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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 NumberT3D3095
Identification
Common NameHyoscyamine
ClassSmall Molecule
DescriptionHyoscyamine 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.
Compound Type
  • Amine
  • Anti-Arrhythmia Agent
  • Antispasmodic
  • Drug
  • Ester
  • Ether
  • Metabolite
  • Muscarinic Antagonist
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
Synonyms
Synonym
(-)-Atropine
(-)-Hyoscyamine
(leo)-atropine
(leo)-hyoscyamine
(S)-(-)-Hyoscyamine
(S)-(leo)-hyoscyamine
(S)-(−)-hyoscyamine
(S)-atropine
(S)atropine
(−)-atropine
(−)-hyoscyamine
Acupaz
Anapaz
Anaspaz
Atropen
Boots Travel Calm
Buwecon
Cystospaz
Cytospaz
Daturin
Daturine
Donnamar
Duboisine
Egazil
Hyocyamine
Hyoscyamin
Hyoscyaminum
L-Atropine
L-Hyopscyamine
L-Hyoscamine
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 Number101-31-5
IUPAC Name(1R,3R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2S)-3-hydroxy-2-phenylpropanoate
Traditional Namelevbid
SMILES[H][C@](CO)(C(=O)O[C@]1([H])C[C@]2([H])CC[C@]([H])(C1)N2C)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/t13-,14+,15+,16-/m1/s1
InChI KeyInChIKey=RKUNBYITZUJHSG-FXUDXRNXSA-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
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
Salivary secretionNot Availablemap04970
Gastric acid secretionNot Availablemap04971
Insulin secretionNot Availablemap04911
Cholinergic synapseNot Availablemap04725
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point108.5°C
Boiling PointNot Available
Solubility3560 mg/L (at 20°C)
LogP1.8
Predicted Properties
PropertyValueSource
Water Solubility2.52 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity80.82 m3·mol-1ChemAxon
Polarizability31.74 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-00di-5900000000-f705f96b0219dcd47d66View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS)splash10-0006-4900000000-d0c3228da9df55297f7bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-006x-6951100000-43127e046c478d2643e1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-006x-6951100000-43127e046c478d2643e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0790000000-b3809a4d9f3d53472626View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1920000000-5cf6a284aa0360bfa6f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0g02-2900000000-03a359b67b71a8d41b5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0490000000-42268e6db552a2d85a66View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05g3-1960000000-db1243e11ae5ea609f09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00bc-5900000000-3453e9ae42b1ccba243cView in MoNA
MSMass Spectrum (Electron Ionization)splash10-00di-9810000000-bdd60b3a23f97899d426View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Toxicity Profile
Route of ExposureOral (ingestion) (3) ; dermal (3). Absorbed totally and completely by sublingual administration as well as oral administration.
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) 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.
MetabolismHepatic Half Life: 2-3.5 hours
Toxicity Values LD50=mg/kg (orally in rat)
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 IDHMDB14568
PubChem Compound ID64692
ChEMBL IDCHEMBL1331216
ChemSpider ID10246417
KEGG IDC02046
UniProt IDNot Available
OMIM ID
ChEBI ID17486
BioCyc IDCPD-2202
CTD IDNot Available
Stitch IDL-Hyoscyamine
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkHyoscyamine
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.

MSDSLink
General References
  1. Wikipedia. Hyoscyamine. Last Updated 10 June 2009. [Link]
  2. Drugs.com [Link]
  3. Wikipedia. Phytotoxin. Last Updated 7 August 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Wikipedia. Hyoscyamine. Last Updated 10 June 2009. [Link]
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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. 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. 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. 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]