Naloxone (CED0001584)

Record Information

Version

1.0

Creation Date

2016-05-22 03:43:58 UTC

Update Date

2026-05-14 16:58:33 UTC

Accession Number

CHEM016797

Identification

Common Name

Naloxone

Class

Small Molecule

Description

Naloxone belongs to the phenanthrenes and derivatives, a class of benzenoids within the organic compounds. It has the chemical formula C19H21NO4 and an average molecular weight of 327.37 g/mol. Biologically, the compound serves as an antidote (PMC3795186). Its protein targets include six recorded proteins, acting as an antagonist, binder, or inhibitor of the Mu-type opioid receptor (OPRM1), Estrogen receptor (ESR1), Delta-type opioid receptor (OPRD1), Kappa-type opioid receptor (OPRK1), and two other proteins. The compound is found in or released from seven recorded sources. These include pharmaceuticals, veterinary products, and healthcare items such as analgesics, drugs for constipation, and unclassified therapeutic products. It is also associated with electrical and electronic equipment, specifically antennas and amplifiers, as well as household cleaning and consumer products, including other smoking requisites and non-electric simulated smoking devices. Recorded exposure routes for naloxone include buccal, intramuscular, intravenous, nasal, oral, parenteral, subcutaneous, sublingual, and topical administration. Additionally, the compound is used in plastics, specifically in Polyamide, Low-Density Polyethylene, and High-Density Polyethylene.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-Naloxone	ChEBI
1-N-Allyl-14-hydroxynordihydromorphinone	ChEBI
17-Allyl-3,14-dihydroxy-4,5alpha-epoxymorphinan-6-one	ChEBI
Naloxona	ChEBI
Naloxonum	ChEBI
DBL Naloxone	Kegg
17-Allyl-3,14-dihydroxy-4,5a-epoxymorphinan-6-one	Generator
17-Allyl-3,14-dihydroxy-4,5α-epoxymorphinan-6-one	Generator
EN 1530 base	HMDB
L-Naloxone	HMDB
N-Allylnoroxymorphone	HMDB
Nalossone	HMDB
Abello brand OF naloxone hydrochloride	HMDB
Abello, naloxone	HMDB
Boots brand OF naloxone hydrochloride	HMDB
Bristol-myers squibb brand OF naloxone hydrochloride	HMDB
Curamed brand OF naloxone hydrochloride	HMDB
endo Brand OF naloxone hydrochloride	HMDB
Narcanti	HMDB
Ratiopharm brand OF naloxone hydrochloride	HMDB
Dihydride, naloxone hydrochloride	HMDB
Naloxon ratiopharm	HMDB
Naloxone hydrochloride	HMDB
Naloxone hydrochloride, (5 beta,9 alpha,13 alpha,14 alpha)-isomer	HMDB
SERB brand OF naloxone hydrochloride	HMDB
Bristol myers squibb brand OF naloxone hydrochloride	HMDB
Curamed, naloxon	HMDB
Lamepro brand OF naloxone hydrochloride	HMDB
MRZ 2593BR	HMDB
Nalone	HMDB
Naloxon-ratiopharm	HMDB
Hydrobromide, naloxone	HMDB
Hydrochloride dihydride, naloxone	HMDB
Hydrochloride, naloxone	HMDB
MRZ 2593 BR	HMDB
MRZ 2593-BR	HMDB
Naloxon curamed	HMDB
Naloxone abello	HMDB
Naloxone hydrochloride dihydride	HMDB
Naloxone, (5 beta,9 alpha,13 alpha,14 alpha)-isomer	HMDB
Naloxonratiopharm	HMDB
Naloxone hydrobromide	HMDB
Narcan	HMDB
United drug brand OF naloxone hydrochloride	HMDB

Chemical Formula

C₁₉H₂₁NO₄

Average Molecular Mass

327.374 g/mol

Monoisotopic Mass

327.147 g/mol

CAS Registry Number

465-65-6

IUPAC Name

(1S,5R,13R,17S)-10,17-dihydroxy-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-one

Traditional Name

naloxone

SMILES

[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(CC=C)[C@]([H])(C4)[C@]1(O)CCC2=O

InChI Identifier

InChI=1S/C19H21NO4/c1-2-8-20-9-7-18-15-11-3-4-12(21)16(15)24-17(18)13(22)5-6-19(18,23)14(20)10-11/h2-4,14,17,21,23H,1,5-10H2/t14-,17+,18+,19-/m1/s1

InChI Key

UZHSEJADLWPNLE-GRGSLBFTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Not Available

Direct Parent

Phenanthrenes and derivatives

Alternative Parents

Substituents

Phenanthrene
Isoquinolone
Tetralin
Coumaran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Aralkylamine
Piperidine
Cyclic alcohol
Tertiary alcohol
1,2-aminoalcohol
Ketone
Tertiary aliphatic amine
Tertiary amine
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Organooxygen compound
Alcohol
Organic oxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

morphinane alkaloid (CHEBI:7459 )
organic heteropentacyclic compound (CHEBI:7459 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

antidote

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	5.64 g/L	ALOGPS
logP	1.47	ALOGPS
logP	1.62	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	7.27	ChemAxon
pKa (Strongest Basic)	10.63	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	70 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	88.72 m³·mol⁻¹	ChemAxon
Polarizability	33.8 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0a6r-9042000000-3da4b2172456d62748f0	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-004i-9703600000-474943cf0224b80b9bab	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0900000000-6b7de93b51a79132630f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0139000000-e70921e0765c3389ce85	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-0790000000-385321bfef7553f8994a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-0009000000-2b2b5b609cf6e1a1d0a7	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-0019000000-fdc81a17ea0adfa1d6b1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03fr-0009000000-1e89424c27afc0579ffc	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03dl-5079000000-7ad11d1224dead9d51b5	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9030000000-102851f487961aeb63cb	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0009000000-8c2763e72d5fce389611	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-056r-0049000000-d9a6f9d54d49fda8a151	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00ku-2090000000-fbfe8d648c7bfc3bbe9f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0009000000-354160c39518aa1987e3	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03fr-0019000000-c4826be6e2657469ccea	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00b9-0096000000-16546df9ae1b2c3cee96	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0009000000-82e8b7e0c70cdc0f9fe6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0009000000-ad63c6111240451f0f01	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00b9-0049000000-d10f137bf09021c8d430	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
700.0	Log mg/kg	[390:1200]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
253	Drugs for constipation	Healthcare, pharmaceuticals & veterinary products	Not Available
370	Analgesics	Healthcare, pharmaceuticals & veterinary products	Not Available
409	Unclassified therapeutic products	Healthcare, pharmaceuticals & veterinary products	Not Available
505	Amplifiers	Electrical & Electronic Equipment	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
560	Other Smoking Requisites	Household cleaning & consumer products	Not Available

Pathways

3 pathways

Naloxone Action Pathway

Naloxone Opioid Antagonist Action Pathway

Naloxone Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Predicted (SEA)	1.55698
Click to view 3D structure	Mu-type opioid receptor	P33535	Rattus norvegicus	Predicted (SEA)	2.95827
Click to view 3D structure	Delta-type opioid receptor	P33533	Rattus norvegicus	Predicted (SEA)	1.55698
Click to view 3D structure	Kappa-type opioid receptor	P41145	Humans	Predicted (SEA)	3.42537
Click to view 3D structure	Kappa-type opioid receptor	P41144	Cavia porcellus	Predicted (SEA)	2.17978
Click to view 3D structure	Mu-type opioid receptor	P42866	Mus musculus	Predicted (SEA)	0.467095
Click to view 3D structure	Mu-type opioid receptor	P97266	Cavia porcellus	Predicted (SEA)	3.26967
Click to view 3D structure	Delta-type opioid receptor	P32300	Mus musculus	Predicted (SEA)	3.26967
Click to view 3D structure	Delta-type opioid receptor	P41143	Humans	Predicted (SEA)	3.89246
Click to view 3D structure	Kappa-type opioid receptor	P34975	Rattus norvegicus	Predicted (SEA)	1.32344
Click to view 3D structure	Kappa-type opioid receptor	P33534	Mus musculus	Predicted (SEA)	0.778492
Click to view 3D structure	Mu-type opioid receptor	P79350	Bos taurus	Predicted (SEA)	0.0778492
Click to view 3D structure	Nociceptin receptor	P41146	Humans	Predicted (SEA)	28.6485
Click to view 3D structure	Cytochrome P450 2D6	P10635	Humans	Predicted (SEA)	48.1887
Click to view 3D structure	Voltage-gated inwardly rectifying potassium channel KCNH2	Q12809	Humans	Predicted (SEA)	120.822
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	83.7658
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q9R0C9	Rattus norvegicus	Predicted (SEA)	22.6541
Click to view 3D structure	Orexin/Hypocretin receptor type 1	O43613	Humans	Predicted (SEA)	19.3845
Click to view 3D structure	C-C chemokine receptor type 5	P51682	Mus musculus	Predicted (SEA)	1.86838
Click to view 3D structure	NADPH oxidase 2	P04839	Humans	Predicted (SEA)	0.389246
Click to view 3D structure	C-C chemokine receptor type 5	P51681	Humans	Predicted (SEA)	59.3211
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	O55242	Mus musculus	Predicted (SEA)	18.9952
Click to view 3D structure	G_PROTEIN_RECEP_F1_2 domain-containing protein	F7HEV7	Macaca mulatta	Predicted (SEA)	9.41976
Click to view 3D structure	Kappa-type opioid receptor	H9FL65	Macaca mulatta	Predicted (SEA)	9.41976
Click to view 3D structure	D(2) dopamine receptor	P61169	Rat	Predicted (SEA)	849.179