Lysergic acid

Encyclopedia : L : LY : LYS : Lysergic acid

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@HΣCN(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 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 [link].

Lysergic acid

See also