Cyclorphan

Cyclorphan
Identifiers
  • (−)-3-Hydroxy-N-cyclopropylmethylmorphinan
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.021.825
Chemical and physical data
FormulaC20H27NO
Molar mass297.442 g·mol−1
3D model (JSmol)
Density1.19 g/cm3
Melting point188 °C (370 °F)
Boiling point458.4 °C (857.1 °F)
  • Oc1ccc4c(c1)[C@@]25[C@H]([C@H](N(CC2)CC3CC3)C4)CCCC5

Cyclorphan is an opioid analgesic of the morphinan family that was never marketed. It acts as a μ-opioid receptor (MOR) weak partial agonist or antagonist, κ-opioid receptor (KOR) full agonist, and, to a much lesser extent, δ-opioid receptor (DOR) agonist (75-fold lower affinity relative to the KOR). The drug was first synthesized in 1964 by scientists at Research Corporation. In clinical trials, it had relatively long duration, good absorption, and provided strong pain relief but produced psychotomimetic effects via KOR activation, so its development was not continued.