MR-2096

MR-2096

Systematic (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
Identifiers
CAS Number	62509-10-8
PubChem	CID 5748260
ChemSpider	4677855
Chemical data
Formula	C21H25NO5
Molar mass	371.43 g/mol
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

MR-2096 is an opioid analgesic drug related to oxymorphone. It has an unusual chiral tetrahydrofuran-2-ylmethyl substitution on the nitrogen which determines the character of effects, with the (R) enantiomer MR-2096 being an opioid agonist, while the (S) enantiomer MR-2097 has similarly potent opioid antagonist effects. This mix of activities has made these two enantiomers useful for characterising the binding site of the mu opioid receptor.^[1]

See also

• N-Phenethylnormorphine
• Ro4-1539

References

1. Ramabadran, K.; Jen, M. F. (1985). "Opioid agonist and antagonist properties of diastereoisomeric N-tetrahydronoroxymorphones in mice". Archives Internationales de Pharmacodynamie et de Thérapie 274 (2): 180–188. PMID 4040738.