Nalorphine

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Chemical compound

title: "Nalorphine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["abandoned-drugs", "allylamines", "antidotes", "cyclohexenes", "4,5-epoxymorphinans", "hallucinogenic-kappa-opioid-receptor-agonists", "hydroxyarenes", "mu-opioid-receptor-antagonists", "secondary-alcohols", "semisynthetic-opioids"] description: "Chemical compound" topic_path: "arts/music" source: "https://en.wikipedia.org/wiki/Nalorphine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Verifiedfields = verified | Watchedfields = verified | verifiedrevid = 402503832 | IUPAC_name = 17-allyl-7,8-didehydro-4,5α-epoxymorphinan-3,6α-diol | image = Nalorphine.svg | image_class = skin-invert-image | width = 225px

| tradename = Lethidrone, Nalline | Drugs.com = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = S4 | legal_BR = A2 | legal_BR_comment = | legal_CA = Schedule I | legal_UK = | legal_US = Schedule III | legal_status = | routes_of_administration =

| bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =

| CAS_number_Ref = | CAS_number = 62-67-9 | ATC_prefix = V03 | ATC_suffix = AB02 | PubChem = 5284595 | IUPHAR_ligand = 1629 | DrugBank_Ref = | DrugBank = DB11490 | ChemSpiderID_Ref = | ChemSpiderID = 4447643 | UNII_Ref = | UNII = U59WB2WRY2 | ChEBI_Ref = | ChEBI = 7458 | ChEMBL_Ref = | ChEMBL = 415284 | KEGG_Ref = | KEGG = D08247 | synonyms = N-Allylnormorphine

| C=19 | H=21 | N=1 | O=3 | SMILES = O[C@@H]1[C@@H]2OC3=C4C(C[C@H]5N(CC[C@]42[C@@]5([H])C=C1)CC=C)=CC=C3O | StdInChI_Ref = | StdInChI = 1S/C19H21NO3/c1-2-8-20-9-7-19-12-4-6-15(22)18(19)23-17-14(21)5-3-11(16(17)19)10-13(12)20/h2-6,12-13,15,18,21-22H,1,7-10H2/t12-,13+,15-,18-,19-/m0/s1 | StdInChIKey_Ref = | StdInChIKey = UIQMVEYFGZJHCZ-SSTWWWIQSA-N

Nalorphine (; also known as N-allylnormorphine; brand names Lethidrone and Nalline) is a mixed opioid agonist–antagonist with opioid antagonist and analgesic properties. It was introduced in 1954 and was used as an antidote to reverse opioid overdose and in a challenge test to determine opioid dependence.

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. 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.

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.

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.

Synthesis

::figure[src="https://upload.wikimedia.org/wikipedia/commons/a/a2/Nalorphine_synthesis.png" caption="2891954}} (1959 to [[Merck & Co.]]).]]{{clear-left}}"] ::

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.

References

References

  1. Anvisa. (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial". [[Diário Oficial da União]].
  2. (6 December 2012). "The Dependence Phenomenon". Springer Science & Business Media.
  3. Aggrawal, Anil. "APC Essentials of Forensic Medicine and Toxicology". Avichal Publishing Company.
  4. (24 December 1956). "Medicine: Drug Detector".
  5. (27 July 2015). "Pharmacology and Pharmacotherapeutics". Elsevier Health Sciences APAC.
  6. (January 2006). "Pharmacological profiles of opioid ligands at kappa opioid receptors". BMC Pharmacology.
  7. (29 June 2013). "Opioid Analgesics: Chemistry and Receptors". Springer Science & Business Media.
  8. (January 1941). "The preparation of N-allylnormorphine.". Journal of the American Chemical Society.
  9. (1942). "N-Allylnormorphine". Journal of the American Chemical Society.
  10. (November 1944). "The pharmacology of N-allylnormorphine as compared with morphine.". Journal of Pharmacology and Experimental Therapeutics.
  11. {{US patent. 2364833 (1944); Weijlard, {{US patent. 2891954 (1959 to [[Merck & Co.]]).

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abandoned-drugsallylaminesantidotescyclohexenes4,5-epoxymorphinanshallucinogenic-kappa-opioid-receptor-agonistshydroxyarenesmu-opioid-receptor-antagonistssecondary-alcoholssemisynthetic-opioids