Nalorphine

Nalorphine
Clinical data
Trade names	Lethidrone, Nalline
Other names	N-Allylnormorphine
AHFS/Drugs.com	International Drug Names
ATC code	V03AB02 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class A2 (Narcotic drugs); CA: Schedule I; US: Schedule III;
Identifiers
	IUPAC name 17-allyl-7,8-didehydro-4,5α-epoxymorphinan-3,6α-diol;
CAS Number	62-67-9 ;
PubChem CID	5284595;
IUPHAR/BPS	1629;
DrugBank	DB11490 ;
ChemSpider	4447643 ;
UNII	U59WB2WRY2;
KEGG	D08247;
ChEBI	CHEBI:7458;
ChEMBL	ChEMBL415284 ;
CompTox Dashboard (EPA)	DTXSID3023348 ;
ECHA InfoCard	100.000.497
Chemical and physical data
Formula	C19H21NO3
Molar mass	311.381 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O[C@H]2\C=C/[C@H]5[C@@H]4N(CC[C@@]51c3c(O[C@H]12)c(O)ccc3C4)C\C=C;
	InChI InChI=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 ; Key:UIQMVEYFGZJHCZ-SSTWWWIQSA-N ;
	(verify)

Nalorphine (INNTooltip International Nonproprietary Name) (brand names Lethidrone, Nalline), also known as N-allylnormorphine, is a mixed opioid agonist–antagonist with opioid antagonist and analgesic properties.^[2] It was introduced in 1954^[3] and was used as an antidote to reverse opioid overdose and in a challenge test to determine opioid dependence.^[4]

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.^[3] 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.^[2]^[3]^[5]

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-03.
^ ^a ^b Glatt M (6 December 2012). The Dependence Phenomenon. Springer Science & Business Media. pp. 121–. ISBN 978-94-011-7457-2.
^ ^a ^b ^c Aggrawal A. APC Essentials of Forensic Medicine and Toxicology. Avichal Publishing Company. pp. 554–. ISBN 978-81-7739-441-2.
^ "Medicine: Drug Detector". Time. 24 December 1956. Archived from the original on July 26, 2005.
^ Satoskar RS, Rege N, Bhandarkar SD (27 July 2015). Pharmacology and Pharmacotherapeutics. Elsevier Health Sciences APAC. pp. 166–. ISBN 978-81-312-4371-8.