Newsgroups: alt.drugs Distribution: world Subject: From the Merck Manual -- LSD references, etc Keywords: LSD, Lysergic Acid Amide, Lysergic Acid Summary: A couple of pages of copywrite infringement From the 11th Edition of the Merck manual, the "Centennial Edition" no less: [perhaps something to drop in the FAQ?] 5505. Lysergamide. 9,10-Didehydro-6-methylergoline- 8beta-carboxamide; lysergic acid amide; ergine. C16H17N3O; mol wt 267.32. C 71.88%, H 6.41%, N 15.72%, O 5.99%. Isoln from _Rivea_corymbosa_(L.) and from _Ipomoea_tricolor_ Cav., _Convolvulaceae_: Hofmann, Tscherter, _Experientia_ 16, 414 (1964). Prepn from lysergic acid hydrazide: Ainsworth, U.S. pat. 2,756,235 (1956 to Lilly); from lysergic acid and phosgene-dimethylformamide complex: Patelli, Bernardi, U.S. pat. 3,141,887 (1964 to Farmitalia). Microbiological production: Rutschmann, Kobel, U.S. pat. 3,219,545 (1965 to Sandoz). H. CONH2 '. / / \ / \ || | || N /\\ /\ / \ / \\ / \ / CH3 || | | \ || | | H \ // \ / \// \/ | || | || HN------- Prisms from methanol. dec 242deg. [alpha](5461)(20) + 15% (c = 0.5 in pyridine). Methanesulfonate, C7H21N3O4S, prisms from methanol + acetone, dec 232deg. Note: This is a controlled substance (depressant) listed in the U.S. code of Federal Regulations, Title 21 Part 1308.13 (1987). 5506. Lysergic Acid. 9,10-Didehydro-6-methylergoline- 8-carboxylic acid. C16H16N2O2; mol wt 268.32. C 71.62%, H 6.01%, N 10.44%, O 11.93%. Lysergic acid and isolyser- gic acid are the main cleavage products formed on alkaline hydrolysis of the alkaloids which are characteristic of ergot. Jacobs, Craig et al., _J._Biol._Chem._ 104, 547 (1934); 125, 289 (1938); 130, 399 (1939); 145, 487 (1942); _J._Org._Chem._ 10, 76 (1945). High-yield production by _Claviceps_paspali_: Arcamone et al., _Proc._Roy._Soc._ (London), _Ser._B_, 155, 26 (1961). total synthesis: Kornfeld et al., _J._Am._Chem._Soc._ 76, 5256 (1954); 78, 3087 (1956); M. Julia et al., _Tetrahedron_ _letters_ 1969, 1569; V.W. Armstrong et al., ibid. 1976, 4311; W. Oppolzer et al., _Helv._Chem._Acta_ 64, 478 (1981); R. Ramage et al., _Tetrahedron_ 37, Suppl. 9, 157 (1981); J. Rebek, D.F. Tai, _Tetrahedron_Letters_ 24, 859 (1983). Ste- reochemistry: Stoll et al., _Helv._Chem._Acta 37, 2039 (1954); Stenlake, _J._Chem._Soc._ 1955, 1626; Leeman, Fabbri, _Helv._ _Chim._Acta_ 42, 2696 (1959). Absolute configuration: Stad- ler, Hoffman, ibid. 45, 2005 (1962). H. COOH '. / / \ / \ || | || N /\\ /\ / \ / \\ / \ / CH3 || | | \ || | | H \ // \ / \// \/ | || | || HN------- Haxagonal scales, plates with one or two moles H20 from water, mp 240deg (dec). [alpha](D)(20) + 40deg (c = 0.5 in pyridine). Behaves as an acid and base, pKa 3.44, pKb 7.68. Moder- ately sol in pyridine. Sparingly sol in water and in neutral organic solvents; sol in NaOH, NH4OH, Na2CO3, and HCL solns. Slighly sol in dil H2SO4. Methyl ester, thin leaflets from benzene, mp 168deg. Note: This is a controlled substance (depressant) listed in the U.S. code of Federal Regulations, title 21 Part 1308.13 (1987). 5507. Lysergide. 9,10-Didehydro-N,N-diethyl-6-meth- ylergoline-8beta-carboxamide; N,N-diethyl-D-lysergamide; D- lysergic acid diethylamide; LSD; LSD-25; Lysergsaure Di- ethylamid. C20H25N3O; mol wt 323.42. C 74.27%, H 7.79%, N 12.99%, O 4.95%. Microbal formation by _Claviceps_pas- pali_ 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; Garbrecht, U.S. pats. 2,736,728; 2,774,763 (both 1956 to Lilly); Patelli, Bernardi, U.S. pat. 3,141,887 (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: Hof- fer, _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. / C2H5 H. CON '. / \ C2H5 / \ / \ || | || N /\\ /\ / \ / \\ / \ / CH3 || | | \ || | | H \ // \ / \// \/ | || | || HN------- Pointed prisms from benzene, mp 80-85 degs. [alpha](D)(20) + 17deg (c = 0.5 in pyridine). uv max (ethanol): 311 nm (E(1 cm)(1%) 257). LD50 in mice, rats, rabbits (mg/kg): 46, 16.5, 0.3 i.v. (Rothlin). D-Tartrate, C46H64N6O10, solvated, elongated prisoms from methanol, mp 198-200deg. [alpha](D)(20) + 30 deg. Soluble in water. Caution: This is a controlled substance (hallucinogen) listed in the U.S. Code of Federal Regulations, Title 21 Part 1308.11 (1987). USE: In biochemical research as an antagonist to serotonin. Has been used experimentally as adjunct in study and treat- ment of mental disorders. NOTES: Not guaranteed to be free from typos. Underlines are supposed to be italic (ie book/journal titles, etc) Alpha, beta, and deg are the greek letters and the degree symbol [alpha](D)(20) means a greek letter in [] followed by a subscript and then a superscript (I don't know *WHAT* this actually is) The chemical structures are almost exactly what the Merck manual has drawn. Almost nothing was lost in the conversion to ASCII. [if you wanted to get really technical, the lower hydrogen atom in all of the structures should be coming out, and have a thick line]