| Record Information |
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| Version | 2.0 |
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| Creation Date | 2010-04-23 19:56:58 UTC |
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| Update Date | 2014-12-24 20:26:22 UTC |
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| Accession Number | T3D3688 |
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| Identification |
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| Common Name | Ergocristine |
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| Class | Small Molecule |
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| Description | Ergocristine 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. Ergocristine is one of 3 similar peptides referred to as ergotoxine alkaloids, the other two being ergocryptine and ergocornine. Ergotoxines prepared into their hihydroergotoxine mesylates, commonly known as ergoloid mesylates, are used in the symptomatic therapy of age-related dementia. Long term exposure to some ergoline alkaloids can cause ergotism, a disease causing convulsive and gangrenous symptoms. (6, 3) |
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| Compound Type | - Amide
- Amine
- Ether
- Fungal Toxin
- Mycotoxin
- Natural Compound
- Organic Compound
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| Chemical Structure | |
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| Synonyms | | Synonym | | 12'-Hydroxy-2'-(1-methyl-ethyl)-5'-(phenylmethyl)ergotaman-3'6'18-trione | | 2-Hydroxy-2-[1-methylethyl]-5-[phenylmethyl]ergotaman-3,6,18-trione |
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| Chemical Formula | C35H39N5O5 |
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| Average Molecular Mass | 609.715 g/mol |
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| Monoisotopic Mass | 609.295 g/mol |
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| CAS Registry Number | 511-08-0 |
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| IUPAC Name | N-[7-benzyl-2-hydroxy-5,8-dioxo-4-(propan-2-yl)-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl]-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-{7-benzyl-2-hydroxy-4-isopropyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.0²,⁶]dodecan-4-yl}-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(C)C1(NC(=O)C2CN(C)C3CC4=CNC5=CC=CC(=C45)C3=C2)OC2(O)C3CCCN3C(=O)C(CC3=CC=CC=C3)N2C1=O |
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| InChI Identifier | InChI=1S/C35H39N5O5/c1-20(2)34(37-31(41)23-16-25-24-11-7-12-26-30(24)22(18-36-26)17-27(25)38(3)19-23)33(43)40-28(15-21-9-5-4-6-10-21)32(42)39-14-8-13-29(39)35(40,44)45-34/h4-7,9-12,16,18,20,23,27-29,36,44H,8,13-15,17,19H2,1-3H3,(H,37,41) |
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| InChI Key | InChIKey=HEFIYUQVAZFDEE-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as ergotamines, dihydroergotamines, and derivatives. These are organic compounds containing an ergotamine moiety, which is structurally characterized by a benzyl substituent attached to the piperazine ring of the ergopeptine backbone. |
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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 | Ergotamines, dihydroergotamines, and derivatives |
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| Alternative Parents | |
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| Substituents | - Ergotamine
- Hybrid peptide
- Alpha-dipeptide
- Lysergic acid amide
- Indoloquinoline
- Benzoquinoline
- Quinoline-3-carboxamide
- N-acyl-alpha amino acid or derivatives
- Pyrroloquinoline
- Quinoline
- Alpha-amino acid or derivatives
- 3-alkylindole
- Indole
- Indole or derivatives
- Isoindole or derivatives
- Aralkylamine
- N-alkylpiperazine
- Monocyclic benzene moiety
- 1,4-diazinane
- Benzenoid
- Oxazolidinone
- Piperazine
- Pyrrole
- Pyrrolidine
- Heteroaromatic compound
- Oxazolidine
- Tertiary carboxylic acid amide
- Carboxamide group
- Tertiary amine
- Amino acid or derivatives
- Lactam
- Tertiary aliphatic amine
- Secondary carboxylic acid amide
- Orthocarboxylic acid derivative
- Carboxylic acid derivative
- Organoheterocyclic compound
- Alkanolamine
- Oxacycle
- Azacycle
- Organooxygen compound
- Organic nitrogen compound
- Organopnictogen compound
- Carbonyl group
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Amine
- Organonitrogen compound
- 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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| LC-MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-0adi-0089000000-aeb1e8528313eebff9d2 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-05fr-0192000000-6a63208107ddccf9b39d | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0006-0013093000-1b0fea51c7fe0dedfde9 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0000039000-c69211be46cc2870d7bc | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 50V, Positive | splash10-05fr-0390000000-e1f07783820b230966fc | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0006-0013093000-608600897b7d5682d5f7 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-0adi-0089000000-9f03a24b346c4a0525f9 | 2021-09-20 | View Spectrum | | LC-MS/MS | LC-MS/MS Spectrum - 50V, Positive | splash10-05fr-0390000000-c889004b1cbb17a2939b | 2021-09-20 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0012029000-9a018cf7b722914999a0 | 2016-08-01 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0zfu-3092021000-0a198fcee08b7c28091d | 2016-08-01 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00di-6291000000-37a1ed4ec31119a247d8 | 2016-08-01 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-08fr-0029024000-98afdccc16056646ad0b | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00kr-3279061000-aebfaeae22d86e744678 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0g4i-9730000000-37e2f6daf69bab611e50 | 2016-08-03 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0000009000-d646e0db5d212a9b1f86 | 2021-10-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-0084049000-93ad6ca9490700177497 | 2021-10-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00di-0090020000-64570a453017341fe142 | 2021-10-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0000009000-21c3927cf13f38eaf54f | 2021-10-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-0066029000-1052a1acaceff9c662e9 | 2021-10-12 | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-006x-2192001000-a805021c248fab52d515 | 2021-10-12 | View Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Oral, dermal, inhalation, and parenteral (contaminated drugs). (5) |
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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. Ergometrine is also known to have a non-receptor specific oxytocic activity. (2, 3, 4) |
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| Metabolism | Not Available |
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| Toxicity Values | Not Available |
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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 | Ergocristine 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. Ergocristine is one of 3 similar peptides referred to as ergotoxine alkaloids, the other two being ergocryptine and ergocornine. Ergotoxines prepared into their hihydroergotoxine mesylates, commonly known as ergoloid mesylates, are used in the symptomatic therapy of age-related dementia. (6, 3) |
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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. (7) |
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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. (8) |
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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 | 31116 |
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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 | Ergocristine |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | Not Available |
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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 ]
- 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]
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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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