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CHEBI:77841 - (1R,2S)-nortilidine

ChEBI IDCHEBI:77841
ChEBI Name(1R,2S)-nortilidine
Stars
ASCII Name(1R,2S)-nortilidine
DefinitionAn ethyl 2-(methylamino)-1-phenylcyclohex-3-ene-1-carboxylate that is ent-dextilidine in which one of the methyl groups attached to the nitrogen is replaced by hydrogen. ent-Dextilidine is metabolised to (1R,2S)-nortilidine by the liver.
Last Modified20 March 2014
SubmitterGareth Owen
DownloadsMolfile
FormulaC16H21NO2
Net Charge0
Average Mass259.349
Monoisotopic Mass259.15723
SMILESCCOC(=O)[C@@]1(c2ccccc2)CCC=C[C@@H]1NC
InChIInChI=1S/C16H21NO2/c1-3-19-15(18)16(13-9-5-4-6-10-13)12-8-7-11-14(16)17-2/h4-7,9-11,14,17H,3,8,12H2,1-2H3/t14-,16+/m0/s1
InChIKeyPDJZPNKVLDWEKI-GOEBONIOSA-N
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
NMDA receptor antagonist  Any substance that inhibits the action of N-methyl-D-aspartate (NMDA) receptors. They tend to induce a state known as dissociative anesthesia, marked by catalepsy, amnesia, and analgesia, while side effects can include hallucinations, nightmares, and confusion. Due to their psychotomimetic effects, many NMDA receptor antagonists are used as recreational drugs.
ChEBI Ontology
Outgoing Relation(s)
(1R,2S)-nortilidine (CHEBI:77841) has role drug metabolite (CHEBI:49103)
(1R,2S)-nortilidine (CHEBI:77841) has role NMDA receptor antagonist (CHEBI:60643)
(1R,2S)-nortilidine (CHEBI:77841) is a ethyl 2-(methylamino)-1-phenylcyclohex-3-ene-1-carboxylate (CHEBI:77835)
(1R,2S)-nortilidine (CHEBI:77841) is enantiomer of (1S,2R)-nortilidine (CHEBI:77839)
Incoming Relation(s)
rac-nortilidine (CHEBI:77829) has part (1R,2S)-nortilidine (CHEBI:77841)
(1S,2R)-nortilidine (CHEBI:77839) is enantiomer of (1R,2S)-nortilidine (CHEBI:77841)
IUPAC Name 
ethyl (1R,2S)-2-(methylamino)-1-phenylcyclohex-3-ene-1-carboxylate
Synonyms  Source
(−)-nortilidineChEBI
ethyl trans-(−)-2-(methylamino)-1-phenyl-3-cyclohexene-1-carboxylateChEBI
(1R,2S)-(−)-nortilidineChEBI