tilidin (CHEM043895)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-06-03 11:24:44 UTC
Update Date2016-11-09 01:23:00 UTC
Accession NumberCHEM043895
Identification
Common Nametilidin
ClassSmall Molecule
DescriptionAn ethyl 2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate that has S configuration at the carbon bearing the phenyl group and R configuration at the carbon bearing the dimethylamino group. The opioid analgesic tilidine is the racemate comprising equimolar amounts of dextilidine and its enantiomer, ent-dextilidine. A prodrug, tilidine is converted by the liver to the active analgesic, nortilidine; virtually all of the opioid activity resides in the (1S,2R) isomer (i.e. the isomer derived from dextilidine).
Contaminant Sources
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+)-(1S,2R)-Ethyl-2-dimethylamino-1-phenyl-3-cyclohexen-1-carboxylateChEBI
(+)-Ethyl trans-2-(dimethylamino)-1-phenyl-3-cyclohexene-1-carboxylateChEBI
(1S,2R)-(+)-Ethyl-2-dimethylamino-1-phenyl-3-cyclohexen-1-carboxylateChEBI
DextilidinaChEBI
DextilidinumChEBI
(+)-(1S,2R)-Ethyl-2-dimethylamino-1-phenyl-3-cyclohexen-1-carboxylic acidGenerator
(+)-Ethyl trans-2-(dimethylamino)-1-phenyl-3-cyclohexene-1-carboxylic acidGenerator
(1S,2R)-(+)-Ethyl-2-dimethylamino-1-phenyl-3-cyclohexen-1-carboxylic acidGenerator
Tilidine hydrochloride, (+-)-211transMeSH
Tilidin godeckeMeSH
ValeroneMeSH
Godecke, tilidinMeSH
Hydrochloride, tilidineMeSH
ValoronMeSH
Tilidine hydrochlorideMeSH
Godecke brand OF tilidine hydrochloride hemihydrateMeSH
TilidateMeSH
Tilidine hydrochloride, (+)-transMeSH
TilidineMeSH
Chemical FormulaC17H23NO2
Average Molecular Mass273.376 g/mol
Monoisotopic Mass273.173 g/mol
CAS Registry Number20380-58-9
IUPAC Nameethyl (1S,2R)-2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate
Traditional Nameethyl (1S,2R)-2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate
SMILES[H][C@]1(C=CCC[C@]1(C(=O)OCC)C1=CC=CC=C1)N(C)C
InChI IdentifierInChI=1S/C17H23NO2/c1-4-20-16(19)17(14-10-6-5-7-11-14)13-9-8-12-15(17)18(2)3/h5-8,10-12,15H,4,9,13H2,1-3H3/t15-,17+/m1/s1
InChI KeyWDEFBBTXULIOBB-WBVHZDCISA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Tertiary amine
  • Tertiary aliphatic amine
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organopnictogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
  • ethyl 2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate (CHEBI:77822 )
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 Solubility0.18 g/LALOGPS
logP3.16ALOGPS
logP3.35ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)8.6ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity82.16 m³·mol⁻¹ChemAxon
Polarizability30.82 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9320000000-82e133a0dbc5f6946c05Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-549281aa0b1155af0315Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0h6s-3590000000-007ff8e16a196484312fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0k96-9520000000-cbc61d8b586aef0ec9e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-2d94511a58089153f832Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0umi-1290000000-0a195aeae1a84976ef2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ul0-3950000000-dada302b3cdf7206624cSpectrum
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 IDDB13787
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 LinkTilidine
Chemspider IDNot Available
ChEBI ID77822
PubChem Compound ID30131
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available