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| Trade names | Lethidrone, Nalline |
| Other names | N-Allylnormorphine |
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| ECHA InfoCard | 100.000.497 |
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| Formula | C19H21NO3 |
| Molar mass | 311.381 g·mol−1 |
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Nalorphine (INNTooltip International Nonproprietary Name; also known asN-allylnormorphine; brand namesLethidrone andNalline) is a mixedopioidagonist–antagonist withopioid antagonist andanalgesic properties.[2] It was introduced in 1954[3] and was used as anantidote to reverseopioid overdose and in a challenge test to determineopioid dependence.[4]
Nalorphine was the second opioid antagonist to be introduced, preceded bynalodeine (N-allylnorcodeine) in 1915 and followed bynaloxone in 1960 andnaltrexone in 1963.[3] Due to potent activation of theκ-opioid receptor, nalorphine producesside effects such asdysphoria,anxiety,confusion, andhallucinations, and for this reason, is no longer used medically.[2][3][5]
Nalorphine acts at twoopioid receptors — theμ-opioid receptor (MOR) where it hasantagonistic effects, and at theκ-opioid receptor (KOR) (Ki = 1.6 nM;EC50 = 483 nM;Emax = 95%) where it exerts high-efficacypartial agonist/near-full agonist characteristics.[6]
Nalorphine has a number ofanalogues includingniconalorphine (thenicomorphine analogue),diacetylnalorphine (heroin analogue),dihydronalorphine (dihydromorphine), and a number of others as well as a number ofcodeine-based analogues.[7]
More recently, it has become much more commonplace to useethyl chloroformate instead ofcyanogen bromide for theVon Braun degradation demethylation step. See for example thelist of phenyltropanes or the synthesis ofparoxetine for further examples of this.
