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<compound>
  <id type="integer">3744</id>
  <title>T3D3691</title>
  <common-name>Ergovaline</common-name>
  <description>Ergovaline is a solid compound with the chemical formula C29H35N5O5. Ergovaline belongs to the lysergic acids and derivatives, a subclass of ergoline and derivatives within the organic compounds. With an average molecular weight of 533.62 g/mol, Ergovaline is a heavy molecule. This exogenous substance has been found in or released from 13 recorded sources, including electrical and electronic equipment such as cell phones, capacitors, wires and cables, batteries, and printed circuit boards; textiles, leather and furnishings, including synthetic textiles, carpets and rugs; food packaging; medical devices; and lubricants used in energy, oil, gas, industrial manufacturing, and chemical processing. Recorded exposure routes include inhalation, oral, and touch.

The compound interacts with seven recorded protein targets. Ergovaline acts as an agonist at the D(2) dopamine receptor (DRD2), inhibiting cyclic AMP production and creating second messenger responses similar to those of dopamine. It also acts as an agonist at vascular 5-hydroxytryptamine receptors 2A (HTR2A), 1B (HTR1B), and 1D (HTR1D), which causes the constriction of blood vessels. Additionally, Ergovaline acts as a partial agonist at alpha-1 adrenoreceptors, specifically the Alpha-1A adrenergic receptor (ADRA1A), Alpha-1B adrenergic receptor (ADRA1B), and Alpha-1D adrenergic receptor (ADRA1D), thereby inhibiting the contractile response to norepinephrine.</description>
  <cas>2873-38-3</cas>
  <pubchem-id>104843</pubchem-id>
  <chemical-formula>C29H35N5O5</chemical-formula>
  <weight>533.6</weight>
  <appearance>White powder.</appearance>
  <melting-point nil="true"/>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility nil="true"/>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)</route-of-exposure>
  <target nil="true"/>
  <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. (A2914, A2915, A2916)</mechanism-of-toxicity>
  <metabolism nil="true"/>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Ergovaline is an ergopeptine and 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. (L1918)</use-source>
  <min-risk-level nil="true"/>
  <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. (A2913)</health-effects>
  <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. (L1920)</symptoms>
  <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. (L1921)</treatment>
  <created-at type="dateTime">2010-04-23T21:10:16Z</created-at>
  <updated-at type="dateTime">2026-08-22T09:07:47Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>http://en.wikipedia.org/wiki/Ergovaline</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id nil="true"/>
  <omim-id nil="true"/>
  <chebi-id nil="true"/>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id nil="true"/>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CC(C)C1N2C(=O)C(C)(NC(=O)C3CN(C)C4CC5=CNC6=CC=CC(=C56)C4=C3)OC2(O)C2CCCN2C1=O</moldb-smiles>
  <moldb-formula>C29H35N5O5</moldb-formula>
  <moldb-inchi>InChI=1S/C29H35N5O5/c1-15(2)24-26(36)33-10-6-9-22(33)29(38)34(24)27(37)28(3,39-29)31-25(35)17-11-19-18-7-5-8-20-23(18)16(13-30-20)12-21(19)32(4)14-17/h5,7-8,11,13,15,17,21-22,24,30,38H,6,9-10,12,14H2,1-4H3,(H,31,35)</moldb-inchi>
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  <moldb-average-mass type="decimal">533.6187</moldb-average-mass>
  <moldb-mono-mass type="decimal">533.263819255</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>1.4</logp>
  <hmdb-id nil="true"/>
  <chembl-id nil="true"/>
  <chemspider-id>94635</chemspider-id>
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  <biodb-id nil="true"/>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002660</chemdb-id>
  <dsstox-id>DTXSID10893243</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00094895</susdat-id>
  <iupac>(6aR,9R)-N-[(1S,2S,4R,7S)-2-hydroxy-4-methyl-5,8-dioxo-7-propan-2-yl-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide</iupac>
  <moldb-polar-surface-area>118.21000000000002</moldb-polar-surface-area>
  <moldb-refractivity>144.5444</moldb-refractivity>
  <moldb-polarizability>56.35974126088264</moldb-polarizability>
  <moldb-rotatable-bond-count>3</moldb-rotatable-bond-count>
  <moldb-acceptor-count>6</moldb-acceptor-count>
  <moldb-donor-count>3</moldb-donor-count>
  <moldb-pka-strongest-acidic>9.695485603868692</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>7.7804845304204955</moldb-pka-strongest-basic>
  <moldb-physiological-charge>1</moldb-physiological-charge>
  <moldb-number-of-rings>7</moldb-number-of-rings>
  <moldb-alogps-logp>2.44</moldb-alogps-logp>
  <moldb-alogps-logs>-3.10</moldb-alogps-logs>
  <moldb-alogps-solubility>4.26e-01 g/l</moldb-alogps-solubility>
  <kingdom>Organic compounds</kingdom>
  <superklass>Alkaloids and derivatives</superklass>
  <klass>Ergoline and derivatives</klass>
  <subklass>Lysergic acids and derivatives</subklass>
  <paper-count type="integer">219</paper-count>
  <sync-id>CED0011785</sync-id>
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  <structure-indexed-at type="dateTime">2026-09-19T04:00:52Z</structure-indexed-at>
</compound>
