2,5-Dimethoxy-4-Methylphenethylamine (2C-D) (CHEM045897)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 13:47:53 UTC
Update Date2016-11-09 01:23:26 UTC
Accession NumberCHEM045897
Identification
Common Name2,5-Dimethoxy-4-Methylphenethylamine (2C-D)
ClassSmall Molecule
Description2C-D (2,5-dimethoxy-4-methylphenethylamine or 2C-M) is a psychedelic drug of the 2C family that is sometimes used as an entheogen. It was first synthesized in 1970 by a team from the Texas Research Institute of Mental Sciences, and its activity was subsequently investigated in humans by Alexander Shulgin. In his book PiHKAL, Shulgin lists the dosage range as being from 20 to 60 mg.Not much information is known about the toxicity of 2C-D, as no major studies have been conducted. According to Shulgin, the effects of 2C-D typically last for 4–6 hours. Shulgin himself referred to this substance as a “pharmacological tofu,” meaning that when mixed with other substances, it can extend or potentiate their effects without coloring the experience too much, in a manner similar to how tofu absorbs the flavors of sauces or spices it is cooked with. Hanscarl Leuner, working in Germany, explored the use of 2C-D under the name LE-25 in psychotherapeutic research.
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2,5-Dimethoxy-4-methyl-beta-phenethylamineMeSH
2,5-DMP CPDMeSH
Chemical FormulaC11H17NO2
Average Molecular Mass195.262 g/mol
Monoisotopic Mass195.126 g/mol
CAS Registry Number24333-19-5
IUPAC Name2-(2,5-dimethoxy-4-methylphenyl)ethan-1-amine
Traditional Name2-(2,5-dimethoxy-4-methylphenyl)ethanamine
SMILESCOC1=CC(CCN)=C(OC)C=C1C
InChI IdentifierInChI=1S/C11H17NO2/c1-8-6-11(14-3)9(4-5-12)7-10(8)13-2/h6-7H,4-5,12H2,1-3H3
InChI KeyUNQQFDCVEMVQHM-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
  • P-dimethoxybenzene
  • Dimethoxybenzene
  • Phenethylamine
  • Phenoxy compound
  • Anisole
  • 2-arylethylamine
  • Phenol ether
  • Alkyl aryl ether
  • Aralkylamine
  • Toluene
  • 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 DescriptorsNot Available
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 Solubility0.64 g/LALOGPS
logP1.33ALOGPS
logP1.59ChemAxon
logS-2.5ALOGPS
pKa (Strongest Basic)9.71ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area44.48 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.25 m³·mol⁻¹ChemAxon
Polarizability22.26 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-359f4a617a7c97a70b57Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-1900000000-ab4ff2b6e4a9d690f729Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00rj-8900000000-873665b622ccc54d367dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-1f680010193119590444Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-647b4ef651f883f9409aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fft-3900000000-5c145872a0f4761c93a4Spectrum
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 IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia Link2C-D
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID135740
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available