<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3821</id>
  <title>T3D3767</title>
  <common-name>Lolitrem B</common-name>
  <description>Paspalinine is a tremorgenic mycotoxin that is produced by the fungi Neotyphodium lolii and Acremonium lolii. It may be found in contaminated cereal crops such as oats, barley, millet, corn and rice. Tremorgenic mycotoxins affect central nervous system activity and have been implicated in a number of neurologic diseases of cattle collectively known as "staggers syndromes" or “ryegrass staggers”. (A2976, A3066, A3068)</description>
  <cas>81771-19-9</cas>
  <pubchem-id>3086140</pubchem-id>
  <chemical-formula>C42H55NO7</chemical-formula>
  <weight nil="true"/>
  <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>The neurological effects of Lolitrem B are a result of its ability to inhibit large conductance calcium-activated potassium channels (BK channels). Lolitrem B binds to the alpha subunit of the BK channel, inhibiting channel potassium currents. This causes tremorgenic effects either by directly affecting channels in the muscle or by acting on channels in the central nervous system. (A3066, A3067)</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>Lolitrem B is a tremorgenic mycotoxin that is produced by the fungi Neotyphodium lolii and Acremonium lolii. It may be found in contaminated cereal crops such as oats, barley, millet, corn and rice. (A2976, A3066, A3068)</use-source>
  <min-risk-level>Symptoms of "ryegrass staggers" develop in livestock when concentrations exceed 2.5 ug/g in dry matter. (A3068)</min-risk-level>
  <health-effects>Tremorgenic mycotoxins affect central nervous system activity. They cause a neurological disease of cattle known as "staggers syndrome" or “ryegrass staggers”. (A2976, A3066)</health-effects>
  <symptoms>Tremorgenic mycotoxins affect central nervous system activity, inducing neurologic symptoms including mental confusion, paralysis, tremors, seizures, and death. They cause a neurological disease of cattle known as "staggers syndrome" or “ryegrass staggers”, which is characterized by impaired motor coordination, muscle tremors, hyperexcitability, convulsions, and ataxia. Additional symptoms include increased blood pressure, heart rate and respiration rate. While the neurotoxic effects of lolitrem B have a long duration, they are also reversible. (A2976, A3066, A3067, A3068) </symptoms>
  <treatment>To control severe tremors caused by tremorgenic mycotoxins, methocarbamol should be administered. Generalized seizures may be treated with diazepam followed by methocarbamol or a barbiturate such as pentobarbital sodium. Gastric lavage should be performed and activated charcoal administered to limit further absorption of toxins. (T318)</treatment>
  <created-at type="dateTime">2010-05-20T16:06:57Z</created-at>
  <updated-at type="dateTime">2026-04-05T15:23:41Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia nil="true"/>
  <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)=CC1OC2C3OC33C(CCC4(C)C5(C)C(CC6=C5NC5=C6C6=C(C=C5)C(=O)C5C(C6)C(C)(C)OC5(C)C)CCC34O)OC2C(C)(C)O1</moldb-smiles>
  <moldb-formula>C42H55NO7</moldb-formula>
  <moldb-inchi>InChI=1S/C42H55NO7/c1-20(2)17-28-47-32-34(38(7,8)48-28)46-27-14-15-39(9)40(10)21(13-16-41(39,45)42(27)35(32)49-42)18-24-29-23-19-25-30(37(5,6)50-36(25,3)4)31(44)22(23)11-12-26(29)43-33(24)40/h11-12,17,21,25,27-28,30,32,34-35,43,45H,13-16,18-19H2,1-10H3</moldb-inchi>
  <moldb-inchikey>HGBZMCXKHKZYBF-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">685.8886</moldb-average-mass>
  <moldb-mono-mass type="decimal">685.397853119</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id nil="true"/>
  <chembl-id nil="true"/>
  <chemspider-id nil="true"/>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002734</chemdb-id>
  <dsstox-id>DTXSID40897234</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00075450</susdat-id>
  <iupac nil="true"/>
  <moldb-polar-surface-area>102.54</moldb-polar-surface-area>
  <moldb-refractivity>189.21600000000007</moldb-refractivity>
  <moldb-polarizability>79.93698313178362</moldb-polarizability>
  <moldb-rotatable-bond-count>1</moldb-rotatable-bond-count>
  <moldb-acceptor-count>7</moldb-acceptor-count>
  <moldb-donor-count>2</moldb-donor-count>
  <moldb-pka-strongest-acidic>13.145436853461753</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>-3.598610617323176</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>10</moldb-number-of-rings>
  <moldb-alogps-logp>5.75</moldb-alogps-logp>
  <moldb-alogps-logs>-6.50</moldb-alogps-logs>
  <moldb-alogps-solubility>2.18e-04 g/l</moldb-alogps-solubility>
</compound>
