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Scopolamine (PC000761)

Record Information
Version1.0
Creation date2015-10-09 22:32:33 UTC
Update date2017-01-19 02:36:35 UTC
FoodComEx IDPC000761
FoodDB RecordFDB023199
Chemical Information
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
(-)-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
HyoscineChEBI
Hyoscine bromidehmdb
Hyoscine hydrobromidehmdb
Hyoscyine hydrobromidehmdb
Hyosolhmdb
Hyscohmdb
Isopto Hyoscinehmdb
Isoscopilhmdb
Kwellshmdb
L-Hyoscine hydrobromidehmdb
l-Scopolamine-hydrobromidehmdb
Methscopolamine Bromidehmdb
Oscinehmdb
Paminehmdb
S-(-)-Tropatehmdb
Scophmdb
Scopaminhmdb
Scopine (-)-tropateChEBI
Scopine (-)-tropic acidGenerator
Scopine tropatehmdb
Scopolamine bromidehmdb
Scopolamine hydrobromidehmdb
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
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
Chemical Taxonomy
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
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 100 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
Toronto Research Chemicals S200005