NALORPHINE

US Previously Marketed

First approved in 1952

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H21NO3
Molecular Weight	311.3749
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@H]1C=C[C@H]2[C@H]3CC4=C5C(O[C@@H]1[C@@]25CCN3CC=C)=C(O)C=C4

InChI

InChIKey=UIQMVEYFGZJHCZ-SSTWWWIQSA-N

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

HIDE SMILES / InChI

Molecular Formula	C19H21NO3
Molecular Weight	311.3749
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://en.medicine-cure.com/ovr4_nalorfin.htm
Curator's Comment: description was created based on several sources, including: http://en.pharmacodia.com/web/drug/1_12280.html | https://www.ncbi.nlm.nih.gov/pubmed/16433932 | https://www.ncbi.nlm.nih.gov/pubmed/6301606 | doi:10.3181/00379727-77-18904

Nalorphine has a mixed opioid agonist-antagonist properties. Nalorphine inhibits the cholinesterases of mouse brain, bovine erythrocytes and horse serum. It acts on mu-, k- and sigma-opioid receptors. Nalorfin by virtue of the agonistic effect has an analgesic effect but to a much lesser extent than morphine. Initially, before the appearance of a "pure" morphine-naloxone antagonist, nalorphine was used as an antidote for severe respiratory depression and other body function disorders caused by acute poisoning in case of an overdose of morphine, promedol, fentanyl or other narcotic analgesics, or with increased sensitivity to them. At present, nalorphine is practically not used for this purpose. It was replaced by naloxone. Large doses of nalorphine can cause nausea, cramps, drowsiness, headache, mental stimulation.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Acetylcholinesterase 209 Target ID: CHEMBL3198 Sources: doi: 10.3181/00379727-77-18904	Inhibitor 8504
Kappa opioid receptor 115 Target ID: CHEMBL4329 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16433932	Agonist 2752	1.6 nM [Ki]
Mu opioid receptor 231 Target ID: CHEMBL270 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8819494	Partial Agonist 297
Sigma opioid receptor 64 Target ID: CHEMBL3602 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6301606	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Opioid overdose 2 Sources: http://en.medicine-cure.com/ovr4_nalorfin.htm	Secondary		Approved 8583	Norfin Approved Use It is used as an antidote for opiates.

C_max

Value	Dose	Co-administered	Analyte	Population
1.12 μg/g REVIEW https://www.springer.com/gp/book/9781468418712	2 mg/kg single, subcutaneous dose: 2 mg/kg route of administration: Subcutaneous experiment type: SINGLE co-administered:		NALORPHINE brain	Canis lupus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
1.17 μg × h/g REVIEW https://www.springer.com/gp/book/9781468418712	2 mg/kg single, subcutaneous dose: 2 mg/kg route of administration: Subcutaneous experiment type: SINGLE co-administered:		NALORPHINE brain	Canis lupus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
23 min REVIEW https://www.springer.com/gp/book/9781468418712	2 mg/kg single, subcutaneous dose: 2 mg/kg route of administration: Subcutaneous experiment type: SINGLE co-administered:		NALORPHINE brain	Canis lupus population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	SULT1A1 37 SULT1A3 31 SULT1E1 22 SULT2A1 28 UGT2B1 14

Drug as victim

Target	Modality	Activity
SULT1A1 37	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4459640/	major
SULT1E1 22	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4459640/	not detected
SULT1A3 31	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4459640/	yes
SULT2A1 28	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4459640/	yes
UGT2B1 14	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9029056/	yes

Sourcing

Vendor/Aggregator	ID	URL
Alsachim	3976	http://www.alsachim.com/product-C5281-glo.bal-view.html
Chemieliva Pharmaceutical Co., Ltd	PBCM1361788
ChemMol	99117845	http://www.chemmol.com/chemmol/99117845.html
Compound Cloud	5284595
Compound Cloud	5484366
eMolecules	260189857
NovoSeek	5284595
Sigma Aldrich	1452002
Sigma Aldrich	1452002\|USP
Sigma Aldrich	N-924
Sigma Aldrich	N0762
Sigma Aldrich	N0762\|SIGMA
Toronto Research Chemicals	KIT6360
Toronto Research Chemicals	N284450
ZINC	ZINC000003875420	http://zinc15.docking.org/substances/ZINC000003875420

PubMed

Title	Date	PubMed
Opioid antagonists differ according to negative intrinsic efficacy in a mouse model of acute dependence.	2005-08	15912139
Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications.	1998-03	9686407
Activation of the cloned human kappa opioid receptor by agonists enhances [35S]GTPgammaS binding to membranes: determination of potencies and efficacies of ligands.	1997-08	9262330
Changes in nalorphine-induced hyperprolactinaemia after bromocriptine or sulpiride administration.	1982	7106173

Patents

Sample Use Guides

In Vivo Use Guide

Adults appoint 0,005 - 0,01 g (1 - 2 ml of a 0.5% solution). If the effect is insufficient, the injections are repeated at intervals of 10 to 15 minutes. The total dose should not exceed 0.04 g (8 ml of 0.5% solution).

Route of Administration: Other

In Vitro Use Guide

Maximum stimulation of [35S]GTPyS binding by Nalorphine using a single saturating concentration of ligand (10 uM) was compared with stimulation by DAAMGO (10 uM). Intrinsic activity determined for Nalorphine in C6 glioma cells was 9%.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:35:45 GMT 2025` Edited by `admin` on `Mon Mar 31 17:35:45 GMT 2025`
Record UNII	U59WB2WRY2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NALORPHINE SERB

Preferred Name

English

NALORPHINE

Official Name

English

nalorphine [INN]

Common Name

English

NALORPHINE [MART.]

Common Name

English

Nalorphine [WHO-DD]

Common Name

English

MORPHINAN-3,6-DIOL, 7,8-DIDEHYDRO-4,5-EPOXY-17-(2-PROPENYL)-(5.ALPHA.,6.ALPHA.)-

Systematic Name

English

NALORPHINE [MI]

Common Name

English

NALORPHINE [HSDB]

Common Name

English

Classification Tree Code System Code

DEA NO.

9400