Nortilidine

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Systematic (IUPAC) name
ethyl (1R,2S)-2-(methylamino)-1-phenylcyclohex-3-ene-1-carboxylate
Clinical data
Legal status ?
Identifiers
CAS number 38677-94-0
ATC code ?
ChEMBL CHEMBL1614654
Chemical data
Formula C16H21NO2 
Mol. mass 259.3434 g/mol

Nortilidine[1] is the active metabolite of the drug 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] but virtually all of the opioid activity resides in the (1S,2R) isomer.[3] The (1R,2S) isomer has NMDA antagonist activity. The drug also acts as a dopamine reuptake inhibitor.

See also

  • O-desmethyltramadol

References

  1. US Patent 3792080 - Process for Substituted Cyclohexenes its Products
  2. J Clin Pharmacol. 2002 Nov ;42 (11):1257-61 - Sequential first-pass metabolism of nortilidine: the active metabolite of the synthetic opioid drug tilidine
  3. Opiates: George R. Lenz page 439, Table 9-30 (78)
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