Lysergic acid

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 Turbina corymbosa (ololiuhqui), Argyreia nervosa (Hawaiian baby woodrose), and Ipomoea tricolor (morning glories, tlitliltzin).

Not to be confused with Lysergic acid diethylamide.
Lysergic acid
Names
IUPAC name
6-Methyl-9,10-didehydroergoline-8β-carboxylic acid
Systematic IUPAC name
(6aR,9R)-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

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.

Lysergic acid received its name as it was a product of the lysis of various ergot alkaloids.

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