Cyclorphan

Cyclorphan

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
SMILES Oc1ccc4c(c1)[C@@]25[C@H]([C@H](N(CC2)CC3CC3)C4)CCCC5
Physical data
Density	1.19 g/cm^3
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

• Butorphanol
• Levomethorphan
• Levorphanol
• Nalbuphine
• Oxilorphan
• Proxorphan
• Xorphanol

References

1. 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.). p. 331-482. doi:10.1002/0471266949.bmc100. ISBN 9780471266945.
4. US Patent 3,285,922
5. 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