Discuss This Drug

dextilidine

CHEBI:CHEBI_77822

Definition

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).

Chemical Information

Molecular Formula
C17H23NO2
Molecular Mass
273.37000
Charge
0
SMILES
CCOC(=O)[C@@]1(CCC=C[C@H]1N(C)C)c1ccccc1
InChI
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
InChIKey
WDEFBBTXULIOBB-WBVHZDCISA-N

Alternative Names

  • (+)-(1S,2R)-ethyl-2-dimethylamino-1-phenyl-3-cyclohexen-1-carboxylate
  • (+)-ethyl trans-2-(dimethylamino)-1-phenyl-3-cyclohexene-1-carboxylate
  • (1S,2R)-(+)-ethyl-2-dimethylamino-1-phenyl-3-cyclohexen-1-carboxylate
  • dextilidina
  • dextilidine
  • dextilidinum
  • ethyl (1S,2R)-2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate

Drug Classification

Important Medical Information

⚕️ This information is sourced from ChEBI (Chemical Entities of Biological Interest) database and is intended for educational purposes only.

  • Always consult with a healthcare professional before starting, stopping, or modifying any medication.
  • Side effects may vary and this list may not be comprehensive.
  • Drug interactions may occur with other medications.

Additional Identifiers

oboInOwl#hasDbXref
CAS:32447-90-8
core#notation
CHEBI:77822

Additional References

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Additional Attributes

chebi#is_enantiomer_of
http://purl.obolibrary.org/obo/CHEBI_77821
BFO_0000051
http://purl.obolibrary.org/obo/CHEBI_77823
owl#annotatedSource
t297125
owl#someValuesFrom
t296932
oboInOwl#hasOBONamespace
chebi_ontology
oboInOwl#hasDbXref
CAS:32447-90-8
oboInOwl#id
CHEBI:77822
core#notation
CHEBI:77822
oboInOwl#inSubset
http://purl.obolibrary.org/obo/chebi#3_STAR
RO_0000087
http://purl.obolibrary.org/obo/CHEBI_50266
22-rdf-syntax-ns#type
http://www.w3.org/2002/07/owl#Class