Lysergic acid

Lysergic acid
IUPAC name	7-Methyl- 4,6,6a,7,8,9- hexahydro- indolo [4,3-fg] quinoline- 9-carboxylic acid
Other names	6-Methyl- 9,10- didehydroergoline- 8-carboxylic acid
Identifiers
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=CNC4=C3C2=CC=C4
Properties
Molecular formula	C16H16N2O2
Molar mass	268.31 g mol−1
Melting point	238 - 240 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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 or 270 Pa) 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]

Chemical structures of lysergic acid isomers

See also

• Lysergic acid diethylamide (also known as LSD)
• Lysergic acid amide (LSA/Ergine)
• Ergoline
• Lysergamides

References

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