| Record Information |
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| Version | 5.0 |
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| Status | Expected but not Quantified |
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| Creation Date | 2013-06-12 17:33:29 UTC |
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| Update Date | 2021-09-14 15:19:57 UTC |
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| HMDB ID | HMDB0060548 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Dihydromorphine |
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| Description | Dihydromorphine, also known as paramorphan or 6α-hydromorphol, 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. Dihydromorphine is a very strong basic compound (based on its pKa). In humans, dihydromorphine is involved in dihydromorphine action pathway. Dihydromorphine acts as an agonist at the μ-opioid (mu), δ-opioid (delta) and κ-opioid (kappa) receptors. As with nicomorphine, MDMA, heroin (DEA 2013 production quota: 25 grammes) and the like, dihydromorphine is also used in research such as that mentioned above in properly licensed facilities; Form 225, the most common and least expensive individual researcher's license, does not include Schedule I so the lab must have a higher-level DEA registration As with other licit opioids used for medical purposes in other countries, including even much weaker opioids like nicocodeine, benzylmorphine, and tilidine, the reason for dihydromorphine being in Schedule I is that it was not in medical use in the US at time the Controlled Substances Act of 1970 was drawn up. Dihydromorphine's onset of action is more rapid than morphine and it also tends to have a longer duration of action, generally 4–7 hours. In comparison, the relative potency of dihydrocodeine is 1.15 times that of codeine. Dihydromorphine is a moderately strong analgesic and is used clinically in the treatment of pain and also is an active metabolite of the analgesic opioid drug dihydrocodeine. Dihydromorphine, often labelled with the isotope tritium in the form of [3H]-dihydromorphine, is used in scientific research to study binding of the opioid receptors in the nervous system. Under the Controlled Substances Act, dihydromorphine is listed as a Schedule I substance along with heroin. |
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| Structure | [H][C@@]12OC3=C4C(C[C@@]5([H])N(C)CC[C@@]14[C@@]5([H])CC[C@@H]2O)=CC=C3O InChI=1S/C17H21NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2,4,10-11,13,16,19-20H,3,5-8H2,1H3/t10-,11+,13-,16-,17-/m0/s1 |
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| Synonyms | | Value | Source |
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| Paramorphan | HMDB | | Paramorfan | HMDB | | (5alpha,6alpha)-4,5-Epoxy-17-methylmorphinan-3,6-diol | HMDB | | (5Α,6α)-4,5-epoxy-17-methylmorphinan-3,6-diol | HMDB | | 6alpha-7,8-Dihydromorphine | HMDB | | 6alpha-Hydromorphol | HMDB | | 6Α-7,8-dihydromorphine | HMDB | | 6Α-hydromorphol | HMDB | | 7,8-Dihydromorphine | HMDB | | DHM | HMDB | | Hydromorphine | HMDB | | alpha-Dihydromorphine | HMDB | | Α-dihydromorphine | HMDB | | Dihydromorphine | HMDB |
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| Chemical Formula | C17H21NO3 |
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| Average Molecular Weight | 287.3535 |
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| Monoisotopic Molecular Weight | 287.152143543 |
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| IUPAC Name | (1S,5R,13R,14S,17R)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-triene-10,14-diol |
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| Traditional Name | (1S,5R,13R,14S,17R)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-triene-10,14-diol |
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| CAS Registry Number | 509-60-4 |
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| SMILES | [H][C@@]12OC3=C4C(C[C@@]5([H])N(C)CC[C@@]14[C@@]5([H])CC[C@@H]2O)=CC=C3O |
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| InChI Identifier | InChI=1S/C17H21NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2,4,10-11,13,16,19-20H,3,5-8H2,1H3/t10-,11+,13-,16-,17-/m0/s1 |
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| InChI Key | IJVCSMSMFSCRME-KBQPJGBKSA-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 | - Morphinan
- Phenanthrene
- Tetralin
- Coumaran
- Alkyl aryl ether
- 1-hydroxy-2-unsubstituted benzenoid
- Aralkylamine
- Piperidine
- Benzenoid
- Cyclic alcohol
- Secondary alcohol
- Tertiary aliphatic amine
- Tertiary amine
- Ether
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Organopnictogen compound
- Amine
- Alcohol
- 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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| Not Available | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Experimental Molecular Properties | | Property | Value | Reference |
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| Melting Point | Not Available | 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 | Experimental Collision Cross Sections| Adduct Type | Data Source | CCS Value (Å2) | Reference |
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| [M+H]+ | CBM | 163.6 | 30932474 |
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| Predicted Molecular Properties | |
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| Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Retention Times Underivatized| Chromatographic 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. | 2.95 minutes | 32390414 | | Predicted by Siyang on May 30, 2022 | 9.8323 minutes | 33406817 | | Predicted by Siyang using ReTip algorithm on June 8, 2022 | 4.8 minutes | 32390414 | | Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid | 1054.8 seconds | 40023050 | | Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid | 203.4 seconds | 40023050 | | Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid | 134.4 seconds | 40023050 | | Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid | 166.8 seconds | 40023050 | | RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 78.4 seconds | 40023050 | | Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid | 299.7 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 | 313.5 seconds | 40023050 | | HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate) | 583.5 seconds | 40023050 | | UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid | 697.1 seconds | 40023050 | | BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid | 250.6 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 | 946.0 seconds | 40023050 | | SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 185.4 seconds | 40023050 | | RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 229.1 seconds | 40023050 | | MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate | 526.4 seconds | 40023050 | | KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA | 464.7 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 | 130.9 seconds | 40023050 |
Predicted Kovats Retention IndicesUnderivatizedDerivatized| Derivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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| Dihydromorphine,1TMS,isomer #1 | CN1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2[C@@H](O[Si](C)(C)C)CC[C@H]3[C@H]1C5 | 2414.1 | Semi standard non polar | 33892256 | | Dihydromorphine,1TMS,isomer #2 | CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C)=C4O[C@H]2[C@@H](O)CC[C@H]3[C@H]1C5 | 2472.6 | Semi standard non polar | 33892256 | | Dihydromorphine,2TMS,isomer #1 | CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C)=C4O[C@H]2[C@@H](O[Si](C)(C)C)CC[C@H]3[C@H]1C5 | 2480.4 | Semi standard non polar | 33892256 | | Dihydromorphine,1TBDMS,isomer #1 | CN1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@H]3[C@H]1C5 | 2677.9 | Semi standard non polar | 33892256 | | Dihydromorphine,1TBDMS,isomer #2 | CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C(C)(C)C)=C4O[C@H]2[C@@H](O)CC[C@H]3[C@H]1C5 | 2744.8 | Semi standard non polar | 33892256 | | Dihydromorphine,2TBDMS,isomer #1 | CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C(C)(C)C)=C4O[C@H]2[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@H]3[C@H]1C5 | 2926.0 | Semi standard non polar | 33892256 |
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