7-Spiroindanyloxymorphone

7-Spiroindanyloxymorphone (SIOM) is a drug that is used in scientific research. It is a selective δ-opioid agonist. It is a derivative of oxymorphone.[1][2][3][4][5]

7-Spiroindanyloxymorphone
Identifiers
IUPAC name
  • (4aR-(4aα,7aα,8α,9cα))-1',3',7,7a,8,9-Hexahydro-3,7a-dihydroxy-12-methylspiro[6H-8,9c](iminoethano)phenanthro[4,5-bcd]furan-6,2'-(2H)inden)-5(4aH)-one
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H25NO4
Molar mass403.478 g·mol−1
3D model (JSmol)
SMILES
  • CN1CCC23[C@@H]4C(=O)C5(CC6=CC=CC=C6C5)C[C@]2([C@@H]1CC7=C3C(=C(C=C7)O)O4)O
InChI
  • InChI=1S/C25H25NO4/c1-26-9-8-24-19-14-6-7-17(27)20(19)30-22(24)21(28)23(13-25(24,29)18(26)10-14)11-15-4-2-3-5-16(15)12-23/h2-7,18,22,27,29H,8-13H2,1H3/t18?,22-,24-,25+/m0/s1 Y
  • Key:YJWDKWRVFJZBCJ-OVKCVFHGSA-N Y
 NY (what is this?)  (verify)

References
  1. Portoghese PS, Moe ST, Takemori AE (August 1993). "A selective delta 1 opioid receptor agonist derived from oxymorphone. Evidence for separate recognition sites for delta 1 opioid receptor agonists and antagonists". Journal of Medicinal Chemistry. 36 (17): 2572–4. doi:10.1021/jm00069a017. PMID 8394935.
  2. Fang X, Larson DL, Portoghese PS (September 1997). "7-spirobenzocyclohexyl derivatives of naltrexone, oxymorphone, and hydromorphone as selective opioid receptor ligands". Journal of Medicinal Chemistry. 40 (19): 3064–70. doi:10.1021/jm970283e. PMID 9301669.
  3. Ohkawa S, DiGiacomo B, Larson DL, Takemori AE, Portoghese PS (May 1997). "7-Spiroindanyl derivatives of naltrexone and oxymorphone as selective ligands for delta opioid receptors". Journal of Medicinal Chemistry. 40 (11): 1720–5. doi:10.1021/jm9700880. PMID 9171881.
  4. Kshirsagar TA, Fang X, Portoghese PS (July 1998). "14-Desoxy analogues of naltrindole and 7-spiroindanyloxymorphone: the role of the 14-hydroxy group at delta opioid receptors". Journal of Medicinal Chemistry. 41 (14): 2657–60. doi:10.1021/jm980209b. PMID 9651172.
  5. Shenderovich MD, Liao S, Qian X, Hruby VJ (June 2000). "A three-dimensional model of the delta-opioid pharmacophore: comparative molecular modeling of peptide and nonpeptide ligands". Biopolymers. 53 (7): 565–80. doi:10.1002/(SICI)1097-0282(200006)53:7<565::AID-BIP4>3.0.CO;2-5. PMID 10766952.
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