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

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ChEBI Name (1R,2S)-nortilidine
ChEBI ID CHEBI:77841
ChEBI ASCII Name (1R,2S)-nortilidine
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C16H21NO2
Net Charge 0
Average Mass 259.34340
Monoisotopic Mass 259.15723
InChI InChI=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
InChIKey PDJZPNKVLDWEKI-GOEBONIOSA-N
SMILES CCOC(=O)[C@]1(CCC=C[C@@H]1NC)c1ccccc1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): drug metabolite

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.
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ChEBI Ontology
Outgoing (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 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 Sources
(−)-nortilidine ChEBI
(1R,2S)-(−)-nortilidine ChEBI
ethyl trans-(−)-2-(methylamino)-1-phenyl-3-cyclohexene-1-carboxylate ChEBI
Last Modified
20 March 2014