CHEBI:3242 - butorphanol

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ChEBI Name butorphanol
ChEBI ID CHEBI:3242
Definition Levorphanol in which a hydrogen at position 14 of the morphinan skeleton is substituted by hydroxy and one of the hydrogens of the N-methyl group is substituted by cyclopropyl. A semi-synthetic opioid agonist-antagonist analgesic, it is used as its (S,S)-tartaric acid salt for relief or moderate to severe pain.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:145838
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Formula C21H29NO2
Net Charge 0
Average Mass 327.46050
Monoisotopic Mass 327.220
InChI InChI=1S/C21H29NO2/c23-17-7-6-16-12-19-21(24)9-2-1-8-20(21,18(16)13-17)10-11-22(19)14-15-4-3-5-15/h6-7,13,15,19,23-24H,1-5,8-12,14H2/t19-,20+,21-/m1/s1
InChIKey IFKLAQQSCNILHL-QHAWAJNXSA-N
SMILES Oc1ccc2C[C@H]3N(CC[C@@]4(CCCC[C@@]34O)c2c1)CC1CCC1
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.
kappa-opioid receptor agonist
A compound that exhibits agonist activity at the kappa-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.
kappa-opioid receptor agonist
A compound that exhibits agonist activity at the kappa-opioid receptor.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing butorphanol (CHEBI:3242) has role κ-opioid receptor agonist (CHEBI:59282)
butorphanol (CHEBI:3242) has role μ-opioid receptor agonist (CHEBI:55322)
butorphanol (CHEBI:3242) has role antitussive (CHEBI:51177)
butorphanol (CHEBI:3242) has role opioid analgesic (CHEBI:35482)
butorphanol (CHEBI:3242) is a morphinane alkaloid (CHEBI:25418)
Incoming butorphanol D-tartrate (CHEBI:3243) has part butorphanol (CHEBI:3242)
IUPAC Name
17-(cyclobutylmethyl)morphinan-3,14-diol
INNs Sources
butorfanol ChemIDplus
butorphanol ChemIDplus
butorphanolum ChemIDplus
Synonyms Sources
(−)-17-(cyclobutylmethyl)morphinan-3,14-diol ChemIDplus
(−)-butorphanol ChEBI
(−)-N-cyclobutylmethyl-3,14-dihydroxymorphinan ChEBI
BUTORPHANOL ChEMBL
Butorphanol KEGG COMPOUND
Manual Xrefs Databases
1780 VSDB
454 DrugCentral
Butorphanol Wikipedia
C06863 KEGG COMPOUND
D03197 KEGG DRUG
DB00611 DrugBank
DE2243961 Patent
US3775414 Patent
US3819635 Patent
View more database links
Registry Numbers Types Sources
42408-82-2 CAS Registry Number KEGG COMPOUND
42408-82-2 CAS Registry Number ChemIDplus
8134188 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
6114178 PubMed citation ChEMBL
6166748 PubMed citation ChEMBL
6767032 PubMed citation ChEMBL
6796691 PubMed citation ChEMBL
7192744 PubMed citation ChEMBL
Last Modified
22 February 2017