Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 17:45:12 UTC |
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Update Date | 2022-03-07 02:53:06 UTC |
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HMDB ID | HMDB0031751 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | y-Morphine |
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Description | y-Morphine, also known as 2,2'bimorphine or dehydromorphine, belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic. Based on a literature review a small amount of articles have been published on y-Morphine. |
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Structure | CN1CCC23C4OC5=C2C(CC1C3C=CC4O)=CC(=C5O)C1=C(O)C2=C3C(CC4C5C=CC(O)C(O2)C35CCN4C)=C1 InChI=1S/C34H36N2O6/c1-35-9-7-33-19-3-5-23(37)31(33)41-29-25(33)15(13-21(19)35)11-17(27(29)39)18-12-16-14-22-20-4-6-24(38)32-34(20,8-10-36(22)2)26(16)30(42-32)28(18)40/h3-6,11-12,19-24,31-32,37-40H,7-10,13-14H2,1-2H3 |
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Synonyms | Value | Source |
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2,2'-Bimorphine | HMDB | 2,2'Bimorphine | HMDB | 7,7',8,8'-Tetrahydro-4,5:4',5'-diepoxy-17,17'-dimethyl[2,2'-bimorphinan], 9ci | HMDB | Dehydromorphine | HMDB | Oxydimorphine | HMDB | Oxymorphine | HMDB | Pseudomorphine | HMDB |
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Chemical Formula | C34H36N2O6 |
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Average Molecular Weight | 568.6594 |
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Monoisotopic Molecular Weight | 568.257336894 |
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IUPAC Name | 9-{10,14-dihydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7,9,11(18),15-tetraen-9-yl}-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7,9,11(18),15-tetraene-10,14-diol |
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Traditional Name | pseudomorphine |
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CAS Registry Number | 125-24-6 |
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SMILES | CN1CCC23C4OC5=C2C(CC1C3C=CC4O)=CC(=C5O)C1=C(O)C2=C3C(CC4C5C=CC(O)C(O2)C35CCN4C)=C1 |
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InChI Identifier | InChI=1S/C34H36N2O6/c1-35-9-7-33-19-3-5-23(37)31(33)41-29-25(33)15(13-21(19)35)11-17(27(29)39)18-12-16-14-22-20-4-6-24(38)32-34(20,8-10-36(22)2)26(16)30(42-32)28(18)40/h3-6,11-12,19-24,31-32,37-40H,7-10,13-14H2,1-2H3 |
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InChI Key | FOJYFDFNGPRXDR-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic. |
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Kingdom | Organic compounds |
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Super Class | Alkaloids and derivatives |
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Class | Morphinans |
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Sub Class | Not Available |
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Direct Parent | Morphinans |
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Alternative Parents | |
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Substituents | - Neolignan skeleton
- Morphinan
- Phenanthrene
- Tetralin
- Coumaran
- Alkyl aryl ether
- Aralkylamine
- Piperidine
- Benzenoid
- Secondary alcohol
- Tertiary amine
- Tertiary aliphatic amine
- Oxacycle
- Ether
- Azacycle
- Organoheterocyclic compound
- Organic nitrogen compound
- Alcohol
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Organic oxygen compound
- Amine
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 330 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Retention Times UnderivatizedChromatographic Method | Retention Time | Reference |
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Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022. | 2.46 minutes | 32390414 | Predicted by Siyang on May 30, 2022 | 10.8484 minutes | 33406817 | Predicted by Siyang using ReTip algorithm on June 8, 2022 | 5.09 minutes | 32390414 | AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid | 248.7 seconds | 40023050 | Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid | 835.5 seconds | 40023050 | Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid | 192.3 seconds | 40023050 | Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid | 165.2 seconds | 40023050 | Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid | 185.8 seconds | 40023050 | RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 77.0 seconds | 40023050 | Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid | 308.5 seconds | 40023050 | BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid | 333.3 seconds | 40023050 | HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate) | 1066.8 seconds | 40023050 | UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid | 744.7 seconds | 40023050 | BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid | 246.8 seconds | 40023050 | UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid | 894.7 seconds | 40023050 | SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 223.4 seconds | 40023050 | RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 261.9 seconds | 40023050 | MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate | 522.7 seconds | 40023050 | KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA | 699.5 seconds | 40023050 | Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water | 93.3 seconds | 40023050 |
Predicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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y-Morphine,1TMS,isomer #1 | CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O)OC6C(O[Si](C)(C)C)C=CC9C(C7)N(C)CCC896)C(O)=C4OC2C(O)C=CC3C1C5 | 4847.0 | Semi standard non polar | 33892256 | y-Morphine,1TMS,isomer #2 | CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O[Si](C)(C)C)OC6C(O)C=CC9C(C7)N(C)CCC896)C(O)=C4OC2C(O)C=CC3C1C5 | 4872.5 | Semi standard non polar | 33892256 | y-Morphine,2TMS,isomer #1 | CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O[Si](C)(C)C)OC6C(O[Si](C)(C)C)C=CC9C(C7)N(C)CCC896)C(O)=C4OC2C(O)C=CC3C1C5 | 4774.2 | Semi standard non polar | 33892256 | y-Morphine,2TMS,isomer #2 | CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O)OC6C(O[Si](C)(C)C)C=CC9C(C7)N(C)CCC896)C(O[Si](C)(C)C)=C4OC2C(O)C=CC3C1C5 | 4772.9 | Semi standard non polar | 33892256 | y-Morphine,2TMS,isomer #3 | CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O)OC6C(O[Si](C)(C)C)C=CC9C(C7)N(C)CCC896)C(O)=C4OC2C(O[Si](C)(C)C)C=CC3C1C5 | 4739.4 | Semi standard non polar | 33892256 | y-Morphine,2TMS,isomer #4 | CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O[Si](C)(C)C)OC6C(O)C=CC9C(C7)N(C)CCC896)C(O[Si](C)(C)C)=C4OC2C(O)C=CC3C1C5 | 4803.4 | Semi standard non polar | 33892256 | y-Morphine,3TMS,isomer #1 | CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O[Si](C)(C)C)OC6C(O[Si](C)(C)C)C=CC9C(C7)N(C)CCC896)C(O[Si](C)(C)C)=C4OC2C(O)C=CC3C1C5 | 4730.1 | Semi standard non polar | 33892256 | y-Morphine,3TMS,isomer #2 | CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O[Si](C)(C)C)OC6C(O[Si](C)(C)C)C=CC9C(C7)N(C)CCC896)C(O)=C4OC2C(O[Si](C)(C)C)C=CC3C1C5 | 4700.2 | Semi standard non polar | 33892256 | y-Morphine,4TMS,isomer #1 | CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O[Si](C)(C)C)OC6C(O[Si](C)(C)C)C=CC9C(C7)N(C)CCC896)C(O[Si](C)(C)C)=C4OC2C(O[Si](C)(C)C)C=CC3C1C5 | 4665.4 | Semi standard non polar | 33892256 | y-Morphine,1TBDMS,isomer #1 | CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O)OC6C(O[Si](C)(C)C(C)(C)C)C=CC9C(C7)N(C)CCC896)C(O)=C4OC2C(O)C=CC3C1C5 | 5025.4 | Semi standard non polar | 33892256 | y-Morphine,1TBDMS,isomer #2 | CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O[Si](C)(C)C(C)(C)C)OC6C(O)C=CC9C(C7)N(C)CCC896)C(O)=C4OC2C(O)C=CC3C1C5 | 5056.9 | Semi standard non polar | 33892256 | y-Morphine,2TBDMS,isomer #1 | CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O[Si](C)(C)C(C)(C)C)OC6C(O[Si](C)(C)C(C)(C)C)C=CC9C(C7)N(C)CCC896)C(O)=C4OC2C(O)C=CC3C1C5 | 5129.9 | Semi standard non polar | 33892256 | y-Morphine,2TBDMS,isomer #2 | CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O)OC6C(O[Si](C)(C)C(C)(C)C)C=CC9C(C7)N(C)CCC896)C(O[Si](C)(C)C(C)(C)C)=C4OC2C(O)C=CC3C1C5 | 5127.7 | Semi standard non polar | 33892256 | y-Morphine,2TBDMS,isomer #3 | CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O)OC6C(O[Si](C)(C)C(C)(C)C)C=CC9C(C7)N(C)CCC896)C(O)=C4OC2C(O[Si](C)(C)C(C)(C)C)C=CC3C1C5 | 5092.6 | Semi standard non polar | 33892256 | y-Morphine,2TBDMS,isomer #4 | CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O[Si](C)(C)C(C)(C)C)OC6C(O)C=CC9C(C7)N(C)CCC896)C(O[Si](C)(C)C(C)(C)C)=C4OC2C(O)C=CC3C1C5 | 5166.0 | Semi standard non polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - y-Morphine GC-MS (Non-derivatized) - 70eV, Positive | splash10-0v00-2000090000-174325cbb89f345f7805 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - y-Morphine GC-MS (1 TMS) - 70eV, Positive | splash10-00b9-9000045000-e08b9c116733de3d4a01 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - y-Morphine GC-MS ("y-Morphine,1TMS,#1" TMS) - 70eV, Positive | Not Available | 2021-10-14 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - y-Morphine GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - y-Morphine GC-MS (TMS_2_1) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - y-Morphine GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - y-Morphine GC-MS (TMS_2_3) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - y-Morphine GC-MS (TMS_2_4) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - y-Morphine GC-MS (TMS_3_1) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - y-Morphine GC-MS (TMS_3_2) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - y-Morphine GC-MS (TMS_4_1) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - y-Morphine GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - y-Morphine GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - y-Morphine GC-MS (TBDMS_2_1) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - y-Morphine GC-MS (TBDMS_2_2) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - y-Morphine GC-MS (TBDMS_2_3) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - y-Morphine GC-MS (TBDMS_2_4) - 70eV, Positive | Not Available | 2021-10-15 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - y-Morphine 10V, Positive-QTOF | splash10-014i-0000090000-3a67c2c327b70a10015a | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - y-Morphine 20V, Positive-QTOF | splash10-014i-0030090000-b6150fa06b54d6f31d4e | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - y-Morphine 40V, Positive-QTOF | splash10-0006-3090150000-ed2bfee9e9434880ef88 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - y-Morphine 10V, Negative-QTOF | splash10-014i-0000090000-05f51fdb3f7ad93b6c7e | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - y-Morphine 20V, Negative-QTOF | splash10-0159-0060090000-3fa0169a42bb58fc17b7 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - y-Morphine 40V, Negative-QTOF | splash10-003r-0090010000-d1384d9ad3412100559d | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - y-Morphine 10V, Positive-QTOF | splash10-014i-0000090000-524a091d90240fb5cd47 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - y-Morphine 20V, Positive-QTOF | splash10-014r-0000090000-a3820722ce37a2ff5d67 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - y-Morphine 40V, Positive-QTOF | splash10-01p9-0000190000-37f5f984f804e4ce51be | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - y-Morphine 10V, Negative-QTOF | splash10-014i-0000090000-6312a1c194c99bba2b01 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - y-Morphine 20V, Negative-QTOF | splash10-014i-0000090000-e2fc2aed931f92c40146 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - y-Morphine 40V, Negative-QTOF | splash10-00kr-0000090000-ec077ce6ee35b4cfa18e | 2021-09-25 | Wishart Lab | View Spectrum |
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- Brusick D, Matheson D, Jagannath D, Braude M, Brockman H, Hung C: Genetic screening of compounds used in drug abuse treatment. III. LAAM. Drug Chem Toxicol. 1981;4(1):19-35. [PubMed:6455284 ]
- Shook JE, Watkins WD, Camporesi EM: Differential roles of opioid receptors in respiration, respiratory disease, and opiate-induced respiratory depression. Am Rev Respir Dis. 1990 Oct;142(4):895-909. [PubMed:2171388 ]
- Pittman KA, Smyth RD, Mayol RF: Serum levels of butorphanol by radioimmunoassay. J Pharm Sci. 1980 Feb;69(2):160-3. [PubMed:7359315 ]
- Proksa B: Separation of morphine and its oxidation products by capillary zone electrophoresis. J Pharm Biomed Anal. 1999 Jun;20(1-2):179-83. [PubMed:10704021 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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