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7-Spiroindanyloxymorphone

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Chemical compound

Pharmaceutical compound

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	150380-34-0^N
PubChemCID	5487084
ChemSpider	8176808^Y
UNII	35UF85T692
CompTox Dashboard(EPA)	DTXSID60933926
Chemical and physical data
Formula	C₂₅H₂₅NO₄
Molar mass	403.478 g·mol⁻¹
3D model (JSmol)	Interactive image
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)

7-Spiroindanyloxymorphone (SIOM) is a drug that is used in scientific research. It is a selectiveδ-opioid agonist. It is a derivative ofoxymorphone.^[1]^[2]^[3]^[4]^[5]

References

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^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.
^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.
^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.
^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.
^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.