Lysergic acid

Lysergic acid
Names
IUPAC name
6-Methyl-9,10-didehydroergoline-8β-carboxylic acid
Systematic IUPAC name
(5R,8R)-7-Methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.302
UNII
  • InChI=1S/C16H16N2O2/c1-18-8-10(16(19)20)5-12-11-3-2-4-13-15(11)9(7-17-13)6-14(12)18/h2-5,7,10,14,17H,6,8H2,1H3,(H,19,20)/t10-,14-/m1/s1 Y
    Key: ZAGRKAFMISFKIO-QMTHXVAHSA-N Y
  • InChI=1/C16H16N2O2/c1-18-8-10(16(19)20)5-12-11-3-2-4-13-15(11)9(7-17-13)6-14(12)18/h2-5,7,10,14,17H,6,8H2,1H3,(H,19,20)/t10-,14-/m1/s1
    Key: ZAGRKAFMISFKIO-QMTHXVAHBD
  • CN1C[C@@H](C=C2[C@H]1CC3=CNC4=CC=CC2=C34)C(=O)O
Properties
C16H16N2O2
Molar mass 268.316 g·mol−1
Melting point 238 to 240 °C (460 to 464 °F; 511 to 513 K)
Acidity (pKa) pKa1 = 7.80, pKa2 = 3.30
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
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 found in the seeds of Argyreia nervosa (Hawaiian baby woodrose), and Ipomoea species (morning glories, ololiuhqui, tlitliltzin).

Amides of lysergic acid, lysergamides, are widely used as pharmaceuticals and as psychedelic drugs, e.g. lysergic acid diethylamide (LSD). Lysergic acid is listed as a Table I precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances.

The name Lysergic acid comes from the fact that it is a carboxylic acid, and it was first made by hydrolysis of various ergot alkaloids.

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