ContaminantDB: Buprenorphine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (4)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:58 UTC

Update Date

2026-03-31 19:08:03 UTC

Accession Number

CHEM002303

Identification

Common Name

Buprenorphine

Class

Small Molecule

Description

Buprenorphine is a derivative of the opioid alkaloid thebaine that is a more potent (25 - 40 times) and longer lasting analgesic than morphine. It appears to act as a partial agonist at mu and kappa opioid receptors and as an antagonist at delta receptors. The lack of delta-agonist activity has been suggested to account for the observation that buprenorphine tolerance may not develop with chronic use. [PubChem]

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Amine
Analgesic, Opioid
Drug
Ether
Metabolite
Narcotic
Narcotic Antagonist
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-Buprenorphine	ChEBI
17-Cyclopropylmethyl-4,5alpha-epoxy-7alpha-((S)-1-hydroxy-1,2,2-trimethylpropyl)-6-methoxy-6,14-endo-ethanomorphinan-3-ol	ChEBI
2-(N-Cyclopropylmethyl-4,5alpha-epoxy-3-hydroxy-6-methoxy-6,14-endo-ethanomorphinan-6alpha-yl)-3,3-dimethyl-2-butanol	ChEBI
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	ChEBI
21-Cyclopropyl-7alpha-[(S)-1-hydroxy-1,2,2-trimethylpropyl]-6,14-endo-ethano-6,7,8,14-tetrahydrooripavine	ChEBI
Buprenorfina	ChEBI
Buprenorphinum	ChEBI
Temgesic	Kegg
17-Cyclopropylmethyl-4,5a-epoxy-7a-((S)-1-hydroxy-1,2,2-trimethylpropyl)-6-methoxy-6,14-endo-ethanomorphinan-3-ol	Generator
17-Cyclopropylmethyl-4,5α-epoxy-7α-((S)-1-hydroxy-1,2,2-trimethylpropyl)-6-methoxy-6,14-endo-ethanomorphinan-3-ol	Generator
2-(N-Cyclopropylmethyl-4,5a-epoxy-3-hydroxy-6-methoxy-6,14-endo-ethanomorphinan-6a-yl)-3,3-dimethyl-2-butanol	Generator
2-(N-Cyclopropylmethyl-4,5α-epoxy-3-hydroxy-6-methoxy-6,14-endo-ethanomorphinan-6α-yl)-3,3-dimethyl-2-butanol	Generator
21-Cyclopropyl-7a-[(S)-1-hydroxy-1,2,2-trimethylpropyl]-6,14-endo-ethano-6,7,8,14-tetrahydrooripavine	Generator
21-Cyclopropyl-7α-[(S)-1-hydroxy-1,2,2-trimethylpropyl]-6,14-endo-ethano-6,7,8,14-tetrahydrooripavine	Generator
Buprenophine	HMDB
Essex brand OF buprenorphine hydrochloride	HMDB
Key brand OF buprenorphine hydrochloride	HMDB
Reckitt benckiser brand OF buprenorphine hydrochloride	HMDB
Buprex	HMDB
Temgésic	HMDB
Buprenorphine hydrochloride	HMDB
Grünenthal brand OF buprenorphine	HMDB
Reckitt and colman brand 2 OF buprenorphine hydrochloride	HMDB
Buprenex	HMDB
Reckitt and colman brand 1 OF buprenorphine hydrochloride	HMDB
Schering plough brand OF buprenorphine hydrochloride	HMDB
Buprenorphine grünenthal brand	HMDB
Prefin	HMDB
RX-6029-m	HMDB
Schering-plough brand OF buprenorphine hydrochloride	HMDB
Grünenthal brand OF buprenorphine hydrochloride	HMDB
Hydrochloride, buprenorphine	HMDB
RX 6029 m	HMDB
Reckitt brand OF buprenorphine hydrochloride	HMDB
Subutex	HMDB

Chemical Formula

C₂₉H₄₁NO₄

Average Molecular Mass

467.640 g/mol

Monoisotopic Mass

467.304 g/mol

CAS Registry Number

52485-79-7

IUPAC Name

(1S,2R,6S,14R,15R,16R)-3-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.1²,⁸.0¹,⁶.0⁶,¹⁴.0⁷,¹²]icosa-7,9,11-trien-11-ol

Traditional Name

buprenorphine

SMILES

CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O)C(C)(C)C)[C@H]1CC4=C5C(O[C@@H]2[C@@]35CCN1CC1CC1)=C(O)C=C4

InChI Identifier

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

InChI Key

RMRJXGBAOAMLHD-IHFGGWKQSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Not Available

Direct Parent

Phenanthrenes and derivatives

Alternative Parents

Substituents

Phenanthrene
Azaspirodecane
Tetralin
Coumaran
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Piperidine
Tertiary alcohol
Tertiary amine
Tertiary aliphatic amine
Dialkyl ether
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Alcohol
Organopnictogen compound
Hydrocarbon derivative
Amine
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

morphinane alkaloid (CHEBI:3216 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	1.68e-02 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.017 g/L	ALOGPS
logP	4.53	ALOGPS
logP	3.55	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	7.5	ChemAxon
pKa (Strongest Basic)	12.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.16 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	131.76 m³·mol⁻¹	ChemAxon
Polarizability	53.11 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9004200000-95c5673aa686eb387e74	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-05g4-9000120000-df9796e1ae0815a47d9b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("Buprenorphine,1TMS,#1" TMS) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-1000-3000900000-e02fba1e40b85e61b83c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9001400000-eed215cb420d242b3d55	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-817bab94cec1acd1c7e8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0001900000-285d935fade7fca577c3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-2005900000-d8e7f724df7328e6815e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ika-2009100000-36ff69a17a3778cc0036	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0000900000-6f5d221eee7743008b27	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0000900000-58cbb866de1b4c36845e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0000900000-c56569d00471b33e2382	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000900000-60c120f6e661a422e31f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0000900000-60c120f6e661a422e31f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0000900000-e4673887dac8f5daaf68	Spectrum

Toxicity Profile

Route of Exposure

31% bioavailability (sublingual). Sublingual absorption is also dependent on pH. The length of time the tablet is under the tongue has little effect on absorption. Although buprenorphine is rapidly absorbed from the oral mucosa, the absorption into the systemic is slower. The time to reach peak plasma concentration (Tmax) varies between individuals (range of 40 minutes to 3.5 hours). How buprenorphine is formulated does not affect this pharmacokinetic parameter. It also undergoes extensive first-pass metabolism and as a consequence, has very low oral bioavailability. Coadministration with naloxone does not effect the pharmacokinetics of buprenorphine.

Mechanism of Toxicity

Buprenorphine's analgesic effect is due to partial agonist activity at mu-opioid receptors. Buprenorphine is also a kappa-opioid receptor antagonist. The partial agonist activity means that opioid receptor antagonists (e.g., an antidote such as naloxone) only partially reverse the effects of buprenorphine. The binding to the mu and kappa receptors results in hyperpolarization and reduced neuronal excitability. Furthermore, buprenorphine slowly dissociates from its receptor. This observation would account for the longer duration of action compared to morphine, the unpredictability of its reversal by opioid antagonists, and its low level of manifest physical dependence. Its receptor fixation half life is 40 minutes which is significantly longer than morphine (milliseconds).

Metabolism

Hepatic. Buprenorphine undergoes both N-dealkylation to norbuprenorphine and glucuronidation. The N-dealkylation pathway is mediated by cytochrome P-450 3A4 isozyme. Norbuprenorphine, an active metabolite and has one-fifth of the pharmacologic activity of the parent compound, can further undergo glucuronidation. Route of Elimination: Buprenorphine, like morphine and other phenolic opioid analgesics, is metabolized by the liver and its clearance is related to hepatic blood flow. It is primarily eliminated via feces (as free forms of buprenorphine and norbuprenorphine) while 10 - 30% of the dose is excreted in urine (as conjugated forms of buprenorphine and norbuprenorphine). Half Life: IV administration, 0.3 mg = 1.2 - 7.2 hours (mean 2.2 hours); Sublingual administration = 37 hours.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the treatment of moderate to severe pain, peri-operative analgesia, and opioid dependence.

Minimum Risk Level

Not Available

Health Effects

Medical problems can include congested lungs, liver disease, tetanus, infection of the heart valves, skin abscesses, anemia and pneumonia. Death can occur from overdose.

Symptoms

Manifestations of acute overdose include pinpoint pupils, sedation, hypotension, respiratory depression and death.

Treatment

The respiratory and cardiac status of the patient should be monitored carefully. In the event of depression of respiratory or cardiac function, primary attention should be given to the re-establishment of adequate respiratory exchange through provision of a patent airway and institution of assisted or controlled ventilation. Oxygen, intravenous fluids, vasopressors, and other supportive measures should be employed as indicated. In the case of overdose, the primary management should be the re-establishment of adequate ventilation with mechanical assistance of respiration, if required. Naloxone may not be effective in reversing any respiratory depression produced by buprenorphine. High doses of naloxone hydrochloride, 10-35 mg/70 kg may be of limited value in the management of buprenorphine overdose. Doxapram (a respiratory stimulant) also has been used. (5)

Concentrations

Not Available

External Links

DrugBank ID

DB00921

HMDB ID

HMDB0015057

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

CPD-22086

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Kazuhisa Ninomiya, Yasuhiro Fukushima, Mutsuo Okumura, Yuko Hosokawa, “Buprenorphine percutaneous absorption preparation.” U.S. Patent US6090405, issued August, 1992.

MSDS

Link

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10649968

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11303059

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15181649

4. https://www.ncbi.nlm.nih.gov/pubmed/?term=15781180

5. https://www.ncbi.nlm.nih.gov/pubmed/?term=16642964

6. https://www.ncbi.nlm.nih.gov/pubmed/?term=16650985

7. https://www.ncbi.nlm.nih.gov/pubmed/?term=17887741

8. https://www.ncbi.nlm.nih.gov/pubmed/?term=18997874

9. https://www.ncbi.nlm.nih.gov/pubmed/?term=19402772