| Record Information |
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| Version | 2.0 |
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| Creation Date | 2010-04-23 14:28:06 UTC |
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| Update Date | 2014-12-24 20:26:22 UTC |
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| Accession Number | T3D3687 |
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| Identification |
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| Common Name | Lysergic acid hydroxyethylamide |
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| Class | Small Molecule |
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| Description | Lysergic acid hydroxyethylamide (LSH) is an alkaloid of the ergoline family. Like other ergoline alkaloids, it occurs in various species of vines of the Convolvulaceae (morning glory) family and in some species of lower fungi. It is structurally is similar to LSD, with the N,N- diethylamide group replaced by an N- (1- hydroxyethyl)amide in D-lysergic acid α-hydroxyethylamide. It's effect on humans has not been thoroughly studied, but long term exposure to many ergoline alkaloids is known to cause ergotism, a disease causing convulsive and gangrenous symptoms. (7, 10) |
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| Compound Type | - Amide
- Amine
- Fungal Toxin
- Mycotoxin
- Natural Compound
- Organic Compound
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| Chemical Structure | |
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| Synonyms | | Synonym | | (S)-9,10-Didehydro-N-(1-hydroxyethyl)-6-methylergoline-8beta-carboxamide | | LSH | | Lysergamide, N-(1-hydroxyethyl)- (7CI) | | Lysergate hydroxyethylamide | | Lysergic acid alpha-hydroxyethylamide | | Lysergic acid methyl carbinolamide | | N-(alpha-Hydroxyethyl)lysergamide |
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| Chemical Formula | C18H21N3O2 |
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| Average Molecular Mass | 311.378 g/mol |
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| Monoisotopic Mass | 311.163 g/mol |
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| CAS Registry Number | 3343-15-5 |
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| IUPAC Name | N-(1-hydroxyethyl)-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide |
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| Traditional Name | N-(1-hydroxyethyl)-6-methyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide |
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| SMILES | CC(O)NC(=O)C1CN(C)C2CC3=CNC4=CC=CC(=C34)C2=C1 |
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| InChI Identifier | InChI=1S/C18H21N3O2/c1-10(22)20-18(23)12-6-14-13-4-3-5-15-17(13)11(8-19-15)7-16(14)21(2)9-12/h3-6,8,10,12,16,19,22H,7,9H2,1-2H3,(H,20,23) |
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| InChI Key | InChIKey=WYTJZJPVCDWOOI-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as lysergamides. These are amides of Lysergic acids. |
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| Kingdom | Organic compounds |
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| Super Class | Alkaloids and derivatives |
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| Class | Ergoline and derivatives |
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| Sub Class | Lysergic acids and derivatives |
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| Direct Parent | Lysergamides |
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| Alternative Parents | |
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| Substituents | - Lysergic acid amide
- Indoloquinoline
- Benzoquinoline
- Pyrroloquinoline
- Quinoline-3-carboxamide
- Quinoline
- 3-alkylindole
- Indole
- Indole or derivatives
- Isoindole or derivatives
- Aralkylamine
- Benzenoid
- Heteroaromatic compound
- Pyrrole
- Tertiary aliphatic amine
- Tertiary amine
- Secondary carboxylic acid amide
- Carboxamide group
- Amino acid or derivatives
- Azacycle
- Organoheterocyclic compound
- Carboxylic acid derivative
- Alkanolamine
- Hydrocarbon derivative
- Amine
- Organic oxygen compound
- Organopnictogen compound
- Organonitrogen compound
- Carbonyl group
- Organic nitrogen compound
- Organooxygen compound
- Organic oxide
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Exogenous |
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| Cellular Locations | |
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Solid |
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| Appearance | White powder. |
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| Experimental Properties | | Property | Value |
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| Melting Point | Not Available | | Boiling Point | Not Available | | Solubility | Not Available | | LogP | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | Deposition Date | View |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-2097000000-6da4a14beba24a1e6251 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0j4i-2090000000-a05d8a9e82d76f2915d7 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-02gn-4930000000-c444892b1c4e28132ed9 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-1079000000-545bf283cfc4c10cc7de | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-02t9-3092000000-d0f032ae06f4cb904f79 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9260000000-cef6aeaf5ae8b6bbe82e | 2016-08-03 | View Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Oral, dermal, inhalation, and parenteral (contaminated drugs). (6) |
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| Mechanism of Toxicity | Ergoline alkaloids tend to act as a group, producing complex and variable effects of partial agonism or antagonism at adrenergic, dopaminergic, and serotonergic receptors. Variables relating to these effects are influenced by the agent, dosage, species, tissue, physiological, and endocrinological state, and experimental conditions. In particular, ergoline alkaloids have been shown to have the significant affinity towards the 5-HT1 and 5-HT2 serotonin receptors, D1 and D2 dopamine receptors, and alpha-adrenergic receptors. This can result in a number of different effects, including vasoconstriction, convulsions, and hallucinations. Animal studies of LSH have shown it to have oxytocic and adrenergic blocking effects similar to ergometrine. (2, 3, 4, 5) |
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| Metabolism | Not Available |
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| Toxicity Values | LD50: 150 mg/kg (Intravenous, Mouse) (5) |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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| Uses/Sources | Lysergic acid hydroxyethylamide (LSH) is an alkaloid of the ergoline family. Like other ergoline alkaloids, it occurs in various species of vines of the Convolvulaceae (morning glory) family and in some species of lower fungi. (7) |
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| Minimum Risk Level | Not Available |
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| Health Effects | Ingestion of ergoline alkaloids is known to cause the disease ergotism. Ergotism occurs in two forms, gangrenous and convulsive, likely depending on the different kinds and amounts of ergoline alkaloids present. (1) |
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| Symptoms | Convulsive ergotism can cause painful seizures and spasms, diarrhea, paresthesias, itching, headaches, nausea and vomiting. Usually the gastrointestinal effects precede the central nervous system effects. As well as seizures there can be hallucinations and mental effects including mania or psychosis. Gangrenous ergotism causes dry gangrene as a result of vasoconstriction induced in the more poorly vascularized distal structures, such as the fingers and toes. Symptoms include desquamation, weak periphery pulse, loss of peripheral sensation, edema and ultimately the death and loss of affected tissues. (8) |
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| Treatment | Treatment for ergotism consists of vasodilators, anticoagulants and low molecular weight dextrans. If necessary, a sympathetic nerve blockade may be carried out, such as brachial plexus blockade. Temporary sedation (e.g. haloperidol) will be necessary in hallucination and diazepam is used for convulsions. There is no specific antidote. (9) |
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| Normal Concentrations |
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| Not Available |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | Not Available |
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| HMDB ID | Not Available |
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| PubChem Compound ID | 134553 |
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| ChEMBL ID | Not Available |
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| ChemSpider ID | Not Available |
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| KEGG ID | Not Available |
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| UniProt ID | Not Available |
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| OMIM ID | |
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| ChEBI ID | Not Available |
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| BioCyc ID | Not Available |
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| CTD ID | Not Available |
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| Stitch ID | Not Available |
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| PDB ID | Not Available |
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| ACToR ID | Not Available |
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| Wikipedia Link | Lysergic_acid_hydroxyethylamide |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | T3D3687.pdf |
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| General References | - Richard JL: Some major mycotoxins and their mycotoxicoses--an overview. Int J Food Microbiol. 2007 Oct 20;119(1-2):3-10. Epub 2007 Jul 31. [17719115 ]
- Mantegani S, Brambilla E, Varasi M: Ergoline derivatives: receptor affinity and selectivity. Farmaco. 1999 May 30;54(5):288-96. [10418123 ]
- Schiff PL: Ergot and its alkaloids. Am J Pharm Educ. 2006 Oct 15;70(5):98. [17149427 ]
- Kvernmo T, Hartter S, Burger E: A review of the receptor-binding and pharmacokinetic properties of dopamine agonists. Clin Ther. 2006 Aug;28(8):1065-78. [16982285 ]
- GLASSER A: Some pharmacological actions of D-lysergic acid methyl carbinolamide. Nature. 1961 Jan 28;189:313-4. [13705953 ]
- Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
- Wikipedia. Ergoline. Last Updated 2 April 2010. [Link]
- Wikipedia. Ergotism. Last Updated 6 April 2010. [Link]
- Van den Enden, E. (2004). Illustrated Lecture Notes on Tropical Medicine. [Link]
- Wikipedia. Lysergic acid hydroxyethylamide. Last Updated 4 April 2010. [Link]
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| Gene Regulation |
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| Up-Regulated Genes | Not Available |
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| Down-Regulated Genes | Not Available |
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