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Revision as of 20:17, 9 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:Wi← Previous edit Latest revision as of 22:50, 30 December 2024 edit undoMfernflower (talk | contribs)Extended confirmed users7,828 editsNo edit summary 
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{{Short description|Precursor for a range of ergoline alkaloids produced by the ergot fungus}}
{{Distinguish|Lysergic acid diethylamide}}
{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 443927630
| Watchedfields = changed
⚫ | ImageFile = lysergic_acid_chemical_structure.png
⚫ | verifiedrevid = 443929247
⚫ | ImageFile = lysergic_acid_chemical_structure.svg
| ImageSize = 180px | ImageSize = 180px
| ImageClass = skin-invert
| ImageFile1 = Lysergic_acid.png | ImageFile1 = Lysergic_acid.png
| ImageSize1 =181px | ImageSize1 = 180px
| IUPACName = 7-Methyl- 4,6,6''a'',7,8,9- hexahydro- indolo quinoline- 9-carboxylic acid | IUPACName = 6-Methyl-9,10-didehydroergoline-8β-carboxylic acid
| OtherNames = 6-Methyl- 9,10- didehydroergoline- 8-carboxylic acid | SystematicName = (5''R'',8''R'')-7-Methyl-4,6,6a,7,8,9-hexahydroindoloquinoline-9-carboxylic acid
| OtherNames =
| Section1 = {{Chembox Identifiers |Section1= {{Chembox Identifiers
| IUPHAR_ligand = 139
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6461 | ChemSpiderID = 6461
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZAGRKAFMISFKIO-QMTHXVAHSA-N | StdInChIKey = ZAGRKAFMISFKIO-QMTHXVAHSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 82-58-6 | CASNo = 82-58-6
| UNII_Ref = {{fdacite|changed|FDA}}
| CASOther = <br/>, <br/>, <br/>, <br/>, <br/>
| PubChem = | UNII = ITO20DAO7J
| PubChem = 6717
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 6604 | ChEBI = 6604
| SMILES = O=C(O)3/C=C2/c4cccc1c4c(cn1)C2N(C3)C | SMILES = CN1C(C=C21CC3=CNC4=CC=CC2=C34)C(=O)O
}} }}
| Section2 = {{Chembox Properties |Section2= {{Chembox Properties
| C=16|H=16|N=2|O=2 | C= 16|H= 16|N= 2|O= 2
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = 238 - 240 °C | MeltingPtC = 238 to 240
| MeltingPt_notes =
| BoilingPt = | BoilingPt =
| Solubility = }} | Solubility =
| pKa = p''K''<sub>a1</sub> = 7.80, p''K''<sub>a2</sub> = 3.30 <ref>{{cite book|last=Brown |first=H. C. |display-authors=etal |editor1-last=Braude |editor1-first=E. A. |editor2-first=F. C. |editor2-last=Nachod |title=Determination of Organic Structures by Physical Methods |publisher=Academic Press |location=New York, NY |date=1955}}</ref>}}
| Section3 = {{Chembox Hazards |Section3= {{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = }} | AutoignitionPt =
}}
|Section4={{Chembox Legal status
| legal_AU =
| legal_BR = D1
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-15 |publisher=] |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_US =
| legal_UK =
| legal_UN =
}}
}} }}


'''Lysergic acid''', also known as '''{{sc|D}}-lysergic acid''' and '''(+)-lysergic acid''', is a precursor for a wide range of ] ]s that are produced by the ] fungus and found in the seeds of '']'' (]), and '']'' species (], ], ]).
'''Lysergic acid''', also known as '''<small>D</small>-lysergic acid''' and '''(+)-lysergic acid''', is a precursor for a wide range of ] alkaloids that are produced by the ] fungus and some plants. ]s of lysergic acid, ], are widely used as ] and as ]s (]). Lysergic acid is usually produced by ] of lysergamides, but can also be synthesized in the laboratory by a complex ]. Lysergic acid monohydrate crystallizes in very thin hexagonal leaflets when recrystallized from water. Lysergic acid monohydrate, when dried (140 °C at {{convert|2|mmHg|Pa|abbr=on|disp=or}}) forms anhydrous lysergic acid. Lysergic acid is a ] compound with two ]s. The ] with inverted configuration at carbon atom 8 close to the ] group is called '''isolysergic acid'''. Inversion at carbon 5 close to the ] atom leads to '''<small>L</small>-lysergic acid''' and '''<small>L</small>-isolysergic acid''', respectively. Lysergic acid is listed as a Table I precursor under the ].<ref>, International Narcotics Control Board </ref>


]s of lysergic acid, ], are widely used as ]s and as ]s, e.g. ] (LSD). Lysergic acid is listed as a Table I precursor under the ].<ref>{{cite web|url=http://www.incb.org/pdf/e/list/red.pdf |title=List of Precursors and Chemicals Frequently Used in the Illicit Manufacture of Narcotic Drugs and Psychotropic Substances Under International Control |url-status=dead |archive-url=https://web.archive.org/web/20080227224025/http://www.incb.org/pdf/e/list/red.pdf |archive-date=2008-02-27 |publisher=International Narcotics Control Board}}</ref>
⚫ ]<br clear="left"/>


The name Lysergic acid comes from the fact that the this ] was first made by ] of various ].<ref name=Schiff>{{cite journal|journal=Am. J. Pharm. Educ.|date=Oct 15, 2006|volume=70|issue=5|pages=98|title=Ergot and its alkaloids|last=Schiff|first=P. L.|pmid=17149427|pmc=1637017|doi=10.5688/aj700598}}</ref>
⚫ == See also ==


== Synthesis ==
=== Laboratory ===
Lysergic acid is generally produced by ]<ref>{{cite journal|journal=J. Biotechnol.|date=Nov 17, 2001|volume=84|issue=1|pages=63–6|title=Hydrolysis of lysergamide to lysergic acid by ''Rhodococcus equi'' A4|last1=Martínková |first1=L. |last2=Kren |first2=V. |last3=Cvak |first3=L. |last4=Ovesná |first4=M. |last5=Prepechalová |first5=I.|doi=10.1016/s0168-1656(00)00332-1|pmid=11035188}}</ref> of natural lysergamides, but can also be synthesized in the laboratory by a complex ], for example by ]'s team in 1956.<ref>{{cite journal|title=The Total Synthesis of Lysergic Acid|journal=J. Am. Chem. Soc.|volume=78|issue=13|pages=3087–3114|year=1956|first=Edmund C. |last1=Kornfeld|first2=E. J. |last2=Fornefeld|first3=G. Bruce |last3=Kline|first4=Marjorie J. |last4=Mann|first5=Dwight E. |last5=Morrison|first6=Reuben G. |last6=Jones|first7=R. B. |last7=Woodward|doi=10.1021/ja01594a039}}</ref> An ] total synthesis based on a ]-catalyzed domino ] has been described in 2011 by Fujii and Ohno.<ref name=ohno1>{{cite journal|first1=S. |last1=Inuki |first2=A. |last2=Iwata |first3=S. |last3=Oishi |first4=N. |last4=Fujii |first5=H. |last5=Ohno |title=Enantioselective Total Synthesis of (+)-Lysergic Acid, (+)-Lysergol, and (+)-Isolysergol by Palladium-Catalyzed Domino Cyclization of Allenes Bearing Amino and Bromoindolyl Groups |journal=J. Org. Chem. |date=2011 |volume=76 |issue=7 |pages=2072–2083 |doi=10.1021/jo102388e|pmid=21361331 }}</ref> Lysergic acid monohydrate crystallizes in very thin hexagonal leaflets when recrystallized from water. Lysergic acid monohydrate, when dried (140&nbsp;°C at {{convert|2|mmHg|Pa|abbr=on|disp=or}}) forms anhydrous lysergic acid.


=== Biosynthesis ===
* ]
The biosynthetic route is based on the ] of the amino acid ] with ] (] derived from 3''R''-]) giving 4-dimethylallyl-{{sc|L}}-tryptophan which is ''N''-methylated with ]. Oxidative ring closure followed by decarboxylation, reduction, cyclization, oxidation, and allylic ] yields {{sc|D}}-(+)-lysergic acid.<ref name=Schiff /> The biosynthetic pathway has been reconsituted in transgenic baker's yeast.<ref name=Wong2022>{{cite journal|title=Reconstituting the complete biosynthesis of D-lysergic acid in yeast|journal=Nature Communications|year=2022|volume=13|issue=1|page=712|doi=10.1038/s41467-022-28386-6|pmid=35132076|pmc=8821704|bibcode=2022NatCo..13..712W |last1=Wong |first1=Garrett |last2=Lim |first2=Li Rong |last3=Tan |first3=Yong Quan |last4=Go |first4=Maybelle Kho |last5=Bell |first5=David J. |last6=Freemont |first6=Paul S. |last7=Yew |first7=Wen Shan }}</ref>
* ] (LSA/Ergine)

⚫ * ]
==Isomers==
Lysergic acid is a ] compound with two ]s. The ] with inverted configuration at carbon atom 8 close to the ] group is called '''isolysergic acid'''. Inversion at carbon 5 close to the ] atom leads to '''{{sc|L}}-lysergic acid''' and '''{{sc|L}}-isolysergic acid''', respectively.

⚫ ]{{clear|left}}

== Legality ==

In the United States, Lysergic acid and Lysergic acid amide are Schedule III substances.<ref>https://www.ecfr.gov/current/title-21/chapter-II/part-1308/subject-group-ECFRf62f8e189108c4d/section-1308.13</ref>

⚫ ==See also==
⚫ * ]
* ] * ]


==References== ==References==
{{reflist}} {{Reflist|30em}}
{{Wiktionary|lysergic|lysergic acid}}


{{Ergolines}} {{Ergolines}}


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