Precursor for a range of ergoline alkaloids produced by the ergot fungus
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
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
C 16 H 16 N 2 O 2
Molar mass
268.316 g·mol−1
Melting point
238 to 240 °C (460 to 464 °F; 511 to 513 K)
Acidity (pK a )
pK a1 = 7.80, pK a2 = 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).
Chemical compound
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 lys is of various erg ot alkaloids.[ 4]
^ 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.
^ 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 .
^ "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.
^ Schiff, P. L. (Oct 15, 2006). "Ergot and its alkaloids" . Am. J. Pharm. Educ . 70 (5): 98. doi :10.5688/aj700598 . PMC 1637017 . PMID 17149427 .