Showing Compound Card for Muscarine (CDB000359)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferences Show 5 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:32:49 UTC
Updated at2020-11-18 16:35:06 UTC
CannabisDB IDCDB000359
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameMuscarine
DescriptionMuscarine or (2S,4R,5S)-Muscarine, L-(+)-muscarine, belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. Muscarine is also a quaternary ammonium salt that is soluble in water. Muscarine is also a proto alkaloid, a class of nitrogenous organic compounds of plant origin with pronounced effects on humans. It is a natural product of some mushroom species, particularly in the genera Inocybe and Clitocybe (PMID: 27714029 ). Muscarine is also found in cannabis plants (PMID: 6991645 ). Muscarine can cause profound activation of the peripheral parasympathetic nervous system that may end in circulatory collapse and death. Muscarine is a nonselective agonist of the muscarinic acetylcholine receptors. Muscarine and muscarine agonists are used for the treatment of glaucoma, urinary retention, postoperative ileus, xerostomia and congenital megacolon. However, muscarine and its agonists are contraindicated for those who are sensitive to parasympathetic stimulation such as people with asthma, Chronic Obstructive Pulmonary disease (COPD), peptic ulcer disease or those with obstructions to the gastrointestinal tract or urinary tract. Muscarine is not metabolized by the body and is removed by renal clearance.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
MuscarinChEMBL
L-(+)-MuscarineChEMBL
Chemical FormulaC9H20NO2
Average Molecular Weight174.26
Monoisotopic Molecular Weight174.1489
IUPAC Name{[(2S,4R,5S)-4-hydroxy-5-methyloxolan-2-yl]methyl}trimethylazanium
Traditional Name(+)-muscarine
CAS Registry Number300-54-9
SMILES
C[C@@H]1O[C@H](C[N+](C)(C)C)C[C@H]1O
InChI Identifier
InChI=1S/C9H20NO2/c1-7-9(11)5-8(12-7)6-10(2,3)4/h7-9,11H,5-6H2,1-4H3/q+1/t7-,8-,9+/m0/s1
InChI KeyUQOFGTXDASPNLL-XHNCKOQMSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentoses
Alternative Parents
Substituents
  • Pentose monosaccharide
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Tetrahydrofuran
  • Secondary alcohol
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Amine
  • Organic salt
  • Alcohol
  • Organic cation
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-3ALOGPS
logP-4.3ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)14.11ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity59.89 m³·mol⁻¹ChemAxon
Polarizability20.1 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS[(4-Hydroxy-5-methyloxolan-2-yl)methyl]trimethylazanium, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - n/a 17V, positivesplash10-0f9y-6900000000-79763ab7b63262ffe2c22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-00di-0900000000-c226ed17dd770fa6c4112020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-00di-2900000000-67eb26beea6d618ebb7d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-00di-5900000000-4e0964583deb72b35ef62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-05fr-9500000000-a0a0c909b980bb4769c22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 23V, positivesplash10-0a4i-9200000000-be98c82a4035b83f87502020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 25V, positivesplash10-0a4i-9100000000-e8830a6e2498d5ca0b6f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 27V, positivesplash10-0a4i-9000000000-19f49df6db6e4b92cf3d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-0a4l-9000000000-0755c01a97b2a22de4812020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 33V, positivesplash10-0a4l-9000000000-b0b62b0c3630f73427032020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 35V, positivesplash10-052f-9000000000-0a2f7b3f7e5bf0ef5ed32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-052f-9000000000-24069c492c822c8073ed2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-00di-0900000000-e02b9884b570bdfc5d5c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-00di-2900000000-1be2813c25bfaa5cb10c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-05fr-9600000000-cb4c5b9dc39c97a632392020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-0c00-9100000000-2e0e0d8c33dd5405906b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 13V, positivesplash10-0bt9-9000000000-1c66632fe3ec85e7e9b72020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 15V, positivesplash10-0bt9-9000000000-b821cc1b0c3b1409a2a42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 19V, positivesplash10-0a4i-9000000000-4556237f549b235f4c6e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 12V, positivesplash10-014i-4900000000-2e898bb2167bdd163be92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 12V, positivesplash10-0a4i-9000000000-e58e4ee62799955c09392020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0900000000-a0080208160655ea0b732019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-2900000000-9edf94eafe412073184c2019-02-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-9100000000-c8c1131f5df11bfdcd192019-02-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Muscarinic acetylcholine receptor M3CHRM31q43P20309 details
Muscarinic acetylcholine receptor M1CHRM111q13P11229 details
Muscarinic acetylcholine receptor M2CHRM27q31-q35P08172 details
Muscarinic acetylcholine receptor M4CHRM411p12-p11.2P08173 details
Muscarinic acetylcholine receptor M5CHRM515q26P08912 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00001422
Chemspider IDNot Available
KEGG Compound IDC07473
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9308
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Jin Z: Muscarine, imidazole, oxazole and thiazole alkaloids. Nat Prod Rep. 2016 Oct 26;33(11):1268-1317. doi: 10.1039/c6np00067c. [PubMed:27714029 ]
  2. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]