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Record Information
Version3.6
Creation Date2006-08-13 00:44:39 UTC
Update Date2016-02-11 01:06:23 UTC
HMDB IDHMDB03573
Secondary Accession Numbers
  • HMDB14885
Metabolite Identification
Common 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.
Structure
Thumb
Synonyms
ValueSource
(-)-HyoscineChEBI
(-)-ScopolamineChEBI
(1S,3S,5R,6R,7S)-6,7-Epoxytropan-3-yl (2S)-3-hydroxy-2-phenylpropanoateChEBI
6,7-Epoxytropine tropateChEBI
6-beta,7-beta-Epoxy-3-alpha-tropanyl S-(-)-tropateChEBI
alpha-(Hydroxymethyl)benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl esterChEBI
HyoscineChEBI
Scopine (-)-tropateChEBI
Transderm-scopChEBI
(1S,3S,5R,6R,7S)-6,7-Epoxytropan-3-yl (2S)-3-hydroxy-2-phenylpropanoic acidGenerator
6,7-Epoxytropine tropic 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-(-)-tropic acidGenerator
6-β,7-β-epoxy-3-α-tropanyl S-(-)-tropateGenerator
6-β,7-β-epoxy-3-α-tropanyl S-(-)-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
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
Scopine (-)-tropic acidGenerator
(+)-HyoscineHMDB
(+)-ScopolamineHMDB
(-)-Hyoscine hydrobromideHMDB
(-)-Scopolamine bromideHMDB
(-)-Scopolamine hydrobromideHMDB
AtrochinHMDB
AtroquinHMDB
BeldavrinHMDB
BuscopanHMDB
Epoxytropine tropateHMDB
EuscopolHMDB
Hydroscine hydrobromideHMDB
HyosceineHMDB
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 tropateHMDB
Scopolamine bromideHMDB
Scopolamine hydrobromideHMDB
Scopolaminium bromideHMDB
Scopolammonium bromideHMDB
SEEHMDB
TranaxineHMDB
Chemical FormulaC17H21NO4
Average Molecular Weight303.3529
Monoisotopic Molecular Weight303.147058165
IUPAC Name(1R,2R,4S,5S,7R)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0²,⁴]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate
Traditional Nametransderm-scop
CAS Registry Number51-34-3
SMILES
CN1[C@H]2C[C@@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)[C@H](CO)C1=CC=CC=C1
InChI Identifier
InChI=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/t11-,12-,13-,14+,15-,16+/m1/s1
InChI KeyInChIKey=STECJAGHUSJQJN-FWXGHANASA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylacetic acid derivatives. These are compounds containing a phenylacetic acid moiety, which consists of a phenyl group substituted at the second position by an acetic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetic acid derivatives
Direct ParentPhenylacetic acid derivatives
Alternative Parents
Substituents
  • Phenylacetate
  • Beta-hydroxy acid
  • N-alkylpyrrolidine
  • Piperidine
  • Oxazinane
  • Morpholine
  • Hydroxy acid
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Carboxylic acid ester
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Drug
  • Plant
Biofunction
  • Adjuvants
  • Adjuvants, Anesthesia
  • Antimuscarinics
  • Antispasmodics
  • Cholinergic Antagonists
  • Muscarinic Antagonists
  • Mydriatics
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point59 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility100 mg/mLNot Available
LogP0.98SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility6.61 mg/mLALOGPS
logP1.4ALOGPS
logP0.89ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)15.15ChemAxon
pKa (Strongest Basic)6.95ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area62.3 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity79.72 m3·mol-1ChemAxon
Polarizability31.41 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
Tissue Location
  • Adipose Tissue
  • Brain
  • Nerve Cells
  • Neuron
  • Stratum Corneum
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.021 (0.00021-0.043) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00747
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023199
KNApSAcK IDNot Available
Chemspider ID10194106
KEGG Compound IDC01851
BioCyc IDSCOPOLAMINE
BiGG IDNot Available
Wikipedia LinkScopolamine
NuGOwiki LinkHMDB03573
Metagene LinkHMDB03573
METLIN ID3433
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID16794
References
Synthesis ReferenceChemnitius, F. Method for the technical preparation of scopolamine. Journal fuer Praktische Chemie (Leipzig) (1928), 120 221-4.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Lee HW, Park WS, Kim YW, Cho SH, Kim SS, Seo JH, Lee KT: A rapid and sensitive liquid chromatography/positive ion tandem mass spectrometry method for the determination of cimetropium in human plasma by liquid-liquid extraction. J Mass Spectrom. 2006 Jul;41(7):855-60. [16810649 ]
  2. Blin J, Piercey MF, Giuffra ME, Mouradian MM, Chase TN: Metabolic effects of scopolamine and physostigmine in human brain measured by positron emission tomography. J Neurol Sci. 1994 May;123(1-2):44-51. [8064320 ]
  3. Frey KA, Koeppe RA, Mulholland GK, Jewett D, Hichwa R, Ehrenkaufer RL, Carey JE, Wieland DM, Kuhl DE, Agranoff BW: In vivo muscarinic cholinergic receptor imaging in human brain with [11C]scopolamine and positron emission tomography. J Cereb Blood Flow Metab. 1992 Jan;12(1):147-54. [1727135 ]
  4. Kranke P, Morin AM, Roewer N, Wulf H, Eberhart LH: The efficacy and safety of transdermal scopolamine for the prevention of postoperative nausea and vomiting: a quantitative systematic review. Anesth Analg. 2002 Jul;95(1):133-43, table of contents. [12088957 ]
  5. Hagemann K, Piek K, Stockigt J, Weiler EW: Monoclonal antibody-based enzyme immunoassay for the quantitative determination of the tropane alkaloid, scopolamine. Planta Med. 1992 Feb;58(1):68-72. [1620747 ]
  6. Boumba VA, Mitselou A, Vougiouklakis T: Fatal poisoning from ingestion of Datura stramonium seeds. Vet Hum Toxicol. 2004 Apr;46(2):81-2. [15080209 ]
  7. Rosier A, Cornette L, Orban GA: Scopolamine-induced impairment of delayed recognition of abstract visual shapes. Neuropsychobiology. 1998;37(2):98-103. [9566275 ]
  8. Smith AM, Cadoret G, St-Amour D: Scopolamine increases prehensile force during object manipulation by reducing palmar sweating and decreasing skin friction. Exp Brain Res. 1997 May;114(3):578-83. [9187293 ]
  9. Ebert U, Grossmann M, Oertel R, Gramatte T, Kirch W: Pharmacokinetic-pharmacodynamic modeling of the electroencephalogram effects of scopolamine in healthy volunteers. J Clin Pharmacol. 2001 Jan;41(1):51-60. [11144994 ]
  10. Renner UD, Oertel R, Kirch W: Pharmacokinetics and pharmacodynamics in clinical use of scopolamine. Ther Drug Monit. 2005 Oct;27(5):655-65. [16175141 ]
  11. Gordon C, Ben-Aryeh H, Attias J, Szargel R, Gutman D: Effect of transdermal scopolamine on salivation. J Clin Pharmacol. 1985 Sep;25(6):407-12. [4056076 ]
  12. Fan Y, Hu J, Li J, Yang Z, Xin X, Wang J, Ding J, Geng M: Effect of acidic oligosaccharide sugar chain on scopolamine-induced memory impairment in rats and its related mechanisms. Neurosci Lett. 2005 Feb 21;374(3):222-6. Epub 2004 Dec 10. [15663967 ]
  13. Stetina PM, Madai B, Kulemann V, Kirch W, Joukhadar C: Pharmacokinetics of scopolamine in serum and subcutaneous adipose tissue in healthy volunteers. Int J Clin Pharmacol Ther. 2005 Mar;43(3):134-9. [15792397 ]
  14. Schwarz RD, Callahan MJ, Coughenour LL, Dickerson MR, Kinsora JJ, Lipinski WJ, Raby CA, Spencer CJ, Tecle H: Milameline (CI-979/RU35926): a muscarinic receptor agonist with cognition-activating properties: biochemical and in vivo characterization. J Pharmacol Exp Ther. 1999 Nov;291(2):812-22. [10525104 ]
  15. Suojaranta-Ylinen R, Hendolin H, Tuomisto L: The effects of morphine, morphine plus scopolamine, midazolam and promethazine on cerebrospinal fluid histamine concentration and postoperative analgesic consumption. Agents Actions. 1991 May;33(1-2):212-4. [1897441 ]
  16. Dreyfuss P, Vogel D, Walsh N: The use of transdermal scopolamine to control drooling. A case report. Am J Phys Med Rehabil. 1991 Aug;70(4):220-2. [1878183 ]
  17. Putcha L, Cintron NM, Tsui J, Vanderploeg JM, Kramer WG: Pharmacokinetics and oral bioavailability of scopolamine in normal subjects. Pharm Res. 1989 Jun;6(6):481-5. [2762223 ]

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
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:
51420.4