Lysergic acid

Lysergic acid

Names
IUPAC name 7-Methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxylic acid
Other names 6-Methyl-9,10-didehydroergoline-8-carboxylic acid
Identifiers
CAS Number	82-58-6 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:6604 Y
ChemSpider	6461 Y
ECHA InfoCard	100.001.302
IUPHAR/BPS	139
UNII	ITO20DAO7J N
InChI 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
SMILES O=C(O)[C@@H]3/C=C2/c4cccc1c4c(cn1)C[C@H]2N(C3)C
Properties
Chemical formula	C16H16N2O2
Molar mass	268.32 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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (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 Turbina corymbosa (ololiuhqui), Argyreia nervosa (Hawaiian Baby Woodrose), and Ipomoea tricolor (morning glories, tlitliltzin). Amides of lysergic acid, lysergamides, are widely used as pharmaceuticals and as psychedelic drugs (LSD). Lysergic acid received its name as it was a product of the lysis of various ergot alkaloids.

Lysergic acid is generally produced by hydrolysis of natural lysergamides, but can also be synthesized in the laboratory by a complex total synthesis for example by Woodward's team in 1956. An enantioselective total synthesis based on a palladium catalyzed domino cyclization reaction has been described in 2011 by Fujii and Ohno. 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. The biosynthetic route is based on the alkylation of the amino acid tryptophan with dimethylallyl diphosphate (isoprene derived from 3R-mevalonic acid) giving 4-dimethylallyl-L-tryptophan which is N-methylated with S-adenosyl-L-methionine. Oxidative ring closure followed by decarboxylation, reduction, cyclization, oxidation, and allylic isomerization yields D-(+)-lysergic acid.