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Chemical compound
Nalorphine
Trade names Lethidrone, Nalline Other names N -Allylnormorphine
AHFS /
Drugs.com
International Drug Names
ATC code
Legal status
17-allyl-7,8-didehydro-4,5α-epoxymorphinan-3,6α-diol
CAS Number
PubChem
CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (
EPA )
ECHA InfoCard
100.000.497
Formula C 19 H 21 N O 3
Molar mass 311.381 g·mol−1 3D model (
JSmol )
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=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
(verify)
Nalorphine (
INN Tooltip 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]
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.
[6]
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.
[7]
Synthesis
Nalorphine synthesis:
[8] amended procedure:
[9]
[10]
[11]
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
^
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 .
^ Gharagozlou P, Hashemi E, DeLorey TM, Clark JD, Lameh J (January 2006).
"Pharmacological profiles of opioid ligands at kappa opioid receptors" . BMC Pharmacology . 6 (1): 3.
doi :
10.1186/1471-2210-6-3 .
PMC
1403760 .
PMID
16433932 .
^ Casy AF, Parfitt RT (29 June 2013).
Opioid Analgesics: Chemistry and Receptors . Springer Science & Business Media.
ISBN
9781489905857 – via Google Books.
^ McCawley EL, Hart ER, Marsh DF (January 1941). "The preparation of N-allylnormorphine". Journal of the American Chemical Society . 63 (1): 314.
doi :
10.1021/ja01846a504 .
^ Weijlard J, Erickson AE (1942). "N-Allylnormorphine". Journal of the American Chemical Society . 64 (4): 869–870.
doi :
10.1021/ja01256a036 .
^ Hart ER, McCawley EL (November 1944).
"The pharmacology of N-allylnormorphine as compared with morphine" . Journal of Pharmacology and Experimental Therapeutics . 82 (3): 339–48.
^
U.S. patent 2,364,833 (1944); Weijlard,
U.S. patent 2,891,954 (1959 to
Merck & Co. ).
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