LYSERGIC ACID DIETHYLAMIDE

N,N-diethyl-D-lysergamide;  D-lysergic acid diethylamide.
C20 H25 N3 O.  US pat. 2,736,728; 2,774,763 (both in 1956 to Lilly);
3,141,887 (1964 to Farmitalia).  First developed by Hoffman 1943.
Melting point 80-85F.  Soluble in water.


              C2 H5
                  \                   -----
	           NOC               /    \\
                  /   \             ||      |
	      C2 H5     -----   -----     //
                       /    \\ /     \-----\
                      |       |       |     NH
                       \     / \     /      |
                        - N -   -------------

Delysid, LSD, LSD-25, Lysergide, Lysergaure Diethylamid.

I.V. in mice, rats, rabbits: 46, 16.5, 0.3 mg/kg.

LSD is a potent synthetic hallucinogenic drug related structurally
to several other drugs (e.g. bufotenine, psilocybin, harmine,
and ibogaine).  All of these drugs block the action of serotonin
(the indole amine transmitter of nerve impulses) in the brain.
After administration, LSD can be absorbed readily from any mucosal
surface, including the ear, and acts within 30 to 60 minutes.
Effects last for 8 to 10 hours; occasionally some effects persist
for several days. Symptoms include widely dilated pupils, lower
temperature, goose bumps, increased blood sugar, and rapid heartbeat.
Chemically, LSD is an amine alkaloid resembling ergonovine and has
oxytocic action but with only slight vasoconstrictive effect.

LSD is induces a state of excitation of the CNS and central autonomic
hyperactivity, manifested by changes in mood (usually euphoric,
sometimes depressive) and perception.  True hallucinations
apparently rarely occur.  Psychic dependence on hallucinogens
varies greatly but usually is not intense.  No evidence of physical
dependence can be detected when the drug is abruptly withdrawn.
A high degree of tolerance to LSD develops and disappears rapidly.
Individuals tolerant to LSD are cross-tolerant to other hallucinogens.
The usual preferred dose ranges between 200 and 300 micrograms.

Chief dangers to the individual are the psychologic effects and
impairment of judgment, which can lead to dangerous decision
making and accidents. Some persons, especially among those who
are chronic or repeated users of hallucinogenic drugs, and
particularly with the use of LSD, may experience drug effects
after they have discontinued use of the drug.  Referred to
as "flashbacks" these episodes most commonly consist of
visual illusions but can include distortions of virtually any
sensation.  Such sensations can be precipitated by the
use of marijuana, alcohol, or barbiturates, by stress or
fatigue, or for no apparent reason.  The mechanisms which
produce flashbacks are not known, but they tend to subside
over a period of 6 months to a year.

Physically, none of the drug's toxic effects damage other organs,
and even massive overdoses do not prove fatal (this is not true
of the more chemically toxic hallucinogens such as MDA or DOM).
Experts are agreed that LSD causes no genetic abnormalities
or congenital malformations, even in individuals who have used
the drug for extended periods of time.  Research projects are
conducted under the supervision of the National Institute of
Mental Health, and black market LSD accounts for much of the
remaining manufacturing and use of the drug.

No reliable citations are available on interaction dangers.

LSD can be derived from the ergot alkaloids such as ergonovine,
principal constituents of ergot, the grain deformity and toxic
infectant of flour caused by the fungus of grasses, Claviceps
purpurea. The microbial formation occurs over the hydroxyethylamide.

LSD is produced by an anhydrous (water free) reaction between
lysergic acid, trifluoroacetic acid, acetonitrile, and
diethylamine.  The reaction time for the entire process requires
from 2 to 3 days.  

Lysergic acid is a psychomimetic under government control.  Lysergic
acid and isolysergic acid are the main cleavage products formed on
alkaline hydrolysis of the alkaloids which are characteristic of
ergot. Morning-glory seeds can be used as a source for lysergic acid,
1 kilogram (2.2 pounds) yields approximately 25 grams of lysergic acid
amide which can be made to yield more than three grams of LSD.

A solution of the mixed anhydride of d-lysergic acid (the levo [left]-
rotating form is almost completely inactive and therefore useless
as a starting material) and trifluoroacetic acid in 200 ml. of 
acetonitrile is obtained by reacting 5.36 grams of d-lysergic acid 
and 8.82 grams of trifluoroacetic anhydride.  The mixture must be
carefully handled so it doesn't pick up water from the air.  Next,
almost any diethylamine compound is dissolved in more acetonitrile and
the two solutions are mixed.

For all of these processes, the vessels must be stoppered with a
water-absorbing salt such as calcium chloride to keep moisture out.
However, after the initial mixture has reacted for 3 hours, water is
deliberately added and it is shaken.  Then, a solvent such as chloroform
is added.  The chloroform and water layers will separate, with
nearly all of the LSD being in the chloroform layer.  Pouring the
LSD/chloroform mixture through a tube full of aluminum oxide will
separate the two and the LSD will remain in the tube.

--------			------------------------
acetonitrile			Pharmaceuticals, solvent, extraction 
				of vegetable oils.

chloroform			Variety of industrial uses.

diethylamine			Rubber chemicals, textiles, dye, solvent
				pharmaceuticals, electroplating,
				corrosion inhibitor.

diethylformamide		Solvent for vinyl resins, orlon synthesis,
				organic preparations.

ergotamine tartrate		Pharmaceutical compounding.

lysergic acid			Medical research.

sulfur trioxide			Photographic developer, explosives
				manufacture, detergents, solor-energy
				collectors, organic synthesis.