(1S,2R)-nortilidine (CHEBI:77839)

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ChEBI Name	(1S,2R)-nortilidine

ChEBI ID	CHEBI:77839

ChEBI ASCII Name	(1S,2R)-nortilidine

Definition	A ethyl 2-(methylamino)-1-phenylcyclohex-3-ene-1-carboxylate that is dextilidine in which one of the methyl groups attached to the nitrogen is replaced by hydrogen. Dextilidine is a prodrug for (1S,2R)-nortilidine, being metabolised to it by the liver.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

Download	Molfile XML SDF

Formula

C16H21NO2

Net Charge

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+/m1/s1

InChIKey

PDJZPNKVLDWEKI-ZBFHGGJFSA-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 opioid analgesic A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.

Application(s):	opioid analgesic A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.

ChEBI Ontology
Outgoing	(1S,2R)-nortilidine (CHEBI:77839) has role drug metabolite (CHEBI:49103) (1S,2R)-nortilidine (CHEBI:77839) has role opioid analgesic (CHEBI:35482) (1S,2R)-nortilidine (CHEBI:77839) is a ethyl 2-(methylamino)-1-phenylcyclohex-3-ene-1-carboxylate (CHEBI:77835) (1S,2R)-nortilidine (CHEBI:77839) is enantiomer of (1R,2S)-nortilidine (CHEBI:77841)

Incoming	rac-nortilidine (CHEBI:77829) has part (1S,2R)-nortilidine (CHEBI:77839) (1R,2S)-nortilidine (CHEBI:77841) is enantiomer of (1S,2R)-nortilidine (CHEBI:77839)

IUPAC Name

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

Synonyms	Sources
(+)-nortilidine	ChemIDplus
(1S,2R)-(+)-nortilidine	ChEBI
ethyl trans-(+)-2-(methylamino)-1-phenyl-3-cyclohexene-1-carboxylate	ChemIDplus

Last Modified

20 March 2014