Record Information |
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Version | 2.0 |
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Creation Date | 2009-07-21 20:27:33 UTC |
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Update Date | 2014-12-24 20:25:52 UTC |
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Accession Number | T3D2877 |
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Identification |
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Common Name | Scopolamine |
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Class | Small Molecule |
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Description | Scopolamine, 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. |
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Compound Type | - Adjuvant
- Adjuvant, Anesthesia
- Amine
- Antimuscarinic
- Antispasmodic
- Cholinergic Antagonist
- Drug
- Ester
- Ether
- Food Toxin
- Metabolite
- Muscarinic Antagonist
- Mydriatic
- Natural Compound
- Organic Compound
- Plant Toxin
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Chemical Structure | |
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Synonyms | Synonym | (+)-Hyoscine | (+)-Scopolamine | (-)-Hyoscine | (-)-Hyoscine hydrobromide | (-)-scopolamine | (-)-Scopolamine bromide | (-)-Scopolamine hydrobromide | (1S,3S,5R,6R,7S)-6,7-epoxytropan-3-yl (2S)-3-hydroxy-2-phenylpropanoate | 6,7-Epoxytropine Tropate | 6-beta,7-beta-Epoxy-3-alpha-tropanyl S-(-)-tropate | alpha-(Hydroxymethyl)benzeneacetic acid 9-methyl-3-oxa-9-azatricyclo(3.3.1.0(2.4))non-7-yl ester | Atrochin | Atroquin | Beldavrin | Buscopan | Epoxytropine tropate | Euscopol | Hydroscine hydrobromide | Hyosceine | Hyoscine | Hyoscine bromide | Hyoscine hydrobromide | Hyoscyine hydrobromide | Hyosol | Hysco | Isopto Hyoscine | Isoscopil | Kwells | L-Hyoscine hydrobromide | L-Scopolamine-hydrobromide | Methscopolamine Bromide | Oscine | Pamine | S-(-)-Tropate | Scop | Scopamin | scopine (-)-tropate | scopine (−)-tropate | Scopine tropate | Scopoderm | Scopolamine bromide | Scopolamine hydrobromide | Scopolaminium bromide | Scopolammonium bromide | SEE | Tranaxine | Transderm-Scop |
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Chemical Formula | C17H21NO4 |
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Average Molecular Mass | 303.353 g/mol |
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Monoisotopic Mass | 303.147 g/mol |
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CAS Registry Number | 51-34-3 |
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IUPAC Name | (1R,2R,4S,5S,7S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate |
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Traditional Name | (1R,2R,4S,5S,7S)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-7-yl (2S)-3-hydroxy-2-phenylpropanoate |
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SMILES | [H][C@](CO)(C(=O)O[C@]1([H])C[C@@]2([H])N(C)[C@@]([H])(C1)[C@]1([H])O[C@]21[H])C1=CC=CC=C1 |
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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 |
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InChI Key | InChIKey=STECJAGHUSJQJN-FWXGHANASA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Hydroxy acids and derivatives |
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Sub Class | Beta hydroxy acids and derivatives |
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Direct Parent | Beta hydroxy acids and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
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Biofluid Locations | Not Available |
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Tissue Locations | - Adipose Tissue
- Brain
- Nerve Cells
- Neuron
- Stratum Corneum
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Pathways | Not Available |
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Applications | |
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Biological Roles | |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | 59°C | Boiling Point | Not Available | Solubility | 1E+005 mg/L | LogP | 0.98 |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | Deposition Date | View |
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GC-MS | GC-MS Spectrum - GC-MS (1 TMS) | splash10-0f7c-7900000000-28f924e821203772c1ad | 2018-05-25 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-00di-4910000000-24c90e50ab88ad57e82c | 2017-09-01 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0006-4900000000-596180a39c76ec0fe1ae | 2017-10-06 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0udi-0009000000-9733effdc3262b114ed6 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0udi-0809000000-a686e4c768aedb57cf8e | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-000i-1901000000-f66f538c7db471e86fd5 | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-000i-3900000000-5eedeba4bedea55de9ad | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0udr-7900000000-1309364bbca3810a6afa | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT , positive | splash10-000i-0900000000-1c1d2f52fb7a5d745e1e | 2017-09-14 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 90V, Positive | splash10-0udi-9700000000-80887cb9e3f0d05c8bf5 | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 90V, Positive | splash10-0udi-9800000000-80887cb9e3f0d05c8bf5 | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 75V, Positive | splash10-0udi-6900000000-010e6e0ca9f0d9f3618b | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 60V, Positive | splash10-0f79-4900000000-a0695c5add6db92de8b2 | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 45V, Positive | splash10-000i-2900000000-887570e409db5eca481c | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 60V, Positive | splash10-0f79-4900000000-5e1feadfe643a530d956 | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 45V, Positive | splash10-000i-2900000000-9556767e32b410cf8d73 | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 15V, Positive | splash10-0udi-0309000000-fda2d2422fa0a3b4172e | 2021-09-20 | View Spectrum | LC-MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-0k9i-0903000000-cc938997b1c67e020c14 | 2021-09-20 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0f79-0955000000-64498c50c4e2afb15c32 | 2016-06-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-1930000000-5d768d7bc9f10614fd97 | 2016-06-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0lxt-4900000000-f39cfd7374383b7b1aaf | 2016-06-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0549000000-2102ba2525a572e05e74 | 2016-08-04 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0uk9-1952000000-23caf7102d633b0031b2 | 2016-08-04 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0hr0-4900000000-854ad2f78678cc2d4db3 | 2016-08-04 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0f6t-0904000000-0366209ad3f767f88736 | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0f79-1900000000-bd791764fd2502fdc39d | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0gb9-2910000000-c7c4ffc22c1425ab3dbd | 2021-09-22 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0019000000-cc4ab81a673ee149c93e | 2021-09-25 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental) | Not Available | 2018-05-25 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | 2021-09-24 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | Not Available | 2018-05-25 | View Spectrum |
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Toxicity Profile |
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Route of Exposure | Parental (intravenous, intramuscular, and transdermal); oral |
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Mechanism of Toxicity | Scopolamine acts by interfering with the transmission of nerve impulses by acetylcholine in the parasympathetic nervous system (specifically the vomiting center). |
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Metabolism |
Route of Elimination: Less than 10% of the total dose is excreted in the urine as parent and metabolites over 108 hours.
Half Life: 4.5 hours |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | For the treatment of excessive salivation, colicky abdominal pain, bradycardia, sialorrhoea, diverticulitis, irritable bowel syndrome and motion sickness. |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB00747 |
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HMDB ID | HMDB03573 |
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PubChem Compound ID | 5184 |
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ChEMBL ID | CHEMBL1201069 |
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ChemSpider ID | 10194106 |
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KEGG ID | C01851 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 16794 |
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BioCyc ID | SCOPOLAMINE |
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CTD ID | Not Available |
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Stitch ID | Scopolamine |
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PDB ID | Not Available |
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ACToR ID | Not Available |
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Wikipedia Link | Scopolamine |
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References |
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Synthesis Reference | Yang Guodong, “Preparation and application of scopolamine and chlorpromazine as a drug-withdrawal agent.” U.S. Patent US5543407, issued February, 1993. |
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MSDS | Link |
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General References | - 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Boumba VA, Mitselou A, Vougiouklakis T: Fatal poisoning from ingestion of Datura stramonium seeds. Vet Hum Toxicol. 2004 Apr;46(2):81-2. [15080209 ]
- Rosier A, Cornette L, Orban GA: Scopolamine-induced impairment of delayed recognition of abstract visual shapes. Neuropsychobiology. 1998;37(2):98-103. [9566275 ]
- 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 ]
- 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 ]
- Renner UD, Oertel R, Kirch W: Pharmacokinetics and pharmacodynamics in clinical use of scopolamine. Ther Drug Monit. 2005 Oct;27(5):655-65. [16175141 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Drugs.com [Link]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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