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
Molar mass 297.434 g/mol
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 analgesic of the morphinan family that was never marketed.[1] 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).[2][3] The drug was first synthesized in 1964 by scientists at Research Corporation.[4][5]: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.[1][5]:232, 237

See also[edit]

References[edit]

  1. ^ a b Maxwell Gordon (2 December 2012). Psychopharmacological Agents. Elsevier Science. pp. 19–. ISBN 978-0-323-15963-0. 
  2. ^ Linda P. Dwoskin (29 January 2014). Emerging Targets & Therapeutics in the Treatment of Psychostimulant Abuse. Elsevier Science. pp. 403–. ISBN 978-0-12-420177-4. 
  3. ^ Aldrich JV, Vigil-Cruz SC (2003). "Narcotic Analgesics". Burger's Medicinal Chemistry and Drug Discovery (7th ed.). pp. 331–482. doi:10.1002/0471266949.bmc100. ISBN 9780471266945. 
  4. ^ US Patent 3,285,922
  5. ^ a b 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