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Chemistry: Hallucinogen

The document provides information about LSD including its chemistry, pharmacology, synthesis, effects, and legal status. It is a potent hallucinogen that was popular in the 1960s-1980s but is now less common. Typical doses are 20-80 micrograms and effects last 8-12 hours, including visual and sensory distortions.
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0% found this document useful (0 votes)
165 views5 pages

Chemistry: Hallucinogen

The document provides information about LSD including its chemistry, pharmacology, synthesis, effects, and legal status. It is a potent hallucinogen that was popular in the 1960s-1980s but is now less common. Typical doses are 20-80 micrograms and effects last 8-12 hours, including visual and sensory distortions.
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as DOCX, PDF, TXT or read online on Scribd
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Lysergide (LSD) is a semi-synthetic hallucinogen, and is one of the most

potent drugs known. Recreational use became popular between the 1960s
to 1980s, but is now less common. It is generally believed that most LSD is
produced outside Europe, but secondary preparation of dosage units by
dipping or spotting paper squares is more widespread. These dosage units
usually bear coloured designs featuring cartoon characters, geometric and
abstract motifs. LSD is related to other substituted tryptamines, and is
under international control.

Chemistry
The International Non-proprietary Name (INN) is (+)- lysergide. The
abbreviation LSD is derived from its German name
LysergSureDiethylamid (Lysergic acid diethylamide) (CAS-50-37-3).
Lysergide belongs to a family of indole alkylamines that includes numerous
substituted tryptamines such as psilocin (found in magic mushrooms)
and N,N-dimethyltryptamine (DMT). The IUPAC name for LSD is 9,10didehydro-N,N-diethyl-6-methylergoline-8-carboxamide. The (R)
stereoisomer is more potent than the (S) form.
Molecular structure

Molecular formula: C20H25N3O


Molecular weight: 323.4
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Physical form
LSD is normally produced as tartrate salt, which is colourless, odourless
and water soluble. The common street dose forms are blotters or paper
squares sheets of absorbent paper printed with distinctive designs and
perforated so they may be torn into single small (typically 7 mm) squares
each containing a single dose. Each sheet typically contains 100 or more
doses. LSD is less commonly seen as small tablets (microdots) that are
23 mm in diameter, as thin gelatine squares (window panes) or in
capsules. Solutions of LSD in water or alcohol are occasionally
encountered. LSD is light sensitive in solution, but more stable in dosage
units.
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Pharmacology
LSD was first synthesised by Albert Hoffman while working for Sandoz
Laboratories in Basel in 1938. Some years later, during a re-evaluation of
the compound, he accidentally ingested a small amount and described the
first trip. During the 1950s and 1960s, Sandoz evaluated the drug for
therapeutic purposes and marketed it under the name Delysid. It was
used for research into the chemical origins of mental illness. Recreational
use started in the 1960s and is associated with the psychedelic period.
Physical effects (e.g. dilated pupils, mild hypertension and occasionally
raised body temperature) appear first. Sensory-perceptual changes are the
outstanding features of LSD. Visual disturbances are perceived with eyes
closed or open and may consist of geometric shapes or figures in patterns.
Flashes of intense colour are seen and stable objects may appear to move
and dissolve. Cross-sensory perception (synaesthesia) such as coloured
hearing can occur where sounds such as voices or music evoke
perception of particular colours or shapes. The perception of time may
appear to slow down.
The mode of action of LSD is not well understood. It is thought to interact
with the serotonin system by binding to and activating 5
hydroxytryptamine subtype 2 receptor (5-HT2), which interferes with
inhibitory systems resulting in perceptual disturbances. It is amongst the
most potent drugs known, being active at doses from about 20
micrograms. Typical doses are now about 20 to 80 micrograms although in
the past, doses as high as 300 micrograms were common. Like other
hallucinogens, dependence does not occur.
When taken orally, the effects become apparent within about 30 minutes
and may continue for 8 to 12 hours or more. The duration and intensity of

effects are dose-dependant. The plasma half-life is about two-and-a-half


hours. Following a dose of 160 micrograms to 13 subjects, plasma
concentrations varied considerably up to 9 micrograms/L. In humans, LSD
is extensively transformed in the liver by hydroxylation and glucuronide
conjugation to inactive metabolites. Only about 1 % is excreted unchanged
in the urine in 24 hours. A major metabolite found in urine is 2oxylysergide.
Panic reactions (bad trips) may be sufficiently severe to require medical
support. Patients usually recover within a few hours but occasionally
hallucinations last up to 48 hours and psychotic states for 34 days. The
effects are greatly affected by the set (an individuals mental state) and the
setting (surroundings) in which the drug is taken. Sensory disturbances
known as flashbacks sometimes occur. Serious side effects often
attributed to LSD such as irrational acts leading to suicide or accidental
deaths, are extremely rare. Deaths attributed to LSD overdose are virtually
unknown.
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Synthesis and precursors


Methods for producing LSD are complex and require an experienced
chemist. Several methods are known, but the majority use lysergic acid as
the precursor. Lysergic acid itself is also often produced in clandestine
laboratories using ergometrine or ergotamine tartrate as the starting
material. Ergotamine occurs naturally in the ergot fungus (Claviceps
purpurea), a common parasite on rye. Depending on the method used,
other essential reagents include N,N-carbonyldi-imidazole, diethylamine or
hydrazine. Absorbent paper doses (blotters) are prepared by dipping the
paper in an aqueous alcoholic solution of the tartrate salt, or by dropping
the solution onto individual squares.
Ergometrine (also known as ergonovine), ergotamine and lysergic acid are
listed in Table I in the Annex to the United Nations 1988 Convention
Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances.
The corresponding EU legislation is set out in Council Regulation (EEC)
No 3677/90 and its amendments, which governs trade between the EU
and third countries.
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Mode of use
LSD is taken orally. Paper doses are placed on the tongue, where the drug
is rapidly absorbed. Tablets or capsules are swallowed. LSD is not
absorbed through dry skin.
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Other names
Synonyms include N,N-diethyl-lysergamide, lysergic acid diethylamide,

LSD, and LSD-25. There are many street names including acid, blotter,
dots, tabs, tickets, trips and many others related to the particular designs
on the paper dosage forms.
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Analysis
LSD may be detected in paper doses after extracting the drug into
methanol. The extract is spotted onto filter paper, dried and examined
under ultraviolet light (360 nm); LSD gives a strong blue fluorescence.
Ehrlichs reagent (p-dimethyl-aminobenzaldehyde) gives a blue/purple
colour and may be applied after thin layer chromatography. HPLC with
fluorescence detection or gas chromatography/mass spectrometry are
used for confirmation or quantification. The major ions in the mass
spectrum are m/z = 323, 221, 181, 222, 207, 72, 223 and 324. Commercial
immunoassays are available for the detection of LSD in urine at
concentrations at or above 0.5 micrograms/L.
Many ergot alkaloids can interfere with LSD analysis, e.g. ergometrine,
methylergometrine, dihydroergotamine, ergocornine, ergocristine,
methysergide, and ergotamine. LSD degrades readily, particularly in
biological specimens, unless protected from light and elevated
temperatures; it may also bind to glass containers in acidic solutions. The
only analogue of LSD to have received widespread interest is the Nmethylpropylamide of lysergic acid (LAMPA), and any analytical technique
should be capable of separating LAMPA from LSD.
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Typical purities
Because LSD is so potent, there is no need for it to be adulterated.
Laboratories rarely encounter the drug as a powder so rarely measure
purity. As mentioned earlier, the drug decomposes in light and at high
temperatures.
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Control status
LSD is listed in Schedule I of the United Nations 1971 Convention on
Psychotropic Substances.
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Prevalence
Among young adults (15- to 34-year-olds), lifetime prevalence of LSD use
varies between countries, from 0.1 % to 5.4 % (Table GPS-1, part (iii)).
Last year use of LSD in this age group ranges from 0 % to 1.7 % (Table
GPS-2, part (ii)). Lifetime prevalence of LSD (or other hallucinogen use,
excluding hallucinogenic mushrooms) among 15- to 16-year-old school
students ranged from 1 % to 5 % in the 24 EU Member States and Norway

with ESPAD surveys in 2011, with only the Czech Republic reporting a
prevalence level of 5 %.
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Street price
In 2011, the mean cost to users of a unit of LSD ranged from EUR 4.5
(Netherlands) to EUR 25 (Italy) (Table PPP-4 part (i)). The mean price of
LSD, corrected for inflation, decreased 14 % at European level 200611
(Figure PPP-2).
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Medical use
Although once used in psychotherapy, LSD has no current medical use.

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