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Showing toxin card for Scopolamine (T3D2877)

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Version 1.0
Creation Date 2009-07-21 20:27:33
Update Date 2010-05-18 21:00:36
Accession Number T3D2877
Name Scopolamine
Compound Type
  • Adjuvant
  • Adjuvant, Anesthesia
  • Antimuscarinic
  • Antispasmodic
  • Cholinergic Antagonist
  • Drug
  • Muscarinic Antagonist
  • Mydriatic
Description Scopolamine is 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. [PubChem]
Synonyms
  1. (+)-hyoscine
  2. (+)-scopolamine
  3. (-)-hyoscine
  4. (-)-hyoscine hydrobromide
  5. (-)-scopolamine bromide
  6. (-)-scopolamine hydrobromide
  7. 6,7-Epoxytropine Tropate
  8. 6-b,7-b-Epoxy-3-a-tropanyl S-(-)-tropate
  9. 9-methyl-3-oxa-9-azatricyclo[3.3.1.0~2,4~]non-7-yl tropate
  10. Atrochin
  11. Atroquin
  12. Beldavrin
  13. Buscopan
  14. Buscopan Inj
  15. Buscopan Tab
  16. Epoxytropine tropate
  17. Euscopol
  18. Hydroscine hydrobromide
  19. Hyosceine
  20. Hyoscine
  21. Hyoscine bromide
  22. Hyoscine butylbromide injection sandoz standard
  23. Hyoscine hydrobromide
  24. Hyoscyine hydrobromide
  25. Hyosol
  26. Hysco
  27. Isopto hyoscine
  28. Isoscopil
  29. Kwells
  30. L-hyoscine hydrobromide
  31. L-scopolamine
  32. L-scopolamine-hydrobromide
  33. Methscopolamine bromide
  34. Oscine
  35. Pamine
  36. S-(-)-tropate
  37. SCOP
  38. SEE
  39. Scopamin
  40. Scopine tropate
  41. Scopoderm-TTS
  42. Scopolamine (hyoscine)
  43. Scopolamine bromide
  44. Scopolamine hydrobromide
  45. Scopolaminium bromide
  46. Scopolammonium bromide
  47. Skopolamin
  48. Tranaxine
  49. Transcop
  50. Transderm scop
  51. Transderm-scop
  52. Transderm-v
Chemical IUPAC Name 9-methyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-7-yl 3-hydroxy-2-phenylpropanoate
Chemical Formula C17H21NO4
Chemical Structure Structure
CAS Registry Number 6533-68-2
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
InChI Key InChIKey=STECJAGHUSJQJN-UHFFFAOYSA-N
PubChem Compound ID 5184 Link Image
KEGG ID C01851 Link Image
UniProt ID Not Available
OMIM ID Not Available
ChEBI ID 16794 Link Image
BioCyc ID SCOPOLAMINE Link Image
SuperToxic ID Not Available
CTD ID Not Available
Stitch ID Scopolamine Link Image
DrugBank ID DB00747 Link Image
PDB ID Not Available
ACToR ID Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Scopolamine Link Image
Monoisotopic Mass 303.147058
MOL File Show
PDB File Show
SDF File Show
SMILES CN1C2CC(CC1C1OC21)OC(=O)C(CO)C1=CC=CC=C1
Appearance Not Available
Melting Point 59 oC
Solubility Not Available
Predicted LogP 0.895
Route of Exposure Parental (intravenous, intramuscular, and transdermal); oral
Mechanism of Action Scopolamine acts by interfering with the transmission of nerve impulses by acetylcholine in the parasympathetic nervous system (specifically the vomiting center).
Metabolism Not Available
Toxicity Values Not Available
Lethal Dose Not Available
Carcinogenicity (IARC Classification) Not Available
Uses/Sources Not Available
Minimum Risk Level Not Available
Health Effects Not Available
Symptoms Not Available
Treatment Not Available
General References
  • U321 - Drugs.com
Targets
  1. Muscarinic acetylcholine receptor M1
Target 1 [top]
Target 1 ID 638
Target 1 Name Muscarinic acetylcholine receptor M1
Target 1 Mechanism of Action Scopolamine acts by interfering with the transmission of nerve impulses by acetylcholine in the parasympathetic nervous system (specifically the vomiting center).
Target 1 Description 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
Target 1 Synonyms Not Available
Target 1 Gene Name CHRM1
Target 1 Protein Sequence >Muscarinic acetylcholine receptor M1 
MNTSAPPAVSPNITVLAPGKGPWQVAFIGITTGLLSLATVTGNLLVLISFKVNTELKTVN
NYFLLSLACADLIIGTFSMNLYTTYLLMGHWALGTLACDLWLALDYVASNASVMNLLLIS
FDRYFSVTRPLSYRAKRTPRRAALMIGLAWLVSFVLWAPAILFWQYLVGERTVLAGQCYI
QFLSQPIITFGTAMAAFYLPVTVMCTLYWRIYRETENRARELAALQGSETPGKGGGSSSS
SERSQPGAEGSPETPPGRCCRCCRAPRLLQAYSWKEEEEEDEGSMESLTSSEGEEPGSEV
VIKMPMVDPEAQAPTKQPPRSSPNTVKRPTKKGRDRAGKGQKPRGKEQLAKRKTFSLVKE
KKAARTLSAILLAFILTWTPYNIMVLVSTFCKDCVPETLWELGYWLCYVNSTINPMCYAL
CNKAFRDTFRLLLLCRWDKRRWRKIPKRPGSVHRTPSRQC
Target 1 Number of Residues 460
Target 1 Molecular Weight 51420.4
Target 1 Theoretical pI 9.67
Target 1 GO Classification
Function
amine receptor activity
muscarinic acetylcholine receptor activity
signal transducer activity
receptor activity
transmembrane receptor activity
G-protein coupled receptor activity
rhodopsin-like receptor activity
Process
cellular process
cell communication
signal transduction
cell surface receptor linked signal transduction
G-protein coupled receptor protein signaling pathway
Component
cell
membrane
intrinsic to membrane
integral to membrane
Target 1 General Function Involved in muscarinic acetylcholine receptor activity
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 25-47
  • 62-82
  • 100-121
  • 142-164
  • 187-209
  • 367-387
  • 402-421
Target 1 Essentiality Non Essential
Target 1 Domain Function PF00001:7tm_1
Target 1 GenBank ID Protein Not Available
Target 1 UniProtKB ID P11229 Link Image
Target 1 Cellular Location Cell membrane
Target 1 Gene Sequence Not Available
Target 1 GenBank Gene ID Not Available
Target 1 GeneCard ID CHRM1 Link Image
Target 1 GenAtlas ID CHRM1 Link Image
Target 1 HGNC ID HGNC:1950 Link Image
Target 1 Chromosome Location Chromosome:11
Target 1 Locus 11q13
Target 1 SNPs SNPJam Report Link Image
Target 1 Toxin References
  • U322 - Murasaki O, Kaibara M, Nagase Y, Mitarai S, Doi Y, Sumikawa K, Taniyama K: Site of action of the general anesthetic propofol in muscarinic M1 receptor-mediated signal transduction. J Pharmacol Exp Ther. 2003 Dec;307(3):995-1000. Epub 2003 Oct 8. [PubMed Link Image]
Target 1 General References 3697105; 2336407; 3443095; 15489334; 1445347; 15086532

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