Cyclorphan
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IUPAC name
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| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.021.825  |
| Chemical and physical data | |
| Formula | C20H27NO |
| Molar mass | 297.442 g·mol−1 |
| 3D model (JSmol) | |
| Density | 1.19 g/cm3 |
| Melting point | 188 °C (370 °F) |
| Boiling point | 458.4 °C (857.1 °F) |
SMILES
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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
References
- 1 2 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
- 1 2 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
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