Lysergic acid

Source: Wikipedia, the free encyclopedia.
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 Edit this at Wikidata
IUPHAR/BPS
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 checkY
    Key: ZAGRKAFMISFKIO-QMTHXVAHSA-N checkY
  • 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 [1]
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 checkY☒N ?)

Lysergic acid, also known as D-lysergic acid and (+)-lysergic acid, is a precursor for a wide range of

tlitliltzin
).

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]

Synthesis

Laboratory

Lysergic acid is generally produced by

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.

Biosynthesis

The biosynthetic route is based on the

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]

Isomers

Lysergic acid is a

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.

Chemical structures of lysergic acid isomers

See also

References

  1. ^ Brown, H. C.; et al. (1955). Braude, E. A.; Nachod, F. C. (eds.). Determination of Organic Structures by Physical Methods. New York, NY: Academic Press.
  2. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
  3. ^ "List of Precursors and Chemicals Frequently Used in the Illicit Manufacture of Narcotic Drugs and Psychotropic Substances Under International Control" (PDF). International Narcotics Control Board. Archived from the original (PDF) on 2008-02-27.
  4. ^
    PMID 17149427
    .
  5. PMID 11035188
    .
  6. doi:10.1021/ja01594a039
    .
  7. PMID 21361331
    .
  8. PMID 35132076
    .
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