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Showing Compound Scopolamine (FDB023199)

Record Information
Version1.0
Creation date2011-09-21 00:26:10 UTC
Update date2015-10-09 22:32:33 UTC
Primary IDFDB023199
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameScopolamine
DescriptionScopolamine, 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. [HMDB]
CAS Number51-34-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Boro scopolHMDB
BoroScopolHMDB
ScoburenHMDB
Winzer brand OF scopolamine borateHMDB
Bull brand OF scopolamine hydrobromideHMDB
Hamilton brand OF scopolamine hydrobromideHMDB
Hope brand OF scopolamineHMDB
Hydrobromide, scopolamineHMDB
HyoscineHMDB
Novartis brand OF scopolamineHMDB
Novartis consumer health brand OF scopolamineHMDB
Scopolamine cooperHMDB
Cooper brand OF scopolamine hydrobromideHMDB
Inibisa brand OF scopolamine hydrobromideHMDB
KwellsHMDB
Renaudin brand OF scopolamine hydrobromideHMDB
Scopoderm TTSHMDB
Scopolamine hydrobromideHMDB
Travacalm hoHMDB
VorigenoHMDB
Alcon brand OF scopolamine hydrobromideHMDB
Boro-scopolHMDB
Isopto hyoscineHMDB
Roche brand OF scopolamine hydrobromideHMDB
ScopaceHMDB
Transderm scopHMDB
Transderm VHMDB
Transderm-VHMDB
[(1S,2S,4R,5S)-9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]nonan-7-yl] (2S)-3-hydroxy-2-phenylpropanoic acidGenerator
(-)-Hyoscinehmdb
(-)-Hyoscine hydrobromidehmdb
(-)-ScopolamineChEBI
(-)-Scopolamine bromidehmdb
(-)-Scopolamine hydrobromidehmdb
(+)-Hyoscinehmdb
(+)-Scopolaminehmdb
(1S,3S,5R,6R,7S)-6,7-Epoxytropan-3-yl (2S)-3-hydroxy-2-phenylpropanoateChEBI
(1S,3S,5R,6R,7S)-6,7-Epoxytropan-3-yl (2S)-3-hydroxy-2-phenylpropanoic acidGenerator
6-b,7-b-Epoxy-3-a-tropanyl S-(-)-tropateGenerator
6-b,7-b-Epoxy-3-a-tropanyl S-(-)-tropic acidGenerator
6-beta,7-beta-Epoxy-3-alpha-tropanyl S-(-)-tropateChEBI
6-beta,7-beta-Epoxy-3-alpha-tropanyl S-(-)-tropic acidGenerator
6-β,7-β-epoxy-3-α-tropanyl S-(-)-tropateGenerator
6-β,7-β-epoxy-3-α-tropanyl S-(-)-tropic acidGenerator
6,7-Epoxytropine Tropatehmdb
6,7-Epoxytropine tropic acidGenerator
a-(Hydroxymethyl)benzeneacetate 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl esterGenerator
a-(Hydroxymethyl)benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl esterGenerator
alpha-(Hydroxymethyl)benzeneacetate 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl esterGenerator
alpha-(Hydroxymethyl)benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl esterChEBI
Atrochinhmdb
Atroquinhmdb
Beldavrinhmdb
Buscopanhmdb
Epoxytropine tropatehmdb
Euscopolhmdb
Hydroscine hydrobromidehmdb
Hyosceinehmdb
Hyoscine bromidehmdb
Hyoscine hydrobromidehmdb
Hyoscyine hydrobromidehmdb
Hyosolhmdb
Hyscohmdb
Isopto Hyoscinehmdb
Isoscopilhmdb
L-Hyoscine hydrobromidehmdb
l-Scopolamine-hydrobromidehmdb
Methscopolamine Bromidehmdb
Oscinehmdb
Paminehmdb
S-(-)-Tropatehmdb
Scophmdb
Scopaminhmdb
Scopine (-)-tropateChEBI
Scopine (-)-tropic acidGenerator
Scopine tropatehmdb
Scopolamine bromidehmdb
Scopolaminium bromidehmdb
Scopolammonium bromidehmdb
SEEhmdb
Tranaxinehmdb
Transderm-scopChEBI
α-(hydroxymethyl)benzeneacetate 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl esterGenerator
α-(hydroxymethyl)benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl esterGenerator
Predicted Properties
PropertyValueSource
Water Solubility6.61 g/LALOGPS
logP1.4ALOGPS
logP0.89ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)15.15ChemAxon
pKa (Strongest Basic)6.95ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area62.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity79.72 m³·mol⁻¹ChemAxon
Polarizability31.7 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC17H21NO4
IUPAC name9-methyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-7-yl 3-hydroxy-2-phenylpropanoate
InChI IdentifierInChI=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
InChI KeySTECJAGHUSJQJN-UHFFFAOYSA-N
Isomeric SMILESCN1C2CC(CC1C1OC21)OC(=O)C(CO)C1=CC=CC=C1
Average Molecular Weight303.3529
Monoisotopic Molecular Weight303.147058165
Classification
Description Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Beta-hydroxy acid
  • Monocyclic benzene moiety
  • Morpholine
  • Oxazinane
  • Piperidine
  • N-alkylpyrrolidine
  • Benzenoid
  • Pyrrolidine
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Tertiary amine
  • Tertiary aliphatic amine
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxirane
  • Ether
  • Monocarboxylic acid or derivatives
  • Primary alcohol
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Amine
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSScopolamine, 1 TMS, GC-MS Spectrumsplash10-0f7c-7900000000-28f924e821203772c1adSpectrum
Predicted GC-MSScopolamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-4910000000-24c90e50ab88ad57e82cSpectrum
Predicted GC-MSScopolamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSScopolamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0zg0-0906000000-b30eea7d665eb91b4a232012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0079-3900000000-28a80461ae247a438c752012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udi-9800000000-af7100d0d1c7bc27c4742012-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0019000000-cc4ab81a673ee149c93e2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0429000000-48f2a2d6a6bb3fbcd8372021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-6910000000-719e539fec930d736ea52021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-0904000000-0366209ad3f767f887362021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f79-1900000000-bd791764fd2502fdc39d2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gb9-2910000000-c7c4ffc22c1425ab3dbd2021-10-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Spectrum
ChemSpider ID10194106
ChEMBL IDCHEMBL569713
KEGG Compound IDC01851
Pubchem Compound ID5184
Pubchem Substance IDNot Available
ChEBI ID16794
Phenol-Explorer IDNot Available
DrugBank IDDB00747
HMDB IDHMDB03573
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDScopolamine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference