Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:51 UTC |
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Update Date | 2020-02-26 21:40:52 UTC |
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HMDB ID | HMDB0015057 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Buprenorphine |
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Description | Buprenorphine, also known as buprenorfina or temgesic, 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. Buprenorphine is a very strong basic compound (based on its pKa). In humans, buprenorphine is involved in buprenorphine action pathway. Individuals must therefore be in a state of mild to moderate withdrawal before starting therapy with buprenorphine. Buprenorphine is a potentially toxic compound. |
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Structure | |
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Synonyms | Value | Source |
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(-)-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 |
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Chemical Formula | C29H41NO4 |
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Average Molecular Weight | 467.6401 |
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Monoisotopic Molecular Weight | 467.303558805 |
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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 |
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Traditional Name | buprenorphine |
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CAS Registry Number | 52485-79-7 |
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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 |
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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 |
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InChI Key | RMRJXGBAOAMLHD-IHFGGWKQSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Phenanthrenes and derivatives |
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Sub Class | Not Available |
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Direct Parent | Phenanthrenes and derivatives |
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Alternative Parents | |
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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
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Route of exposure: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.017 g/L | Not Available | LogP | 3.8 | Not Available |
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Predicted Properties | |
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