N,N-Dimethyl-1,2-diphenylethanamine (CHEM019287)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:59:12 UTC
Update Date2016-11-09 01:15:58 UTC
Accession NumberCHEM019287
Identification
Common NameN,N-Dimethyl-1,2-diphenylethanamine
ClassSmall Molecule
DescriptionLefetamine (Santenol) is a drug which is a stimulant and also an analgesic with effects comparable to codeine. Lefetamine-related 1,2-diphenylethylamines were invented in the 1940s and showed weak analgesic activity.It was investigated in Japan in 1950s. The l-isomer showed weak analgesic action comparable to codeine and antitussive action far weaker than codeine. The d-isomer showed no such activity but caused seizures in rats.It was abused in Japan during the 1950s. In a small study in 1989 it showed some effect against opioid withdrawal symptoms without causing withdrawal symptoms itself. It was concluded that it may be an opioid partial agonist.It has been abused in Europe, in 1989 a small study of 15 abusers and some volunteers found, that it had some partial similarity to opioids, that it produced withdrawal symptoms and had dependence and abuse potential to a certain degree.In a small study in 1994, it was compared to clonidine and buprenorphine in the detoxification of methadone patients and found to be inferior to both of them.Regulation may vary; it does not appear as either a Narcotic or Non-Narcotic under the US Controlled Substances Act 1970 The Canadian Controlled Drugs and Substances Act was amended in 2016 to include the substance as a Schedule III substance. Possession without legal authority can result in maximum 3 years imprisonment. Further, Health Canada amended the Food and Drug Regulations in May, 2016 to classify Lefetamine as a controlled drug.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Lephetamine, hydrochlorideMeSH
1,2-Diphenyl-1-dimethylaminoethane hydrochlorideMeSH
Lephetamine hydrochloride, (R)-(-)-isomerMeSH
LephetamineMeSH
Chemical FormulaC16H19N
Average Molecular Mass225.335 g/mol
Monoisotopic Mass225.152 g/mol
CAS Registry Number6319-84-2
IUPAC Name[(1R)-1,2-diphenylethyl]dimethylamine
Traditional Namelefetamine
SMILES[H][C@](CC1=CC=CC=C1)(N(C)C)C1=CC=CC=C1
InChI IdentifierInChI=1S/C16H19N/c1-17(2)16(15-11-7-4-8-12-15)13-14-9-5-3-6-10-14/h3-12,16H,13H2,1-2H3/t16-/m1/s1
InChI KeyYEJZJVJJPVZXGX-MRXNPFEDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Amphetamine or derivatives
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen 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 Solubility0.045 g/LALOGPS
logP3.4ALOGPS
logP3.99ChemAxon
logS-3.7ALOGPS
pKa (Strongest Basic)9.23ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity73.64 m³·mol⁻¹ChemAxon
Polarizability26.75 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0290000000-9591aebe78fa127f3c19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003r-3940000000-178dd670eb0bede32b09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9500000000-0f5aef0630f656acce9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-5eb08a346ffa79236fd2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0290000000-adfcd36cc98c32ecb744Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001l-3910000000-854960562235e287396aSpectrum
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 LinkLefetamine
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID443970
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available