away from light and moisture at low temperature.LSD is
typically delivered orally, 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. Tablet known as microdot is also very common.LSD is produced in crystalline form
and then mixed with excipients, or diluted as a liquid for production in ingestible forms. It is
odorless, colorless and has a slightly bitter taste.

Chemistry and structure

The molecular formula for lysergic acid diethylamide is C20H25N3O.

LSD is a chiral compound with two stereocenters at the carbon atoms C-5 and C-8.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.

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 isoLSD which has formed during the synthesis can be separated by chromatography and can be
isomerized to LSD which is strongly fluorescent and will glow bluish-white under UV light.

It is a non-toxic,non-addictive molecule which mimics serotonin in the brain.Our body easily

mistakes LSD for serotonin,which has a higher affinity for some receptors than serotonin and its
presence prevents serotonin from sending neural messages in the brain.When the LSD molecule
is bound to the receptor proteins,the message will not go further. The dipole moment is going
towards the amine group in both molecules. The virtually same dipole moments of both
molecules is the key to the ability of LSD fitting into the same receptors as serotonin.
"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."

LSD also has enamine-type reactivity because of the electron-donating effects of the indole ring.
Chlorine destroys LSD molecules on contact,the small quantity of compound typical to an LSD
solution will likely be eliminated when dissolved in tap water.The double bond between the 8position 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.
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In its pure form, LSD is a white or clear, odorless, water-soluble crystal that can be crushed into
a powder and dissolved.

Effects and usage

This drug causes many physical and mental effects.Common physical effects are :

dilated pupils
higher or lower body temperature
sweating or chills
loss of appetite
tremors
dry mouth.

On the other side,there are many mental effects which can last even for twelwe hours after
consuming.It can cause distortion of ones sence of time and identity, impaired time perception,
distorted perception of the size and shape of objects, movements, color, sounds, touch and the
users own body image,also severe, terrifying thoughts and feelings,fear of losing control,panic
attacks,flashbacks, or a recurrence of the LSD trip, often without warning long after taking LSD.
The effects of LSD are unpredictable.

Users never know if they are going to have a good "trip" or a bad one. Usually, the first effects of
the drug are felt 30 to 90 minutes after taking it. The user may experience extreme changes in
mood, feel several different emotions at once, or swing rapidly from one emotion to another. If
taken in large enough doses, the drug produces delusions and visual hallucinations. Sensations
may seem to "cross over," giving the feeling of hearing colors and seeing sounds. These changes
can be frightening and can cause panic. Users can see images, hear sounds, and feel sensations
that seem to be very real, but actually do not exist.

An acid flashback occurs when a person who has used LSD in the past experiences the effects of
acid use, such as hallucinations, without taking the drug again.The brain holds and may release
molecules of LSD over time, and this is what causes flashbacks.A flashback occurs suddenly,
often without warning, usually in people who use hallucinogens chronically or have an
underlying personality problem. Healthy people who use LSD occasionally may also have
them.They can appear months or even years after taking it and there is no way to control
them,just like there is no way to control the drug itself. Scientists still know little about what
causes them or how to treat them.

Users who take the drug repeatedly must take progressively higher doses to achieve the state of
intoxication that they had previously achieved. Using LSD for just a few days in a row can cause
a person to build up a tolerance quickly, so it's rarely used more than once a week. A person who
uses LSD twice a week is considered a heavy user. In addition, repeated trips tend to lose their
novelty, and what once seemed magical becomes everyday.

There have been no documented human deaths from an LSD overdose. It is well tolerated and
there is no evidence for long-lasting physiological effects on the brain or other parts of the
human organism. LSD may temporarily impair the ability to make sensible judgments and
understand common dangers.Users have accidentally killed themselves by walking in front of a
car, getting into a car accident while tripping, or falling from windows or buildings.

Heavy LSD users can also develop profound social problems, lose interest in eating and personal
hygiene. They become uninterested in participating in the world going on around them and feel
completely disconnected from everybody else. The real problem is that because they're taking
LSD so often, they think the LSD is creating the illusion that their life is a mess instead of
recognizing that it really is a mess.

As little as 0.25 micrograms of LSD per 2.2 pounds (about 1 kilogram) of body weight can
produce the effects. When a person takes LSD, it's quickly metabolized in the liver and
eventually excreted in the urine. A small amount is left in the body by the end of the trip and is
gone entirely a few weeks afterward.

Making LSD

Making LSD requires a strong working knowledge of organic chemistry, a complete laboratory
setup, access to a darkroom and several chemicals that are restricted.They can't be found in
ordinary household items.

Morning glory seeds, can be dangerous because they're sold with a toxic coating to discourage
consumption. Those seeds and the seeds of some related plants contain LSA, or lysergic acid
amide. The LSA can be extracted from the seeds and produce a mild high on its own. It's
considered a precursor to LSD, although the amount of LSA in different seeds varies so much
that the quality of the drug made from it would also vary.

Chemist has to carefully and precisely culture the fungus to extract the ergot alkaloids (an
alkaloid is a compound containing basic nitrogen atoms). The darkroom is a necessity because
the fungus will decompose under bright lights.

The solvents and reagents (compounds used to bring about chemical reactions) are also
incredibly dangerous. The solvent anhydrous hydrazine, for example, can explode when heated.
It's poisonous and a known carcinogen. Chloroform, can also cause cancer as well as severely
damage the kidneys and liver. Both of these can be easily absorbed through the skin or inhaled.

The ergot alkaloid is synthesized into a lysergic acid compound called iso-lysergic acid
hydrazide, through the addition of chemicals and heating processes. Then the iso-lysergic acid
hydrazide is isomerized, which means that the atoms in its molecules are rearranged through a
chemical process. It's cooled, mixed with an acid and a base, and evaporated. What remains
is iso-lysergic diethylamide, which is isomerized again to produce active LSD. The LSD is then
purified and crystallized.

References (Literatura):
http://sh.wikipedia.org/wiki/Dietilamid_liserginske_kiseline
http://en.wikipedia.org/wiki/Lysergic_acid_diethylamide
http://www.lsdaddiction.us/content/acid-flashbacks.html

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