Names | |
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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)
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ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.001.302 |
PubChem
CID
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UNII | |
CompTox Dashboard (
EPA)
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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 [1] |
Legal status | |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
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, 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. [3]
Lysergic acid received its name as it was a product of the lysis of various ergot alkaloids. [4]
Lysergic acid is generally produced by hydrolysis [5] of natural lysergamides, but can also be synthesized in the laboratory by a complex total synthesis, for example by Robert Burns Woodward's team in 1956. [6] An enantioselective total synthesis based on a palladium-catalyzed domino cyclization reaction has been described in 2011 by Fujii and Ohno. [7] 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. [4] The biosynthetic pathway has been reconsituted in transgenic baker's yeast. [8]
Lysergic acid is a chiral compound with two stereocenters. The isomer with inverted configuration at carbon atom 8 close to the carboxyl group is called isolysergic acid. Inversion at carbon 5 close to the nitrogen atom leads to L-lysergic acid and L-isolysergic acid, respectively.
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 |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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 [1] |
Legal status | |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
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, 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. [3]
Lysergic acid received its name as it was a product of the lysis of various ergot alkaloids. [4]
Lysergic acid is generally produced by hydrolysis [5] of natural lysergamides, but can also be synthesized in the laboratory by a complex total synthesis, for example by Robert Burns Woodward's team in 1956. [6] An enantioselective total synthesis based on a palladium-catalyzed domino cyclization reaction has been described in 2011 by Fujii and Ohno. [7] 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. [4] The biosynthetic pathway has been reconsituted in transgenic baker's yeast. [8]
Lysergic acid is a chiral compound with two stereocenters. The isomer with inverted configuration at carbon atom 8 close to the carboxyl group is called isolysergic acid. Inversion at carbon 5 close to the nitrogen atom leads to L-lysergic acid and L-isolysergic acid, respectively.