D-Hyoscyamine (CHEM002431)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (6)XML
Record Information
Version1.0
Creation Date2009-07-23 18:26:14 UTC
Update Date2016-11-09 01:08:46 UTC
Accession NumberCHEM002431
Identification
Common NameD-Hyoscyamine
ClassSmall Molecule
DescriptionHyoscyamine 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.(1)
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amine
  • Anti-Arrhythmia Agent
  • Antispasmodic
  • Drug
  • Ester
  • Ether
  • Muscarinic Antagonist
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+-)-AtropineChEBI
(+-)-HyoscyamineChEBI
(+,-)-Tropyl tropateChEBI
(3-endo)-8-Methyl-8-azabicyclo[3.2.1]oct-3-yl tropateChEBI
8-Methyl-8-azabicyclo[3.2.1]oct-3-yl 3-hydroxy-2-phenylpropanoateChEBI
8-Methyl-8-azabicyclo[3.2.1]oct-3-yl tropateChEBI
[(1S,5R)-8-Methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-hydroxy-2-phenyl-propanoateChEBI
AtropinChEBI
AtropinaChEBI
DL-HyoscyamineChEBI
DL-TropyltropateChEBI
Tropine tropateChEBI
AtropenKegg
(+,-)-Tropyl tropic acidGenerator
(3-endo)-8-Methyl-8-azabicyclo[3.2.1]oct-3-yl tropic acidGenerator
8-Methyl-8-azabicyclo[3.2.1]oct-3-yl 3-hydroxy-2-phenylpropanoic acidGenerator
8-Methyl-8-azabicyclo[3.2.1]oct-3-yl tropic acidGenerator
[(1S,5R)-8-Methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-hydroxy-2-phenyl-propanoic acidGenerator
DL-Tropyltropic acidGenerator
Tropine tropic acidGenerator
Atropine sulfateHMDB
DL-Tropyl tropateHMDB
Chemical FormulaC17H23NO3
Average Molecular Mass289.369 g/mol
Monoisotopic Mass289.168 g/mol
CAS Registry Number13269-35-7
IUPAC Name(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate
Traditional Name(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate
SMILESCN1C2CCC1CC(C2)OC(=O)C(CO)C1=CC=CC=C1
InChI IdentifierInChI=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
InChI KeyRKUNBYITZUJHSG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassTropane alkaloids
Sub ClassNot Available
Direct ParentTropane alkaloids
Alternative Parents
Substituents
  • Tropane alkaloid
  • Beta-hydroxy acid
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Piperidine
  • Benzenoid
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organic nitrogen compound
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.52 g/LALOGPS
logP2.19ALOGPS
logP1.57ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)15.15ChemAxon
pKa (Strongest Basic)9.39ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.77 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity80.82 m³·mol⁻¹ChemAxon
Polarizability31.28 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-5900000000-f705f96b0219dcd47d66Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-4900000000-d0c3228da9df55297f7bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-006x-6951100000-dad9042cce0338579e31Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-0090000000-b8bc13dbb3c507a0f6b6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-0190000000-c8603eb138fb8f0e3404Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00dl-3940000000-da1a38da6babdc138c49Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-006x-9700000000-2f9f7ce546a61df93bfaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-9300000000-6a976c404c7b299bbdd6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-9200000000-0eb0ff987d891c85a047Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0090000000-59d025c22f64675dc295Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0090000000-661bc87f4d92ae6353d7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00dl-1960000000-dafd68e61cc5909f5decSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00dl-7900000000-48d355c9eef2af0979ccSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9300000000-659231292b6eba371158Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-00di-2900000000-3d5f34ceb343969b3c91Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF , positivesplash10-00fr-0900000000-a216bda74712aba9b341Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-006x-6951100000-dad9042cce0338579e31Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0790000000-b3809a4d9f3d53472626Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1920000000-5cf6a284aa0360bfa6f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0g02-2900000000-03a359b67b71a8d41b5aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0490000000-42268e6db552a2d85a66Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05g3-1960000000-db1243e11ae5ea609f09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00bc-5900000000-3453e9ae42b1ccba243cSpectrum
Toxicity Profile
Route of ExposureOral (ingestion) (2) ; dermal (2)
Mechanism of ToxicityHyoscyamine 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. (1)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesHyoscyamine 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.(1)
Minimum Risk LevelNot Available
Health EffectsHyoscyamine affects the central nervous system. (1)
SymptomsSide 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. (1)
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00572
HMDB IDHMDB0014712
FooDB IDFDB004090
Phenol Explorer IDNot Available
KNApSAcK IDC00002277
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAtropine
Chemspider ID10194105
ChEBI ID16684
PubChem Compound IDNot Available
Kegg Compound IDC01479
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Jeffrey Kiel, H. Thomas, Emily Ware, Brady Ware, “Phenolic acid complexes of hyoscyamine and process for preparing the same.” U.S. Patent US20060128637, issued June 15, 2006.

MSDSNot Available
General References
1. Thomson R: Side effects and placebo amplification. Br J Psychiatry. 1982 Jan;140:64-8.
2. Hervada AR, Feit E, Sagraves R: Drugs in breast milk. Perinat Care. 1978 Sep;2(8):19-25.
3. Brodie MS, Proudfit HK: Hypoalgesia induced by the local injection of carbachol into the nucleus raphe magnus. Brain Res. 1984 Jan 23;291(2):337-42.
4. Bryant KR, Rothwell NJ, Stock MJ, Wyllie MG: Parasympathethic effects on diet-induced thermogenesis. Eur J Pharmacol. 1983 Nov 25;95(3-4):291-4.
5. Yamazaki Z, Tagaya I: Antiviral effects of atropine and caffeine. J Gen Virol. 1980 Oct;50(2):429-31.
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=15374592
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=18369575