ContaminantDB: tilidin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-06-03 11:24:44 UTC

Update Date

2026-04-14 19:32:34 UTC

Accession Number

CHEM043895

Identification

Common Name

tilidin

Class

Small Molecule

Description

An 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 Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-(1S,2R)-Ethyl-2-dimethylamino-1-phenyl-3-cyclohexen-1-carboxylate	ChEBI
(+)-Ethyl trans-2-(dimethylamino)-1-phenyl-3-cyclohexene-1-carboxylate	ChEBI
(1S,2R)-(+)-Ethyl-2-dimethylamino-1-phenyl-3-cyclohexen-1-carboxylate	ChEBI
Dextilidina	ChEBI
Dextilidinum	ChEBI
(+)-(1S,2R)-Ethyl-2-dimethylamino-1-phenyl-3-cyclohexen-1-carboxylic acid	Generator
(+)-Ethyl trans-2-(dimethylamino)-1-phenyl-3-cyclohexene-1-carboxylic acid	Generator
(1S,2R)-(+)-Ethyl-2-dimethylamino-1-phenyl-3-cyclohexen-1-carboxylic acid	Generator
Tilidine hydrochloride, (+-)-211trans	MeSH
Tilidin godecke	MeSH
Valerone	MeSH
Godecke, tilidin	MeSH
Hydrochloride, tilidine	MeSH
Valoron	MeSH
Tilidine hydrochloride	MeSH
Godecke brand OF tilidine hydrochloride hemihydrate	MeSH
Tilidate	MeSH
Tilidine hydrochloride, (+)-trans	MeSH
Tilidine	MeSH

Chemical Formula

C₁₇H₂₃NO₂

Average Molecular Mass

273.376 g/mol

Monoisotopic Mass

273.173 g/mol

CAS Registry Number

20380-58-9

IUPAC Name

ethyl (1S,2R)-2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate

Traditional Name

ethyl (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 Identifier

InChI=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 Key

WDEFBBTXULIOBB-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.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Aralkylamines

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

ethyl 2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate (CHEBI:77822 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.18 g/L	ALOGPS
logP	3.16	ALOGPS
logP	3.35	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	8.6	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.54 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	82.16 m³·mol⁻¹	ChemAxon
Polarizability	30.82 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9320000000-82e133a0dbc5f6946c05	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0090000000-549281aa0b1155af0315	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0h6s-3590000000-007ff8e16a196484312f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0k96-9520000000-cbc61d8b586aef0ec9e9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-2d94511a58089153f832	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0umi-1290000000-0a195aeae1a84976ef2b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ul0-3950000000-dada302b3cdf7206624c	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB13787

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Tilidine

Chemspider ID

Not Available

ChEBI ID

77822

PubChem Compound ID

30131

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

tilidin (CHEM043895)

Structure for CHEM043895: tilidin