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CHEBI:3216 - buprenorphine

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:489640, CHEBI:143179, CHEBI:453763, CHEBI:166254, CHEBI:656608
Supplier Information
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Formula C29H41NO4
Net Charge 0
Average Mass 467.64010
Monoisotopic Mass 467.304
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): 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.
delta-opioid receptor antagonist
A 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): 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.
delta-opioid receptor antagonist
A 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 agonist (CHEBI:59282)
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
Database Links Databases
C08007 KEGG COMPOUND
D07132 KEGG DRUG
DB00921 DrugBank
GB1136214 Patent
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
6182863 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
10649968 PubMed citation ChEMBL
16650985 PubMed citation ChEMBL
17887741 PubMed citation ChEMBL
Last Modified
17 March 2011
General Comment
2011-03-17 Buprenorphine is a more potent and longer lasting analgesic than morphine.