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Record Information
Version2.0
Creation Date2009-07-23 18:26:14 UTC
Update Date2014-12-24 20:25:58 UTC
Accession NumberT3D3096
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)
Compound Type
  • Amine
  • Anti-Arrhythmia Agent
  • Antispasmodic
  • Drug
  • Ester
  • Ether
  • Muscarinic Antagonist
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
Synonyms
Synonym
(-)-Atropine
(-)-Hyoscyamine
(S)-(-)-Hyoscyamine
(S)-(−)-hyoscyamine
(S)-atropine
(−)-atropine
(−)-hyoscyamine
Acupaz
Anapaz
Anaspaz
Atropen
Boots Travel Calm
Buwecon
Cystospaz
Cytospaz
Daturin
Daturine
Donnamar
Duboisine
Egazil
Hyoscyamin
Hyoscyamine
Hyoscyaminum
L-Hyoscyamine
L-Tropine Tropate
Levbid
Levsin
Levsinex
NuLev
Symax
Tropine, (-)-tropate
Tropine-L-tropate
[3(S)-Endo]-alpha-(hydroxymethyl)benzeneacetic acid 8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester
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=1/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 KeyInChIKey=RKUNBYITZUJHSG-UHFFFAOYNA-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
LogPNot 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-5900000000-f705f96b0219dcd47d66JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-4900000000-d0c3228da9df55297f7bJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-006x-6951100000-dad9042cce0338579e31JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-0090000000-b8bc13dbb3c507a0f6b6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-0190000000-c8603eb138fb8f0e3404JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00dl-3940000000-da1a38da6babdc138c49JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-006x-9700000000-2f9f7ce546a61df93bfaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-9300000000-6a976c404c7b299bbdd6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-9200000000-0eb0ff987d891c85a047JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0090000000-59d025c22f64675dc295JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-0090000000-661bc87f4d92ae6353d7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00dl-1960000000-dafd68e61cc5909f5decJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00dl-7900000000-48d355c9eef2af0979ccJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9300000000-659231292b6eba371158JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-00di-2900000000-3d5f34ceb343969b3c91JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF , positivesplash10-00fr-0900000000-a216bda74712aba9b341JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-006x-6951100000-dad9042cce0338579e31JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0790000000-b3809a4d9f3d53472626JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1920000000-5cf6a284aa0360bfa6f5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0g02-2900000000-03a359b67b71a8d41b5aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0490000000-42268e6db552a2d85a66JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05g3-1960000000-db1243e11ae5ea609f09JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00bc-5900000000-3453e9ae42b1ccba243cJSpectraViewer
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
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00424
HMDB IDNot Available
PubChem Compound ID637577
ChEMBL IDNot Available
ChemSpider IDNot Available
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI ID48882
BioCyc IDNot Available
CTD IDNot Available
Stitch IDD-Hyoscyamine
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot 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. Wikipedia. Hyoscyamine. Last Updated 10 June 2009. [Link]
  2. Wikipedia. Phytotoxin. Last Updated 7 August 2009. [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated GenesNot Available

Targets

General Function:
G-protein coupled acetylcholine receptor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition. Signaling promotes phospholipase C activity, leading to the release of inositol trisphosphate (IP3); this then triggers calcium ion release into the cytosol.
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular Weight:
51714.605 Da
References
  1. Nelson CP, Gupta P, Napier CM, Nahorski SR, Challiss RA: Functional selectivity of muscarinic receptor antagonists for inhibition of M3-mediated phosphoinositide responses in guinea pig urinary bladder and submandibular salivary gland. J Pharmacol Exp Ther. 2004 Sep;310(3):1255-65. Epub 2004 May 12. [15140916 ]
  2. Wikipedia. Hyoscyamine. Last Updated 10 June 2009. [Link]
General Function:
Receptor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM3
Uniprot ID:
P20309
Molecular Weight:
66127.445 Da
References
  1. Nelson CP, Gupta P, Napier CM, Nahorski SR, Challiss RA: Functional selectivity of muscarinic receptor antagonists for inhibition of M3-mediated phosphoinositide responses in guinea pig urinary bladder and submandibular salivary gland. J Pharmacol Exp Ther. 2004 Sep;310(3):1255-65. Epub 2004 May 12. [15140916 ]
  2. Wikipedia. Hyoscyamine. Last Updated 10 June 2009. [Link]
General Function:
Guanyl-nucleotide exchange factor activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is inhibition of adenylate cyclase.
Gene Name:
CHRM4
Uniprot ID:
P08173
Molecular Weight:
53048.65 Da
References
  1. Lanzafame AA, Sexton PM, Christopoulos A: Interaction studies of multiple binding sites on m4 muscarinic acetylcholine receptors. Mol Pharmacol. 2006 Aug;70(2):736-46. Epub 2006 May 18. [16709648 ]
  2. Wikipedia. Hyoscyamine. Last Updated 10 June 2009. [Link]
General Function:
Transmitter-gated ion channel activity
Specific Function:
The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing).
Gene Name:
GLRA1
Uniprot ID:
P23415
Molecular Weight:
52623.35 Da
References
  1. Jensen AA, Kristiansen U: Functional characterisation of the human alpha1 glycine receptor in a fluorescence-based membrane potential assay. Biochem Pharmacol. 2004 May 1;67(9):1789-99. [15081878 ]
General Function:
Phosphatidylinositol phospholipase c activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM1
Uniprot ID:
P11229
Molecular Weight:
51420.375 Da
References
  1. Wikipedia. Hyoscyamine. Last Updated 10 June 2009. [Link]
General Function:
Phosphatidylinositol phospholipase c activity
Specific Function:
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover.
Gene Name:
CHRM5
Uniprot ID:
P08912
Molecular Weight:
60073.205 Da
References
  1. Wikipedia. Hyoscyamine. Last Updated 10 June 2009. [Link]