EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:3242 - butorphanol

ChEBI IDCHEBI:3242
ChEBI Namebutorphanol
Stars
DefinitionLevorphanol 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.
Secondary ChEBI IDCHEBI:145838
Last Modified22 February 2017
DownloadsMolfile
FormulaC21H29NO2
Net Charge0
Average Mass327.468
Monoisotopic Mass327.21983
SMILESOc1ccc2c(c1)[C@@]13CCCC[C@@]1(O)[C@@H](C2)N(CC1CCC1)CC3
InChIInChI=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
InChIKeyIFKLAQQSCNILHL-QHAWAJNXSA-N
Wikipedia
Roles Classification
Biological Roles:
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 μ-opioid receptor.
kappa-opioid receptor agonist  A compound that exhibits agonist activity at the κ-opioid receptor.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
opioid analgesic  A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
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.
mu-opioid receptor agonist  A compound that exhibits agonist activity at the μ-opioid receptor.
kappa-opioid receptor agonist  A compound that exhibits agonist activity at the κ-opioid receptor.
ChEBI Ontology
Outgoing Relation(s)
butorphanol (CHEBI:3242) has role antitussive (CHEBI:51177)
butorphanol (CHEBI:3242) has role opioid analgesic (CHEBI:35482)
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) is a morphinane alkaloid (CHEBI:25418)
Incoming Relation(s)
butorphanol D-tartrate (CHEBI:3243) has part butorphanol (CHEBI:3242)
IUPAC Name 
17-(cyclobutylmethyl)morphinan-3,14-diol
INNs  Source
butorphanolChemIDplus
butorfanolChemIDplus
butorphanolumChemIDplus
Synonyms  Source
ButorphanolKEGG COMPOUND
BUTORPHANOLChEMBL
(−)-butorphanolChEBI
(−)-17-(cyclobutylmethyl)morphinan-3,14-diolChemIDplus
(−)-N-cyclobutylmethyl-3,14-dihydroxymorphinanChEBI
Manual XrefsDatabases
C06863KEGG COMPOUND
DB00611DrugBank
D03197KEGG DRUG
DE2243961Patent
US3819635Patent
US3775414Patent
ButorphanolWikipedia
454DrugCentral
1780VSDB
Registry NumbersSources
Beilstein:8134188Beilstein
CAS:42408-82-2KEGG COMPOUND
CAS:42408-82-2ChemIDplus
Citations