Chemistry:Nalorphine
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| Trade names | Lethidrone, Nalline |
| Other names | N-Allylnormorphine |
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| Formula | C19H21NO3 |
| Molar mass | 311.381 g·mol−1 |
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Nalorphine (INN) (brand names Lethidrone, Nalline), also known as N-allylnormorphine, is a mixed opioid agonist–antagonist with opioid antagonist and analgesic properties.[1] It was introduced in 1954[2] and was used as an antidote to reverse opioid overdose and in a challenge test to determine opioid dependence.[3]
Nalorphine was the second opioid antagonist to be introduced, preceded by nalodeine (N-allylnorcodeine) in 1915 and followed by naloxone in 1960 and naltrexone in 1963.[2] Due to potent activation of the κ-opioid receptor, nalorphine produces side effects such as dysphoria, anxiety, confusion, and hallucinations, and for this reason, is no longer used medically.[1][2][4]
Pharmacology
Pharmacodynamics
Nalorphine acts at two opioid receptors — the μ-opioid receptor (MOR) where it has antagonistic effects, and at the κ-opioid receptor (KOR) (Ki = 1.6 nM; EC50 = 483 nM; Emax = 95%) where it exerts high-efficacy partial agonist/near-full agonist characteristics.[5]
Chemistry
Analogues
Nalorphine has a number of analogues including niconalorphine (the nicomorphine analogue), diacetylnalorphine (heroin analogue), dihydronalorphine (dihydromorphine), and a number of others as well as a number of codeine-based analogues.[6]
Synthesis
More recently, it has become much more commonplace to use ethyl chloroformate instead of cyanogen bromide for the Von Braun degradation demethylation step. See for example the list of phenyltropanes or the synthesis of paroxetine for further examples of this.
See also
References
- ↑ 1.0 1.1 The Dependence Phenomenon. Springer Science & Business Media. 6 December 2012. pp. 121–. ISBN 978-94-011-7457-2. https://books.google.com/books?id=rN7dBgAAQBAJ&pg=PT121.
- ↑ 2.0 2.1 2.2 Aggrawal, Anil. APC Essentials of Forensic Medicine and Toxicology. Avichal Publishing Company. pp. 554–. ISBN 978-81-7739-441-2. https://books.google.com/books?id=iSH8CgAAQBAJ&pg=PA554.
- ↑ "Medicine: Drug Detector". Time (magazine). 24 December 1956. http://www.time.com/time/magazine/article/0,9171,808859,00.html.
- ↑ Pharmacology and Pharmacotherapeutics. Elsevier Health Sciences APAC. 27 July 2015. pp. 166–. ISBN 978-81-312-4371-8. https://books.google.com/books?id=h2drCgAAQBAJ&pg=PA166.
- ↑ "Pharmacological profiles of opioid ligands at kappa opioid receptors". BMC Pharmacology 6 (1): 3. January 2006. doi:10.1186/1471-2210-6-3. PMID 16433932.
- ↑ Opioid Analgesics: Chemistry and Receptors. Springer Science & Business Media. 29 June 2013. ISBN 9781489905857. https://books.google.com/books?id=vwAHCAAAQBAJ&q=dihydronalorphine&pg=PA507.
- ↑ "The preparation of N-allylnormorphine.". Journal of the American Chemical Society 63 (1): 314. January 1941. doi:10.1021/ja01846a504.
- ↑ "N-Allylnormorphine". Journal of the American Chemical Society 64 (4): 869–870. 1942. doi:10.1021/ja01256a036.
- ↑ "The pharmacology of N-allylnormorphine as compared with morphine.". Journal of Pharmacology and Experimental Therapeutics 82 (3): 339–48. November 1944. http://jpet.aspetjournals.org/content/82/3/339.short.
- ↑ U.S. Patent 2,364,833 (1944); Weijlard, U.S. Patent 2,891,954 (1959 to Merck & Co.).
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