Cyclorphan

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Cyclorphan
Cyclorphan structure.svg
Systematic (IUPAC) name
(−)-3-Hydroxy-N-cyclopropylmethylmorphinan
Identifiers
CAS Number 4163-15-9
PubChem CID: 5359966
ChemSpider 4514407
ChEMBL CHEMBL49269
Chemical data
Formula C20H27NO
Molecular mass 297.434 g/mol
  • Oc1ccc4c(c1)[C@@]25[C@H]([C@H](N(CC2)CC3CC3)C4)CCCC5
Physical data
Density 1.19 g/cm3
Melting point 188 °C (370 °F)
Boiling point 458.4 °C (857.1 °F)

Cyclorphan is an opioid compound that is a δ-opioid receptor agonist, a κ-opioid receptor agonist, and a μ-opioid receptor antagonist.[1] Chemically, it is a morphinan and is related to levorphanol.[1]

It was first synthesized in 1964 by scientists at Research Corporation.[2][3]:232 In clinical trials, it had relatively long duration, good absorption, and provided strong pain relief but caused symptoms of psychosis, so its development was not continued.[3]:232, 237

References

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  1. ↑ 1.0 1.1 Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ US Patent 3,285,922
  3. ↑ 3.0 3.1 Varghese V & Hudlicky T. A Short History of the Discovery and Development of Naltrexone and Other Morphine Derivatives. Chapter 6 in Natural Products in Medicinal Chemistry, Volume 60 of Methods and Principles in Medicinal Chemistry. Ed. Stephen Hanessian. John Wiley & Sons, 2013. ISBN 9783527676552
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