Index Merck sur le LSD

Monograph Number: 5654
Title: Lysergide
CAS Registry Number: 50-37-3
CAS Name: 9,10-Didehydro-N,N-diethyl-6-methylergoline-8b-carboxamide
Additional Names: N,N-diethyl-D-lysergamide; D-lysergic acid diethylamide; LSD; LSD-25; lysergsäure diethylamid
Molecular Formula: C20H25N3O
Molecular Weight: 323.43.
Percent Composition: C 74.27%, H 7.79%, N 12.99%, O 4.95%
Literature References: Microbial formation by Claviceps paspali over the hydroxyethylamide: Arcamone et al., Proc. Roy. Soc. (London) 155B, 26 (1961). Partial synthesis: Stoll, Hofmann, Helv. Chim. Acta 26, 944 (1943); 38, 421 (1955). Industrial prepn: Pioch, US 2736728; Garbrecht, US 2774763 (both 1956 to Lilly); Patelli, Bernardi, US 3141887 (1964 to Farmitalia). Isotope-labeled LSD: Stoll et al., Helv. Chim. Acta 37, 820 (1954). Toxicity data: E. Rothlin, Ann. N.Y. Acad. Sci. 66, 668 (1957). Review: Hoffer, Clin. Pharmacol. Ther. 6, 183 (1965). Book: The Use of LSD in Psychotherapy and Alcoholism, H. A. Abramson, Ed. (Bobbs-Merrill, Indianapolis, 1967) 697 pp.
Properties: Pointed prisms from benzene, mp 80-85°. [a]D20 +17° (c = 0.5 in pyridine). uv max (ethanol): 311 nm (E1%1cm 257). LD50 in mice, rats, rabbits (mg/kg): 46, 16.5, 0.3 i.v. (Rothlin).
Melting point: mp 80-85°
Optical Rotation: [a]D20 +17° (c = 0.5 in pyridine)
Absorption maximum: uv max (ethanol): 311 nm (E1%1cm 257)
Toxicity data: LD50 in mice, rats, rabbits (mg/kg): 46, 16.5, 0.3 i.v.

Derivative Type: D-Tartrate
Molecular Formula: C46H64N6O10
Molecular Weight: 861.03.
Percent Composition: C 64.17%, H 7.49%, N 9.76%, O 18.58%
Properties: Solvated, elongated prisms from methanol, mp 198-200°. [a]D20 +30°. Soluble in water.
Melting point: mp 198-200°
Optical Rotation: [a]D20 +30°

NOTE: This is a controlled substance (hallucinogen): 21 CFR, 1308.11.
Use: In biochemical research as antagonist to serotonin. Has been used experimentally as adjunct in study and treatment of mental disorders.