Cyclorphan

Cyclorphan
Identifiers
	IUPAC name (−)-3-Hydroxy-N-cyclopropylmethylmorphinan;
CAS Number	4163-15-9;
PubChem CID	5359966;
ChemSpider	4514407;
UNII	U6Z73N36V0;
ChEMBL	ChEMBL49269;
CompTox Dashboard (EPA)	DTXSID50878519 ;
ECHA InfoCard	100.021.825
Chemical and physical data
Formula	C20H27NO
Molar mass	297.442 g·mol−1
3D model (JSmol)	Interactive image;
Density	1.19 g/cm3
Melting point	188 °C (370 °F)
Boiling point	458.4 °C (857.1 °F)
	SMILES 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.^[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}

References

^ ^a ^b Maxwell Gordon (2 December 2012). Psychopharmacological Agents. Elsevier Science. pp. 19–. ISBN 978-0-323-15963-0.
^ 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.
^ 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.
^ US Patent 3,285,922
^ ^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

This analgesic-related article is a stub. You can help Wikipedia by expanding it.