3,4-dimethoxyphenethylamine (CHEM045244)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 12:58:43 UTC
Update Date2016-11-09 01:23:18 UTC
Accession NumberCHEM045244
Identification
Common Name3,4-dimethoxyphenethylamine
ClassSmall Molecule
DescriptionAn aromatic ether that is the derivative of 2-phenylethylamine with methoxy substituents at the 3- and 4-positions. It is an alkaloid isolated from the Cactaceae family.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-(3,4-Dimethoxy-phenyl)-ethylamineChEBI
3,4-Di-O-methyldopamineChEBI
3,4-Dimethoxy-beta-phenylethylamineChEBI
3,4-DimethoxybenzeneethanamineChEBI
3,4-DimethoxydopamineChEBI
3,4-DimethoxyphenethylamineChEBI
beta-(3,4-Dimethyoxyphenyl)ethylamineChEBI
DimethoxydopamineChEBI
DimethoxyphenylethylamineChEBI
DimethylmescalineChEBI
DIMPEAChEBI
DMPEAChEBI
Dopamine dimethyl etherChEBI
HomoveratrylamineChEBI
O,O-DimethyldopamineChEBI
3,4-Dimethoxy-b-phenylethylamineGenerator
3,4-Dimethoxy-β-phenylethylamineGenerator
b-(3,4-Dimethyoxyphenyl)ethylamineGenerator
Β-(3,4-dimethyoxyphenyl)ethylamineGenerator
2-(3,4-Dimethoxyphenyl)ethanamineHMDB
2-(3,4-Dimethoxyphenyl)ethanamine (acd/name 4.0)HMDB
2-(3,4-Dimethoxyphenyl)ethylamineHMDB
2-(3,4-Dimethoxyphenyl)ethylamine (acd/name 4.0)HMDB
3, 4-Dimethoxy-beta-phenethylamineHMDB
3, 4-Dimethoxy-beta-phenylethylamineHMDB
3, 4-DimethoxybenzeneethanamineHMDB
3, 4-DimethoxyphenethylamineHMDB
3, 4-Dimethoxyphenylethylamine(base)HMDB
3,4-Dimethoxy-benzeneethanamineHMDB
3,4-Dimethoxy-benzenethanamineHMDB
3,4-Dimethoxy-beta-phenethylamineHMDB
3,4-Dimethoxy-phenethylamineHMDB
3,4-DimethoxypheneethylamineHMDB
3,4-Dimethoxyphenylethylamine(base)HMDB
beta-(3,4-Dimethoxyphenyl)ethylamineHMDB
DMPEHMDB
Chemical FormulaC10H15NO2
Average Molecular Mass181.232 g/mol
Monoisotopic Mass181.110 g/mol
CAS Registry Number120-20-7
IUPAC Name2-(3,4-dimethoxyphenyl)ethan-1-amine
Traditional Namedimethoxyphenylethylamine
SMILESCOC1=C(OC)C=C(CCN)C=C1
InChI IdentifierInChI=1S/C10H15NO2/c1-12-9-4-3-8(5-6-11)7-10(9)13-2/h3-4,7H,5-6,11H2,1-2H3
InChI KeyANOUKFYBOAKOIR-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dimethoxybenzenes. These are organic aromatic compounds containing a monocyclic benzene moiety carrying exactly two methoxy groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassMethoxybenzenes
Direct ParentDimethoxybenzenes
Alternative Parents
Substituents
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • Phenethylamine
  • Phenoxy compound
  • Anisole
  • 2-arylethylamine
  • Phenol ether
  • Alkyl aryl ether
  • Aralkylamine
  • Ether
  • Organic nitrogen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • 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 Solubility1.59 g/LALOGPS
logP0.9ALOGPS
logP1.07ChemAxon
logS-2.1ALOGPS
pKa (Strongest Basic)9.8ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area44.48 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity52.21 m³·mol⁻¹ChemAxon
Polarizability20.18 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ue9-7900000000-e258dc3dc0a069f89bd5Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ue9-7900000000-120c686cfb57062addf9Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ue9-8900000000-7b3bb96b7d3241d758d7Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ue9-7900000000-e258dc3dc0a069f89bd5Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ue9-7900000000-120c686cfb57062addf9Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ue9-8900000000-7b3bb96b7d3241d758d7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-6900000000-38d3389596ede8e365b3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0900000000-adbc40a8a0427b3f3fceSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0gb9-1900000000-378f4a1c05d1e1ae78afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lr-0900000000-25ceec6a941bb2399272Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-9a1f680719d4d377cf0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059b-7900000000-ea4cd6aaee62c9a9dcf0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-5499743e5a06328defcdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-0ca8775e2ab7549a7dd6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4900000000-f6e4dbf7311ac479604dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-ae9b23b219381cfbd573Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-0900000000-1d498454bd777cb50d22Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00l6-9600000000-588efb293ab7f45b2f0eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-768c86e8875032c5d486Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0900000000-f77b2997745c83d2f0e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-4900000000-4be1f0b7a8cf6ab03b8bSpectrum
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 IDHMDB0041806
FooDB IDFDB111666
Phenol Explorer IDNot Available
KNApSAcK IDC00042105
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link3,4-dimethoxyphenethylamine
Chemspider ID8114
ChEBI ID136995
PubChem Compound ID8421
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1221818
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21504819
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=3377143
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=5812246
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=7059639
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=8911701
7. Lundstrom J: Biosynthesis of mescaline and 3,4-dimethoxyphenethylamine in Trichocereus pachanoi Br&R. Acta Pharm Suec. 1970 Dec;7(6):651-66.
8. Pummangura S, Nichols DE, McLaughlin JL: Cactus alkaloids XXXIII: beta-phenethylamines from the Guatemalan cactus Pilosocereus maxonii. J Pharm Sci. 1977 Oct;66(10):1485-7. doi: 10.1002/jps.2600661037.
9. Pardanani JH, McLaughlin JL, Kondrat RW, Cooks RG: Cactus alkaloids. XXXVI. Mescaline and related compounds from Trichocereus peruvianus. Lloydia. 1977 Nov-Dec;40(6):585-90.
10. Knoll E, Wisser H, Emrich HM: 3,4-Dimethoxyphenylethylamine excretion of normals and schizophrenics, behaviour during total fasting. Clin Chim Acta. 1978 Nov 1;89(3):493-502. doi: 10.1016/0009-8981(78)90415-1.
11. Keller WJ, Ferguson GG: Effects of 3,4-dimethoxyphenethylamine derivatives on monoamine oxidase. J Pharm Sci. 1977 Jul;66(7):1048-50. doi: 10.1002/jps.2600660741.
12. Koshimura I, Imai H, Hidano T, Endo K, Mochizuki H, Kondo T, Mizuno Y: Dimethoxyphenylethylamine and tetrahydropapaverine are toxic to the nigrostriatal system. Brain Res. 1997 Oct 31;773(1-2):108-16. doi: 10.1016/s0006-8993(97)00922-0.
13. Goto K, Mochizuki H, Hattori T, Nakamura N, Mizuno Y: Neurotoxic effects of papaverine, tetrahydropapaverine and dimethoxyphenylethylamine on dopaminergic neurons in ventral mesencephalic-striatal co-culture. Brain Res. 1997 Apr 18;754(1-2):260-8. doi: 10.1016/s0006-8993(97)00093-0.