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
'. /
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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
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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
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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]