Nortilidine

Chemical compound From Wikipedia, the free encyclopedia

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]

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Quick facts Identifiers, CAS Number ...
Nortilidine
Identifiers
  • ethyl (1R,2S)-2-(methylamino)-1-phenylcyclohex-3-ene-1-carboxylate
CAS Number
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ChEBI
ChEMBL
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Chemical and physical data
FormulaC16H21NO2
Molar mass259.349 g·mol−1
3D model (JSmol)
  • CCOC(=O)[C@]1(CCC=C[C@@H]1NC)C2=CC=CC=C2
  • 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
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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

References

External links

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