Lysergic acid

Lysergic acid
Names
	IUPAC name 6-Methyl-9,10-didehydroergoline-8β-carboxylic acid
	Systematic IUPAC name (5R,8R)-7-Methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxylic acid
Identifiers
CAS Number	82-58-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:6604 ;
ChemSpider	6461 ;
ECHA InfoCard	100.001.302
IUPHAR/BPS	139;
PubChem CID	6717;
UNII	ITO20DAO7J ;
CompTox Dashboard (EPA)	DTXSID60904515 ;
	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 Key: ZAGRKAFMISFKIO-QMTHXVAHSA-N ; 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 CN1C[C@@H](C=C2[C@H]1CC3=CNC4=CC=CC2=C34)C(=O)O;
Properties
Chemical formula	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	BR: Class D1 (Drug precursors);
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) 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 Argyreia nervosa (Hawaiian baby woodrose), and Ipomoea species (morning glories, ololiuhqui, 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]

The name "lysergic acid" comes from the fact that it is a carboxylic acid, and it was first made by hydrolysis of various ergot 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.

[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.

[Schiff-4] 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.

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