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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2019-07-23 06:00:10 UTC
HMDB IDHMDB0014605
Secondary Accession Numbers
  • HMDB14605
Metabolite Identification
Common NameMethylscopolamine
DescriptionMethylscopolamine is only found in individuals that have used or taken this drug. It is a muscarinic antagonist used to study binding characteristics of muscarinic cholinergic receptors. [PubChem]Methscopolamine acts by interfering with the transmission of nerve impulses by acetylcholine in the parasympathetic nervous system (specifically the vomiting center). It does so by acting as a muscarinic antagonist.
Structure
Data?1563861610
SynonymsNot Available
Chemical FormulaC18H24NO4
Average Molecular Weight318.392
Monoisotopic Molecular Weight318.169984677
IUPAC Name(1R,2R,4S,5S,7R)-7-{[(2S)-3-hydroxy-2-phenylpropanoyl]oxy}-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-9-ium
Traditional Name(1R,2R,4S,5S,7R)-7-{[(2S)-3-hydroxy-2-phenylpropanoyl]oxy}-9,9-dimethyl-3-oxa-9-azatricyclo[3.3.1.0^{2,4}]nonan-9-ium
CAS Registry Number155-41-9
SMILES
C[N+]1(C)[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/C18H24NO4/c1-19(2)14-8-12(9-15(19)17-16(14)23-17)22-18(21)13(10-20)11-6-4-3-5-7-11/h3-7,12-17,20H,8-10H2,1-2H3/q+1/t12-,13-,14-,15+,16-,17+/m1/s1
InChI KeyLZCOQTDXKCNBEE-IKIFYQGPSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as beta hydroxy acids and derivatives. These 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
  • Tetraalkylammonium salt
  • Pyrrolidine
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Oxacycle
  • Azacycle
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxirane
  • Ether
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Alcohol
  • Primary alcohol
  • Organic nitrogen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point225 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.013 g/LNot Available
LogP-2.58Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP-1.5ALOGPS
logP-3.3ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)15.15ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area59.06 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity95.63 m³·mol⁻¹ChemAxon
Polarizability33.72 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0900000000-cb28eb5cc55b780e740eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0709000000-bd930f92c560745ef9cbJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0902000000-63352f42e53b4cc50dceJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0h6s-2900000000-4e19702f364be7f0ca18JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00462 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00462 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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:
CHRM3
Uniprot ID:
P20309
Molecular weight:
66127.4
References
  1. Sykes DA, Dowling MR, Charlton SJ: Exploring the mechanism of agonist efficacy: a relationship between efficacy and agonist dissociation rate at the muscarinic M3 receptor. Mol Pharmacol. 2009 Sep;76(3):543-51. doi: 10.1124/mol.108.054452. Epub 2009 Jun 4. [PubMed:19498041 ]
  2. Voigtlander U, Johren K, Mohr M, Raasch A, Trankle C, Buller S, Ellis J, Holtje HD, Mohr K: Allosteric site on muscarinic acetylcholine receptors: identification of two amino acids in the muscarinic M2 receptor that account entirely for the M2/M5 subtype selectivities of some structurally diverse allosteric ligands in N-methylscopolamine-occupied receptors. Mol Pharmacol. 2003 Jul;64(1):21-31. [PubMed:12815157 ]
  3. Saito M, Kazuyama E, Shimizu S, Dimitriadis F, Kinoshita Y, Masuda E, Yamada S, Satoh K: Muscarinic receptors and their mRNAs in type 2 Goto-Kakizaki diabetic rat prostate. Prostate. 2010 Oct 1;70(14):1533-9. doi: 10.1002/pros.21188. [PubMed:20687226 ]
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
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Figueroa KW, Suga H, Ehlert FJ: Investigating the interaction of McN-A-343 with the M muscarinic receptor using its nitrogen mustard derivative and ACh mustard. Br J Pharmacol. 2010 Jul;160(6):1534-49. doi: 10.1111/j.1476-5381.2010.00810.x. [PubMed:20590642 ]
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 adenylate cyclase inhibition
Gene Name:
CHRM2
Uniprot ID:
P08172
Molecular weight:
51714.6
References
  1. Soukup O, Proska J, Binder J, Karasova JZ, Tobin G, Jun D, Marek J, Musilek K, Fusek J, Kuca K: Methylacridinium and its cholinergic properties. Neurotox Res. 2009 Nov;16(4):372-7. doi: 10.1007/s12640-009-9071-8. Epub 2009 Jun 30. [PubMed:19565307 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]