Lysergic acid
| D-Lysergic acid | |
|---|---|
| Chemical structure of 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 |
| 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=[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, 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 crystallizes 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 [1].
See also
- LSD
- Lysergic acid amide (LSA/Ergine)
- Ergoline
- Lysergamides