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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.
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.
opioid analgesic  A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
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.
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.
opioid analgesic  A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
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