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CHEBI:3216 - buprenorphine

Default Structure
ChEBI IDCHEBI:3216
ChEBI Namebuprenorphine
Stars
DefinitionA morphinane alkaloid that is 7,8-dihydromorphine 6-O-methyl ether in which positions 6 and 14 are joined by a -CH2CH2- bridge, one of the hydrogens of the N-methyl group is substituted by cyclopropyl, and a hydrogen at position 7 is substituted by a 2-hydroxy-3,3-dimethylbutan-2-yl group. It is highly effective for the treatment of opioid use disorder and is also increasingly being used in the treatment of chronic pain.
Secondary ChEBI IDsCHEBI:143179, CHEBI:166254, CHEBI:453763, CHEBI:489640, CHEBI:656608
Last Modified7 January 2021
DownloadsMolfile
FormulaC29H41NO4
Net Charge0
Average Mass467.650
Monoisotopic Mass467.30356
SMILES[H][C@]1([C@](C)(O)C(C)(C)C)C[C@@]23CC[C@]1(OC)[C@@H]1Oc4c(O)ccc5c4[C@@]12CCN(CC1CC1)[C@@H]3C5
InChIInChI=1S/C29H41NO4/c1-25(2,3)26(4,32)20-15-27-10-11-29(20,33-5)24-28(27)12-13-30(16-17-6-7-17)21(27)14-18-8-9-19(31)23(34-24)22(18)28/h8-9,17,20-21,24,31-32H,6-7,10-16H2,1-5H3/t20-,21-,24-,26+,27-,28+,29-/m1/s1
InChIKeyRMRJXGBAOAMLHD-IHFGGWKQSA-N
Wikipedia
Roles Classification
Biological Roles:
mu-opioid receptor agonist  A compound that exhibits agonist activity at the μ-opioid receptor.
opioid analgesic  A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
kappa-opioid receptor antagonist  Any compound that exhibits antagonist activity at the κ-opioid receptor.
delta-opioid receptor antagonist  Any compound that exhibits antagonist activity at the δ-opioid receptor.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
mu-opioid receptor agonist  A compound that exhibits agonist activity at the μ-opioid receptor.
opioid analgesic  A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
kappa-opioid receptor antagonist  Any compound that exhibits antagonist activity at the κ-opioid receptor.
delta-opioid receptor antagonist  Any compound that exhibits antagonist activity at the δ-opioid receptor.
ChEBI Ontology
Outgoing Relation(s)
buprenorphine (CHEBI:3216) has role opioid analgesic (CHEBI:35482)
buprenorphine (CHEBI:3216) has role δ-opioid receptor antagonist (CHEBI:59283)
buprenorphine (CHEBI:3216) has role κ-opioid receptor antagonist (CHEBI:167165)
buprenorphine (CHEBI:3216) has role μ-opioid receptor agonist (CHEBI:55322)
buprenorphine (CHEBI:3216) is a morphinane alkaloid (CHEBI:25418)
Incoming Relation(s)
buprenorphine hydrochloride (CHEBI:652822) has part buprenorphine (CHEBI:3216)
IUPAC Name 
(5α,6β,14β,18R)-17-(cyclopropylmethyl)-18-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-6-methoxy-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-3-ol
INNs  Source
buprenorfinaChemIDplus
buprenorphineChemIDplus
buprenorphinumChemIDplus
Synonyms  Source
17-cyclopropylmethyl-4,5α-epoxy-7α-((S)-1-hydroxy-1,2,2-trimethylpropyl)-6-methoxy-6,14-endo-ethanomorphinan-3-olChemIDplus
21-cyclopropyl-7α-[(S)-1-hydroxy-1,2,2-trimethylpropyl]-6,14-endo-ethano-6,7,8,14-tetrahydrooripavineChemIDplus
2-[3-cyclopropylmethyl-11-hydroxy-15-methoxy-(14R)-13-oxa-3-azahexacyclo[13.2.2.12,8.01,6.06,14.07,12]icosa-7,9,11-trien-16-yl]-3,3-dimethyl-2-butanolChEMBL
2-(N-cyclopropylmethyl-4,5α-epoxy-3-hydroxy-6-methoxy-6,14-endo-ethanomorphinan-6α-yl)-3,3-dimethyl-2-butanolChemIDplus
(−)-buprenorphineChEBI
BuprenorphineKEGG COMPOUND
Manual XrefsDatabases
1789VSDB
434DrugCentral
559124ChemSpider
BuprenorphineWikipedia
C08007KEGG COMPOUND
CPD-22086MetaCyc
D07132KEGG DRUG
DB00921DrugBank
GB1136214Patent
HMDB0015057HMDB
US3433791Patent
Registry NumbersSources
Beilstein:6182863Beilstein
CAS:52485-79-7ChemIDplus
CAS:52485-79-7KEGG COMPOUND
CAS:52485-79-7NIST Chemistry WebBook
Citations