6S-Nalfurafine

CAS: 152658-36-1

Ref. TR-N255615

Product Information

• Name: 6S-Nalfurafine
• Synonyms: (2E)-N-[(5a,6a)-17-(Cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-yl]-3-(3-furanyl)-N-methyl-2-propenamide, (E)-N-[(5a,6a)-17-(Cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-yl]-3-(3-furanyl)-N-methyl-2-propenamide
• CAS: 152658-36-1

Description

Applications 6S-Nalfurafine is a stereoisomer of Nalfurafine (N255600), a on-narcotic opioid drug for intractable itch caused by hemodialysis. It showed significant opioid κ-agonist activity and induced neither aversion nor preference in rats on the CPP (Conditioned Place Preference) test. Nalfurafine is a new therapeutic agent for the treatment of uremic pruritus in hemodialysis patients.
References Fujii, H., et al.: Bioorg. Med. Chem., 12, 4133 (2004); Mori, T., et al.: Life Sci., 75, 2433 (2004); Fujii, H., et al.: Curr. Med. Chem., 13, 1109 (2006); Nagase, H., et al.: Bioorg. Med. Chem. Lett., 20, 6302 (2010)

• Brand: TRC

Chemical properties

• Molecular weight: 476.56
• Formula: C₂₈H₃₂N₂O₅
• Color/Form: Neat
• InChI: InChI=1S/C28H32N2O5/c1-29(23(32)7-4-18-9-13-34-16-18)20-8-10-28(33)22-14-19-5-6-21(31)25-24(19)27(28,26(20)35-25)11-12-30(22)15-17-2-3-17/h4-7,9,13,16-17,20,22,26,31,33H,2-3,8,10-12,14-15H2,1H3/b7-4+/t20-,22+,26-,27-,28+/m0/s1
• InChI key: InChIKey=XGZZHZMWIXFATA-QHDQMWQDSA-N
• SMILES: CN(C(=O)/C=C/c1ccoc1)[C@H]1CC[C@@]2(O)[C@H]3Cc4ccc(O)c5c4[C@@]2(CCN3CC2CC2)[C@H]1O5