<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">3137</id>
  <title>T3D3095</title>
  <common-name>Hyoscyamine</common-name>
  <description>Hyoscyamine is a chemical compound, a tropane alkaloid it is the levo-isomer to atropine. It is a secondary metabolite of some plants, particularly henbane (Hyoscamus niger.)Hyoscyamine is used to provide symptomatic relief to various gastrointestinal disorders including spasms, peptic ulcers, irritable bowel syndrome, pancreatitis, colic and cystitis. It has also been used to relieve some heart problems, control some of the symptoms of Parkinson's disease, as well as for control of respiratory secretions in end of life care.</description>
  <cas>101-31-5</cas>
  <pubchem-id>64692</pubchem-id>
  <chemical-formula>C17H23NO3</chemical-formula>
  <weight>289.167790</weight>
  <appearance>White powder.</appearance>
  <melting-point>108.5°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>3560 mg/L (at 20°C)</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral (ingestion) (L1817) ; dermal (L1817). Absorbed totally and completely by sublingual administration as well as oral administration.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Hyoscyamine is an anticholinergic, specifically an antimuscarinic, and works by blocking the action of acetylcholine at parasympathetic sites in smooth muscle, secretory glands, and the central nervous system. (L1255)Hyoscyamine competes favorably with acetylcholine for binding at muscarinic receptors in the salivary, bronchial, and sweat glands as well as in the eye, heart, and gastrointestinal tract. The actions of hyoscyamine result in a reduction in salivary, bronchial, gastric and sweat gland secretions, mydriasis, cycloplegia, change in heart rate, contraction of the bladder detrusor muscle and of the gastrointestinal smooth muscle, and decreased gastrointestinal motility.</mechanism-of-toxicity>
  <metabolism>HepaticHalf Life: 2-3.5 hours</metabolism>
  <toxicity> LD&lt;sub&gt;50&lt;/sub&gt;=mg/kg (orally in rat)</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Hyoscyamine is a plant toxin found in certain plants of the Solanaceae family, including henbane (Hyoscyamus niger), mandrake (Mandragora officinarum), jimsonweed (Datura stramonium), and deadly nightshade (Atropa belladonna). It is used as a drug to provide symptomatic relief to various gastrointestinal disorders including spasms, peptic ulcers, irritable bowel syndrome, pancreatitis, colic and cystitis. It has also been used to relieve some heart problems, control some of the symptoms of Parkinson's disease, as well as for control of respiratory secretions in palliative care.(L1255)</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Hyoscyamine affects the central nervous system. (L1255)</health-effects>
  <symptoms>Side effects of hyoscyamine include dry mouth and throat, eye pain, blurred vision, restlessness, dizziness, arrythmia, flushing, and faintness. An overdose will cause headache, nausea, vomiting, and central nervous system symptoms including disorientation, hallucinations, euphoria, sexual arousal, short-term memory loss, and possible coma in extreme cases. (L1255)</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2009-07-23T18:26:14Z</created-at>
  <updated-at type="dateTime">2026-05-14T16:38:21Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Hyoscyamine</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C02046</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>17486</chebi-id>
  <biocyc-id>CPD-2202</biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>L-Hyoscyamine</stitch-id>
  <drugbank-id>DB00424</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]2CC[C@@H]1C[C@@H](C2)OC(=O)[C@H](CO)C1=CC=CC=C1</moldb-smiles>
  <moldb-formula>C17H23NO3</moldb-formula>
  <moldb-inchi>InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15+,16-/m1/s1</moldb-inchi>
  <moldb-inchikey>RKUNBYITZUJHSG-FXUDXRNXSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">289.3694</moldb-average-mass>
  <moldb-mono-mass type="decimal">289.167793607</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>1.8</logp>
  <hmdb-id>HMDB14568</hmdb-id>
  <chembl-id>CHEMBL1331216</chembl-id>
  <chemspider-id>10246417</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;Jeffrey Kiel, H. Thomas, Emily Ware, Brady Ware, &amp;#8220;Phenolic acid complexes of hyoscyamine and process for preparing the same.&amp;#8221; U.S. Patent US20060128637, issued June 15, 2006.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002430</chemdb-id>
  <dsstox-id>DTXSID80889335</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00066992</susdat-id>
  <iupac>(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2S)-3-hydroxy-2-phenylpropanoate</iupac>
  <moldb-polar-surface-area>49.77</moldb-polar-surface-area>
  <moldb-refractivity>80.81640000000002</moldb-refractivity>
  <moldb-polarizability>31.741089874876113</moldb-polarizability>
  <moldb-rotatable-bond-count>5</moldb-rotatable-bond-count>
  <moldb-acceptor-count>3</moldb-acceptor-count>
  <moldb-donor-count>1</moldb-donor-count>
  <moldb-pka-strongest-acidic>15.145740617562414</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>9.385561870758496</moldb-pka-strongest-basic>
  <moldb-physiological-charge>1</moldb-physiological-charge>
  <moldb-number-of-rings>3</moldb-number-of-rings>
  <moldb-alogps-logp>2.19</moldb-alogps-logp>
  <moldb-alogps-logs>-2.06</moldb-alogps-logs>
  <moldb-alogps-solubility>2.52e+00 g/l</moldb-alogps-solubility>
</compound>
