mescaline (CHEM043760)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 11:14:39 UTC
Update Date2016-11-09 01:22:59 UTC
Accession NumberCHEM043760
Identification
Common Namemescaline
ClassSmall Molecule
DescriptionA phenethylamine alkaloid that is phenethylamine substituted at positions 3, 4 and 5 by methoxy groups.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Amino-2-(3,4,5-trimethoxyphenyl)ethaneChEBI
3,4,5-TrimethoxybenzeneethanamineChEBI
3,4,5-TrimethoxyphenethylamineChEBI
3,4,5-TrimethoxyphenylethylamineChEBI
MescalinChEBI
MescalinaChEBI
MeskalinChEBI
MezcalinaChEBI
TMPEAChEBI
MezcalinMeSH
PeyoteMeSH
TrimethoxyphenethylamineMeSH
Chemical FormulaC11H17NO3
Average Molecular Mass211.261 g/mol
Monoisotopic Mass211.121 g/mol
CAS Registry Number54-04-6
IUPAC Name2-(3,4,5-trimethoxyphenyl)ethan-1-amine
Traditional Namemescaline
SMILESCOC1=CC(CCN)=CC(OC)=C1OC
InChI IdentifierInChI=1S/C11H17NO3/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3
InChI KeyRHCSKNNOAZULRK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentPhenethylamines
Alternative Parents
Substituents
  • Phenethylamine
  • Phenoxy compound
  • Anisole
  • 2-arylethylamine
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • Aralkylamine
  • Ether
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Amine
  • Primary amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.21 g/LALOGPS
logP0.91ALOGPS
logP0.91ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)9.77ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area53.71 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity58.68 m³·mol⁻¹ChemAxon
Polarizability23.1 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-6910000000-63b875b68510f431304aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-0890000000-616863bde223b3ac872cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0920000000-47fd07c5573212e7fc36Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-5900000000-15a76f5868097c4890edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-fd2ca69e6cdbbf1a0a0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0890000000-83e2781633dd51c42f35Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-2900000000-67896f160b9a42f4f333Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0910000000-9a24a439b17db5331dfbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-501fa4dae613a2963687Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ktb-3900000000-7dc0298d7f673f65aa0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-f0203d0d15365b0c0653Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0590000000-c63f9b5dcd00541ee2ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-9400000000-76523f7fb050748dbc11Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0254474
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00001419
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMescaline
Chemspider ID3934
ChEBI ID28346
PubChem Compound IDNot Available
Kegg Compound IDC06546
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=14516493
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20890669
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22251567
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22900815
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=25036425