From: [d--e] at [unislc.slc.unisys.com] (Dale Clark) Subject: LSD Date: Mon, 14 Jun 1993 14:54:23 -0600 (MDT) ---------------------------------- LYSERGIC ACID DIETHYLAMIDE ---------------------------------- GENERAL INFO ------------ 9,10-Didehydro-N,N-diethyl-6-methylergoline-8(beta)-carboxamide; 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. STRUCTURE --------- C2 H5 \ ----- NOC / \\ / \ || | C2 H5 ----- ----- // / \\ / \-----\ | | | NH \ / \ / | - N - ------------- | CH3 COMMERCIAL DRUG NAMES --------------------- Delysid, LSD, LSD-25, Lysergide, Lysergaure Diethylamid. LD-50 ---- I.V. in mice, rats, rabbits: 46, 16.5, 0.3 mg/kg. ACTIONS ------- 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 No evidence of physical dependence can be detected when the drug is abruptly withdrawn.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. DRUG INTERACTIONS ----------------- No reliable citations are available on interaction dangers. CREATION PROCESS ---------------- 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. CHEMICAL COMMERCIAL USE / HAZARDS -------- ------------------------ acetonitrile Pharmaceuticals, solvent, extraction of vegetable oils. TOXIC / FLAMMABLE / HIGH HAZARD chloroform Variety of industrial uses. TOXIC / FLAMMABLE diethylamine Rubber chemicals, textiles, dye, solvent pharmaceuticals, electroplating, corrosion inhibitor. TOXIC / FLAMMABLE. diethylformamide Solvent for vinyl resins, orlon synthesis, organic preparations. TOXIC / FLAMMABLE. ergotamine tartrate Pharmaceutical compounding. lysergic acid Medical research. sulfur trioxide Photographic developer, explosives manufacture, detergents, solor-energy collectors, organic synthesis. CORROSIVE / HIGH HAZARD