MR-2096

MR-2096 is a relatively weak opioid analgesic. It has an unusual chiral tetrahydrofuran-2-ylmethyl substitution on the nitrogen which determines the character of effects and toxicity, with the (R) enantiomer MR-2096 being an opioid agonist, while the (S) enantiomer MR-2097 has similarly potent opioid antagonist effects. This substitution makes MR 2096 completely synthetic. It does not require the use of any opium derivatives to produce. This mix of activities has made these two enantiomers useful for characterising the binding site of the mu opioid receptor. It was never marketed due to its high toxicity. [1]

MR-2096
Identifiers
IUPAC name
  • (4R,4aS,7aR,12bS)-4a,9-dihydroxy-3-([(R)-tetrahydrofuran-2-yl]methyl)-2,3,4,4a,5,6-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)one
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H25NO5
Molar mass371.433 g·mol−1
3D model (JSmol)
SMILES
  • O[C@]1([C@H]2C3)[C@@]4(CCN2C[C@H]5CCCO5)C6=C3C=CC(O)=C6O[C@H]4C(CC1)=O
InChI
  • InChI=1S/C21H25NO5/c23-14-4-3-12-10-16-21(25)6-5-15(24)19-20(21,17(12)18(14)27-19)7-8-22(16)11-13-2-1-9-26-13/h3-4,13,16,19,23,25H,1-2,5-11H2/t13-,16-,19+,20+,21-/m1/s1
  • Key:JZVPTJLHOJSOLQ-JAYNPZNESA-N

See also

References
  1. Ramabadran K, Jen MF (April 1985). "Opioid agonist and antagonist properties of diastereoisomeric N-tetrahydronoroxymorphones in mice". Archives Internationales de Pharmacodynamie et de Therapie. 274 (2): 180–8. PMID 4040738.
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