Nortilidine

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Nortilidine structure.png
Systematic (IUPAC) name
ethyl (1R,2S)-2-(methylamino)-1-phenylcyclohex-3-ene-1-carboxylate
Identifiers
CAS Number 38677-94-0
ChEBI CHEBI:77839 YesY
ChEMBL CHEMBL1614654
Chemical data
Formula C16H21NO2
Molecular mass 259.3434 g/mol
  • O=C(OCC)[C@@]1(CCC=C[C@H]1N(C)C)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+/m1/s1
  • Key:InChIKey=PDJZPNKVLDWEKI-ZBFHGGJFSA-N

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] 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.[4] The reversed-ester of tilidine is also known[5] which has almost identical properties to nortilidine.[6]

See also

References

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  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)
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ US Patent 4291059 - Cycloaromatic compounds, analgesic Properties thereof and Method of use thereof as analgesic
  6. ↑ Personal Communication with Derek P. Reynolds
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