<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2492</id>
  <title>T3D2452</title>
  <common-name>(2S,4R,5S)-Muscarine</common-name>
  <description>(2S,4R,5S)-Muscarine is an exogenous organic compound with the formula C9H20NO2 and an average molecular weight of 174.26 g/mol. It exists as a solid at room temperature. (2S,4R,5S)-Muscarine belongs to the carbohydrates and carbohydrate conjugates, a subclass of organooxygen compounds within the organic compounds.

The compound acts as a competitive inhibitor that mimics the action of the neurotransmitter acetylcholine at acetylcholine receptors. It has eight recorded protein targets, including the acetylcholine receptor subunits alpha (CHRNA1), beta (CHRNB1), delta (CHRND), and epsilon (CHRNE). Additionally, it targets the muscarinic acetylcholine receptors M1 (CHRM1), M2 (CHRM2), and M4 (CHRM4).</description>
  <cas>300-54-9</cas>
  <pubchem-id>5079496</pubchem-id>
  <chemical-formula>C9H20NO2</chemical-formula>
  <weight></weight>
  <appearance>White powder.</appearance>
  <melting-point></melting-point>
  <boiling-point></boiling-point>
  <density></density>
  <solubility></solubility>
  <specific-gravity></specific-gravity>
  <flash-point></flash-point>
  <vapour-pressure></vapour-pressure>
  <route-of-exposure>Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Muscarine is a competitive inhibitor. It mimics the action of the neurotransmitter acetylcholine at acetylcholine receptors. (L1011)</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>Muscarine is only a trace compound in the fly agaric Amanita muscaria; the pharmacologically more relevant compound from this mushroom is muscimol.

Mushrooms in the genera Entoloma and Mycena have also been found to contain levels of muscarine which can be dangerous if ingested. Muscarine has been found in harmless trace amounts in Boletus, Hygrocybe, Lactarius and Russula. (L1011)</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Intoxication generally subsides within 2 hours. Death is rare, but may result from cardiac or respiratory failure in severe cases. (L1011)</health-effects>
  <symptoms>Muscarine poisoning is characterized by increased salivation, sweating (perspiration), and tearflow (lacrimation) within 15 to 30 minutes after ingestion of the mushroom. With large doses, these symptoms may be followed by abdominal pain, severe nausea, diarrhea, blurred vision, and labored breathing. (L1011)</symptoms>
  <treatment>The specific antidote is atropine. (L1011)</treatment>
  <created-at type="dateTime">2009-07-03T20:53:35Z</created-at>
  <updated-at type="dateTime">2026-04-03T21:35:00Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>http://en.wikipedia.org/wiki/Muscarine</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C07473</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>522933</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id>D009116</ctd-id>
  <stitch-id>Muscarine</stitch-id>
  <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>[H][C@@]1(C)O[C@]([H])(C[N+](C)(C)C)C[C@@]1([H])O</moldb-smiles>
  <moldb-formula>C9H20NO2</moldb-formula>
  <moldb-inchi>InChI=1S/C9H20NO2/c1-7-9(11)5-8(12-7)6-10(2,3)4/h7-9,11H,5-6H2,1-4H3/q+1/t7-,8-,9+/m0/s1</moldb-inchi>
  <moldb-inchikey>UQOFGTXDASPNLL-XHNCKOQMSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">174.2601</moldb-average-mass>
  <moldb-mono-mass type="decimal">174.148855309</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id>HMDB29936</hmdb-id>
  <chembl-id nil="true"/>
  <chemspider-id>4255959</chemspider-id>
  <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 nil="true"/>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002041</chemdb-id>
  <dsstox-id>DTXSID50184081</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00028831</susdat-id>
  <iupac nil="true"/>
  <moldb-polar-surface-area>29.46</moldb-polar-surface-area>
  <moldb-refractivity>59.893100000000004</moldb-refractivity>
  <moldb-polarizability>20.10146678640744</moldb-polarizability>
  <moldb-rotatable-bond-count>2</moldb-rotatable-bond-count>
  <moldb-acceptor-count>2</moldb-acceptor-count>
  <moldb-donor-count>1</moldb-donor-count>
  <moldb-pka-strongest-acidic>14.11178387341359</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>-3.1873057337688957</moldb-pka-strongest-basic>
  <moldb-physiological-charge>1</moldb-physiological-charge>
  <moldb-number-of-rings>1</moldb-number-of-rings>
  <moldb-alogps-logp>-2.98</moldb-alogps-logp>
  <moldb-alogps-logs>-2.51</moldb-alogps-logs>
  <moldb-alogps-solubility>6.41e-01 g/l</moldb-alogps-solubility>
  <kingdom>Organic compounds</kingdom>
  <superklass>Organic oxygen compounds</superklass>
  <klass>Organooxygen compounds</klass>
  <subklass>Carbohydrates and carbohydrate conjugates</subklass>
  <paper-count type="integer">0</paper-count>
  <sync-id>CED0048937</sync-id>
  <structure-inchikey>UQOFGTXDASPNLL-XHNCKOQMSA-N</structure-inchikey>
  <structure-fingerprint>2000000800000000000800000000000000000000000000000000000000000000001000000000010000000000002000000000000000000000000000000000000000000000000000008000000800000000800000020000000000000000000010000000000400000000000200000020000000000000000000000100000000040000000000000000000000000000000000000000000000000400000000800040000000000000000000100000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000000040000000000000000000010200000000</structure-fingerprint>
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  <structure-indexed-at type="dateTime">2026-09-19T04:00:28Z</structure-indexed-at>
</compound>
