Nortilidine

Nortilidine^[1] is the major active metabolite of tilidine. It is formed from tilidine by demethylation in the liver. The racemate has opioid analgesic effects roughly equivalent in potency to that of morphine.^[2] The (1R,2S)-isomer has NMDA antagonist activity. The drug also acts as a dopamine reuptake inhibitor.^[3] The reversed-ester of nortilidine is also known, as is the corresponding analogue with the cyclohexene ring replaced by cyclopentane,^[4] which have almost identical properties to nortilidine.^[5]

Nortilidine

Identifiers
IUPAC name ethyl (1R,2S)-2-(methylamino)-1-phenylcyclohex-3-ene-1-carboxylate
CAS Number	38677-94-0
PubChem CID	162321
ChemSpider	142535
UNII	7145G6817J
ChEBI	CHEBI:77839 Y
ChEMBL	ChEMBL1614654
CompTox Dashboard (EPA)	DTXSID10191256
Chemical and physical data
Formula	C16H21NO2
Molar mass	259.349 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCOC(=O)[C@]1(CCC=C[C@@H]1NC)C2=CC=CC=C2
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 Key:PDJZPNKVLDWEKI-GOEBONIOSA-N

Use

Nortilidine has been sold as a designer drug, first being identified in Poland in May 2020.^[6][7]

See also

• Desmetramadol, another opioid metabolite with additional (non-opioid) mechanisms of analgesia, which has also been sold as a designer drug
• Tapentadol