| D-Lysergic acid
|
| Chemical name
| 6-Methyl-9,10-didehydro-ergoline-8-carboxylic acid
or
7-methyl-4,6,6a,7,8,9-
hexahydro-indolo*
quinoline-9-carboxylic acid
|
| Chemical formula
| C16H16N2O2
|
| Molecular mass
| 268.31 g/mol
|
| Melting point
| 238 - 240 °C
|
| pI
| ?
|
| Properties
| Prisms from methanol, dec 242°.
|
| CAS number
| 82-58-6, 478-95-5,
6915-32-8, 23953-76-6,
68985-97-7, 68985-98-8
|
| SMILES
| O=*(O)*1CN(C)
*(C2=C1)(*)CC3=C
NC4=C3C2=CC=C4
|
Lysergic acid, also known as
D-lysergic acid and
(+)-lysergic acid, is a precursor for a wide range of
ergoline alkaloids that are produced by the
ergot fungus and some plants.
Amides of lysergic acid, commonly called lysergamides, are widely used as
pharmaceuticals and as
psychedelic drugs (
LSD). Lysergic acid is usually produced by
hydrolysis of lysergamides, but can also be synthesized in the laboratory by a complex
total synthesis. Lysergic acid monohydrate crystalizes in very thin hexagonal leaflets when recrystallized from water. Lysergic acid monohydrate, when dried (140 °C at 2 mmHg) forms anhydrous lysergic acid. Lysergic acid is a
chiral compound with two
stereocenters. The
isomer with inverted configuration at carbon atom 8 close to the
carboxy group is called
isolysergic acid. Inversion at carbon 5 close to the
nitrogen atom leads to
L-lysergic acid and
L-isolysergic acid, respectively. Lysergic acid is listed as a Table I precursor under the
United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances *.
See also
Lysergamides
Lysergsäure | Acide lysergique | Kwas lizergowy | Lysergsyra
"Lysergic acid"