<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2919</id>
  <title>T3D2877</title>
  <common-name>Scopolamine</common-name>
  <description>Scopolamine, also known as hyoscine, is a tropane alkaloid drug obtained from plants of the family Solanaceae (nightshades), such as henbane or jimson weed (Datura species). It is part of the secondary metabolites of plants. Scopolamine is used criminally as a date rape drug and as an aid to robbery, the most common act being the clandestine drugging of a victim's drink. It is preferred because it induces retrograde amnesia, or an inability to recall events prior to its administration. Victims of this crime are often admitted to a hospital in police custody, under the assumption that the patient is experiencing a psychotic episode. A telltale sign is a fever accompanied by a lack of sweat. An alkaloid from Solanaceae, especially Datura metel L. and Scopola carniolica. Scopolamine and its quaternary derivatives act as antimuscarinics like atropine, but may have more central nervous system effects. Among the many uses are as an anesthetic premedication, in urinary incontinence, in motion sickness, as an antispasmodic, and as a mydriatic and cycloplegic.</description>
  <cas>51-34-3</cas>
  <pubchem-id>5184</pubchem-id>
  <chemical-formula>C17H21NO4</chemical-formula>
  <weight>303.147060</weight>
  <appearance>White powder.</appearance>
  <melting-point>59°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>1E+005 mg/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Parental (intravenous, intramuscular, and transdermal); oral</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Scopolamine acts by interfering with the transmission of nerve impulses by acetylcholine in the parasympathetic nervous system (specifically the vomiting center).</mechanism-of-toxicity>
  <metabolism>Route of Elimination: Less than 10% of the total dose is excreted in the urine as parent and metabolites over 108 hours.Half Life: 4.5 hours</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>For the treatment of excessive salivation, colicky abdominal pain, bradycardia, sialorrhoea, diverticulitis, irritable bowel syndrome and motion sickness.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms></symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2009-07-21T20:27:33Z</created-at>
  <updated-at type="dateTime">2026-05-14T16:47:46Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Scopolamine</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C01851</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>16794</chebi-id>
  <biocyc-id>SCOPOLAMINE</biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Scopolamine</stitch-id>
  <drugbank-id>DB00747</drugbank-id>
  <pdb-id></pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CN1[C@H]2C[C@@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)[C@H](CO)C1=CC=CC=C1</moldb-smiles>
  <moldb-formula>C17H21NO4</moldb-formula>
  <moldb-inchi>InChI=1S/C17H21NO4/c1-18-13-7-11(8-14(18)16-15(13)22-16)21-17(20)12(9-19)10-5-3-2-4-6-10/h2-6,11-16,19H,7-9H2,1H3/t11-,12-,13-,14+,15-,16+/m1/s1</moldb-inchi>
  <moldb-inchikey>STECJAGHUSJQJN-FWXGHANASA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">303.3529</moldb-average-mass>
  <moldb-mono-mass type="decimal">303.147058165</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>0.98</logp>
  <hmdb-id>HMDB03573</hmdb-id>
  <chembl-id>CHEMBL1201069</chembl-id>
  <chemspider-id>10194106</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>&lt;p&gt;Yang Guodong, &amp;#8220;Preparation and application of scopolamine and chlorpromazine as a drug-withdrawal agent.&amp;#8221; U.S. Patent US5543407, issued February, 1993.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002264</chemdb-id>
  <dsstox-id>DTXSID6023573</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00001110</susdat-id>
  <iupac>(1R,2R,4S,5S,7S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate</iupac>
  <moldb-polar-surface-area>62.3</moldb-polar-surface-area>
  <moldb-refractivity>79.72130000000003</moldb-refractivity>
  <moldb-polarizability>31.24346801979366</moldb-polarizability>
  <moldb-rotatable-bond-count>5</moldb-rotatable-bond-count>
  <moldb-acceptor-count>4</moldb-acceptor-count>
  <moldb-donor-count>1</moldb-donor-count>
  <moldb-pka-strongest-acidic>15.145739865848086</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>6.953523808607151</moldb-pka-strongest-basic>
  <moldb-physiological-charge>1</moldb-physiological-charge>
  <moldb-number-of-rings>4</moldb-number-of-rings>
  <moldb-alogps-logp>1.40</moldb-alogps-logp>
  <moldb-alogps-logs>-1.66</moldb-alogps-logs>
  <moldb-alogps-solubility>6.61e+00 g/l</moldb-alogps-solubility>
</compound>
