CHEBI:3216 - buprenorphine

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ChEBI Name buprenorphine
ChEBI ID CHEBI:3216
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:489640, CHEBI:143179, CHEBI:453763, CHEBI:166254, CHEBI:656608
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Formula C29H41NO4
Net Charge 0
Average Mass 467.64010
Monoisotopic Mass 467.30356
InChI InChI=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
InChIKey RMRJXGBAOAMLHD-IHFGGWKQSA-N
SMILES [H][C@@]1(C[C@]23CC[C@]1(OC)[C@@H]1Oc4c(O)ccc5C[C@H]2N(CC[C@@]31c45)CC1CC1)[C@](C)(O)C(C)(C)C
Roles Classification
Biological Role(s): kappa-opioid receptor antagonist
Any compound that exhibits antagonist activity at the kappa-opioid receptor.
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.
delta-opioid receptor antagonist
Any compound that exhibits antagonist activity at the delta-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): kappa-opioid receptor antagonist
Any compound that exhibits antagonist activity at the kappa-opioid receptor.
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.
delta-opioid receptor antagonist
Any compound that exhibits antagonist activity at the delta-opioid receptor.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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) has role opioid analgesic (CHEBI:35482)
buprenorphine (CHEBI:3216) is a morphinane alkaloid (CHEBI:25418)
Incoming buprenorphine hydrochlorie (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 Sources
buprenorfina ChemIDplus
buprenorphine ChemIDplus
buprenorphinum ChemIDplus
Synonyms Sources
(−)-buprenorphine ChEBI
17-cyclopropylmethyl-4,5α-epoxy-7α-((S)-1-hydroxy-1,2,2-trimethylpropyl)-6-methoxy-6,14-endo-ethanomorphinan-3-ol ChemIDplus
2-(N-cyclopropylmethyl-4,5α-epoxy-3-hydroxy-6-methoxy-6,14-endo-ethanomorphinan-6α-yl)-3,3-dimethyl-2-butanol ChemIDplus
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-butanol ChEMBL
21-cyclopropyl-7α-[(S)-1-hydroxy-1,2,2-trimethylpropyl]-6,14-endo-ethano-6,7,8,14-tetrahydrooripavine ChemIDplus
Buprenorphine KEGG COMPOUND
Manual Xrefs Databases
1789 VSDB
434 DrugCentral
559124 ChemSpider
Buprenorphine Wikipedia
C08007 KEGG COMPOUND
CPD-22086 MetaCyc
D07132 KEGG DRUG
DB00921 DrugBank
GB1136214 Patent
HMDB0015057 HMDB
US3433791 Patent
View more database links
Registry Numbers Types Sources
52485-79-7 CAS Registry Number KEGG COMPOUND
52485-79-7 CAS Registry Number ChemIDplus
52485-79-7 CAS Registry Number NIST Chemistry WebBook
6182863 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
10649968 PubMed citation ChEMBL
11303059 PubMed citation Europe PMC
15181649 PubMed citation Europe PMC
15781180 PubMed citation Europe PMC
16642964 PubMed citation Europe PMC
16650985 PubMed citation ChEMBL
17887741 PubMed citation ChEMBL
18997874 PubMed citation Europe PMC
19402772 PubMed citation Europe PMC
32925232 PubMed citation Europe PMC
33378137 PubMed citation Europe PMC
PMC7711199 PubMed Central citation Europe PMC
Last Modified
07 January 2021
General Comment
2011-03-17 Buprenorphine is a more potent and longer lasting analgesic than morphine.