Nalorphine

Nalorphine
Clinical data

AHFS/Drugs.com	International Drug Names
ATC code	V03AB02 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: Schedule I
Identifiers
IUPAC name (5α,6α)-17-allyl- 7,8-didehydro- 4,5-epoxymorphinan- 3,6-diol
Synonyms	(−)−(5R,6S)-9α-allyl- 4,5-epoxymorphin- 7-en- 3,6-diol
CAS Number	62-67-9^Y
PubChem (CID)	5284595
IUPHAR/BPS	1629
ChemSpider	4447643^Y
UNII	U59WB2WRY2^N
ChEMBL	CHEMBL415284^N
ECHA InfoCard	100.000.497
Chemical and physical data
Formula	C₁₉H₂₁NO₃
Molar mass	311.375 g/mol
3D model (Jmol)	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^Y Key:UIQMVEYFGZJHCZ-SSTWWWIQSA-N^Y
^NY (what is this?)

Nalorphine (INN) (brand names Lethidrone, Nalline), also known as N-allyl-normorphine, 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. It acts at two opioid receptors — the μ-opioid receptor (MOR) where it has antagonistic effects, and at the κ-opioid receptor (KOR) (K_i = 1.6 nM; EC₅₀ = 483 nM; E_max = 95%) where it exerts high-efficacy partial agonist/near-full agonist characteristics. 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 KOR, nalorphine produces side effects such as dysphoria, anxiety, confusion, and hallucinations, and for this reason, is no longer used medically.

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.