naloxone (CHEBI:7459)

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ChEBI Name	naloxone

ChEBI ID	CHEBI:7459

Definition	A synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an allyl group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C19H21NO4

Net Charge

Average Mass

327.37430

Monoisotopic Mass

327.14706

InChI

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

InChIKey

UZHSEJADLWPNLE-GRGSLBFTSA-N

SMILES

Oc1ccc2C[C@H]3N(CC[C@@]45[C@@H](Oc1c24)C(=O)CC[C@@]35O)CC=C

Roles Classification
Biological Role(s):	mu-opioid receptor antagonist Any compound that exhibits antagonist activity at the mu-opioid receptor metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. (via alkaloid )

Application(s):	mu-opioid receptor antagonist Any compound that exhibits antagonist activity at the mu-opioid receptor central nervous system depressant A loosely defined group of drugs that tend to reduce the activity of the central nervous system. antidote to opioid poisoning A role borne by a molecule that acts to counteract or neutralise the deleterious effects of opioids.

ChEBI Ontology
Outgoing	naloxone (CHEBI:7459) has parent hydride morphinan (CHEBI:35649) naloxone (CHEBI:7459) has role μ-opioid receptor antagonist (CHEBI:50137) naloxone (CHEBI:7459) has role antidote to opioid poisoning (CHEBI:90755) naloxone (CHEBI:7459) has role central nervous system depressant (CHEBI:35488) naloxone (CHEBI:7459) is a morphinane alkaloid (CHEBI:25418) naloxone (CHEBI:7459) is a organic heteropentacyclic compound (CHEBI:38164) naloxone (CHEBI:7459) is a tertiary alcohol (CHEBI:26878) naloxone (CHEBI:7459) is conjugate base of naloxone(1+) (CHEBI:90756)

Incoming	naloxegol (CHEBI:82975) has functional parent naloxone (CHEBI:7459) naloxone(1+) (CHEBI:90756) is conjugate acid of naloxone (CHEBI:7459)

IUPAC Name

3,14-dihydroxy-17-(prop-2-en-1-yl)-4,5α-epoxymorphinan-6-one

Synonyms	Sources
(−)-naloxone	ChEBI
1-N-Allyl-14-hydroxynordihydromorphinone	ChemIDplus
17-allyl-3,14-dihydroxy-4,5α-epoxymorphinan-6-one	ChEBI

Last Modified

22 February 2017