| 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[4,3-fg]
quinoline-9-carboxylic acid
|
| Chemical formula
| C16H16N2O2
|
| Molecular mass
| 268.31 g/mol
|
| Melting point
| 238 - 240 °C
|
| CAS number
| 82-58-6, 478-95-5,
6915-32-8, 23953-76-6,
68985-97-7, 68985-98-8
|
| SMILES
| O=[C@](O)[C@H]1CN(C)
[C@](C2=C1)([H])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 hallucinogenic drugs (LSD). Lysergic acid is usually produced by hydrolysis of lysergamides, but can also be synthesized in the laboratory by a complex total syntheses. 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.
See also
