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.:232 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.:232,237