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CHEBI:77822 - dextilidine

ChEBI IDCHEBI:77822
ChEBI Namedextilidine
Stars
DefinitionAn 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).
Last Modified20 March 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC17H23NO2
Net Charge0
Average Mass273.376
Monoisotopic Mass273.17288
SMILESCCOC(=O)[C@]1(c2ccccc2)CCC=C[C@H]1N(C)C
InChIInChI=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
InChIKeyWDEFBBTXULIOBB-WBVHZDCISA-N
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
opioid analgesic  A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
Applications:
opioid analgesic  A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
prodrug  A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
ChEBI Ontology
Outgoing Relation(s)
dextilidine (CHEBI:77822) has role opioid analgesic (CHEBI:35482)
dextilidine (CHEBI:77822) has role prodrug (CHEBI:50266)
dextilidine (CHEBI:77822) is a ethyl 2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate (CHEBI:77817)
dextilidine (CHEBI:77822) is enantiomer of ent-dextilidine (CHEBI:77821)
Incoming Relation(s)
tilidine (CHEBI:77823) has part dextilidine (CHEBI:77822)
ent-dextilidine (CHEBI:77821) is enantiomer of dextilidine (CHEBI:77822)
IUPAC Name 
ethyl (1S,2R)-2-(dimethylamino)-1-phenylcyclohex-3-ene-1-carboxylate
INNs  Source
dextilidinaWHO MedNet
dextilidineWHO MedNet
dextilidinumWHO MedNet
dextilidineWHO MedNet
Synonyms  Source
(+)-(1S,2R)-ethyl-2-dimethylamino-1-phenyl-3-cyclohexen-1-carboxylateChemIDplus
(+)-ethyl trans-2-(dimethylamino)-1-phenyl-3-cyclohexene-1-carboxylateChemIDplus
(1S,2R)-(+)-ethyl-2-dimethylamino-1-phenyl-3-cyclohexen-1-carboxylateChEBI
Registry NumbersSources
CAS:32447-90-8ChemIDplus