CHEBI:53579 - pholcodine

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ChEBI Name pholcodine
ChEBI ID CHEBI:53579
Definition A morphinane alkaloid that is a derivative of morphine with a 2-morpholinoethyl group at the 3-position.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C23H30N2O4
Net Charge 0
Average Mass 398.49530
Monoisotopic Mass 398.221
InChI InChI=1S/C23H30N2O4/c1-24-7-6-23-16-3-4-18(26)22(23)29-21-19(5-2-15(20(21)23)14-17(16)24)28-13-10-25-8-11-27-12-9-25/h2-5,16-18,22,26H,6-14H2,1H3/t16-,17+,18-,22-,23-/m0/s1
InChIKey GPFAJKDEDBRFOS-FKQDBXSBSA-N
SMILES [H][C@@]12Oc3c(OCCN4CCOCC4)ccc4C[C@H]5N(C)CC[C@@]1(c34)[C@@]5([H])C=C[C@@H]2O
Roles Classification
Biological Role(s): opioid analgesic
A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
mu-opioid receptor agonist
A compound that exhibits agonist 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): antitussive
An agent that suppresses cough. Antitussives have a central or a peripheral action on the cough reflex, or a combination of both. Compare with expectorants, which are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing, and mucolytics, which decrease the viscosity of mucus, facilitating its removal by ciliary action and expectoration.
opioid analgesic
A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
mu-opioid receptor agonist
A compound that exhibits agonist activity at the mu-opioid receptor.
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ChEBI Ontology
Outgoing pholcodine (CHEBI:53579) has role μ-opioid receptor agonist (CHEBI:55322)
pholcodine (CHEBI:53579) has role antitussive (CHEBI:51177)
pholcodine (CHEBI:53579) has role opioid analgesic (CHEBI:35482)
pholcodine (CHEBI:53579) is a morphinane alkaloid (CHEBI:25418)
pholcodine (CHEBI:53579) is a organic heteropentacyclic compound (CHEBI:38164)
IUPAC Name
(5α,6α)-17-methyl-3-[2-(morpholin-4-yl)ethoxy]-7,8-didehydro-4,5-epoxymorphinan-6-ol
INNs Sources
folcodina ChemIDplus
pholcodine KEGG DRUG
pholcodinum ChemIDplus
Synonyms Sources
3-(2-(4-Morpholinyl)ethyl)morphine ChemIDplus
3-(2-Morpholinoethyl)morphine NIST Chemistry WebBook
3-morpholinoethylmorphine ChEBI
3-Morpholyläthylmorphin ChemIDplus
7,8-Didehydro-4,5-alpha-epoxy-17-methyl-3-(2-morpholinoethoxy)morphinan-6-alpha-ol ChemIDplus
beta-Morpholinoethylmorphine ChemIDplus
Morpholinylethylmorphine NIST Chemistry WebBook
Tetrahydro-1,4-oxazinylmethylcodeine ChemIDplus
Manual Xrefs Databases
2154 DrugCentral
D07385 KEGG DRUG
Pholcodine Wikipedia
View more database links
Registry Numbers Types Sources
509-67-1 CAS Registry Number ChemIDplus
509-67-1 CAS Registry Number KEGG DRUG
509-67-1 CAS Registry Number NIST Chemistry WebBook
63383 Reaxys Registry Number Reaxys
63383 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
11829134 PubMed citation Europe PMC
12593758 PubMed citation Europe PMC
17667569 PubMed citation Europe PMC
1910552 PubMed citation Europe PMC
19210354 PubMed citation Europe PMC
19563989 PubMed citation Europe PMC
19796197 PubMed citation Europe PMC
22380984 PubMed citation Europe PMC
23283141 PubMed citation Europe PMC
23772895 PubMed citation Europe PMC
29368335 PubMed citation Europe PMC
Last Modified
24 April 2018