Cyclorphan
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Systematic (IUPAC) name | |
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(−)-3-Hydroxy-N-cyclopropylmethylmorphinan
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Identifiers | |
CAS Number | 4163-15-9 |
PubChem | CID 5359966 |
ChemSpider | 4514407 |
ChEMBL | CHEMBL49269 |
Chemical data | |
Formula | C20H27NO |
Molar mass | 297.434 g/mol |
3D model (Jmol) | Interactive image |
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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]
- ^ 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
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MOR |
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DOR |
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KOR |
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NOP |
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Unsorted | |
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See also: Peptide receptor modulators
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