| Record Information |
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| Version | 5.0 |
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| Status | Expected but not Quantified |
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| Creation Date | 2012-09-13 11:50:03 UTC |
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| Update Date | 2021-09-14 15:19:57 UTC |
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| HMDB ID | HMDB0041959 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Normorphine |
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| Description | Normorphine, also known as desmethylmorphine, 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. The compound has relatively little opioid activity in its own right, but is a useful intermediate which can be used to produce both opioid antagonists such as nalorphine, and also potent opioid agonists such as N-phenethylnormorphine. Normorphine is a very strong basic compound (based on its pKa). Its formation from morphine is catalyzed by the liver enzymes CYP3A4 and CYP2C8. Normorphine is a controlled substance listed under the Single Convention On Narcotic Drugs 1961 and the laws in various states implementing it; for example, in the United States, it is a Schedule I Narcotic controlled substance, with an ACSCN of 9313 and an annual aggregate manufacturing quota of 18 grams in 2014, unchanged from the prior year. Normorphine is an opiate analogue, the N-demethylated derivative of morphine, that was first described in the 1950s when a large group of N-substituted morphine analogues were characterized for activity. |
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| Structure | [H][C@@]12OC3=C4C(C[C@@]5([H])NCC[C@@]14[C@@]5([H])C=C[C@@H]2O)=CC=C3O InChI=1S/C16H17NO3/c18-11-3-1-8-7-10-9-2-4-12(19)15-16(9,5-6-17-10)13(8)14(11)20-15/h1-4,9-10,12,15,17-19H,5-7H2/t9-,10+,12-,15-,16-/m0/s1 |
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| Synonyms | | Value | Source |
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| Desmethylmorphine | HMDB | | Normorphine perchlorate | HMDB | | N-Demethylmorphine | HMDB | | (5alpha,6alpha)-7,8-Didehydro-4,5-epoxymorphinan-3,6-diol hydrochloride | HMDB | | 4,5-Epoxy-3,6-dihydroxymorphin-7-ene | HMDB | | Normorphine hydrochloride | HMDB | | Normorphine sulfamate | HMDB | | (-)-Normorphine | HMDB | | (5alpha,6alpha)-7,8-Didehydro-4,5-epoxymorphinan-3,6-diol | HMDB | | (5Α,6α)-7,8-didehydro-4,5-epoxymorphinan-3,6-diol | HMDB | | 4,5-Epoxy-3,6-dihydromorphin-7-ene | HMDB | | Demethylmorphine | HMDB | | N-Normorphine | HMDB | | Normorphine | HMDB |
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| Chemical Formula | C16H17NO3 |
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| Average Molecular Weight | 271.316 |
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| Monoisotopic Molecular Weight | 271.120843411 |
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| IUPAC Name | (1S,5R,13R,14S,17R)-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7,9,11(18),15-tetraene-10,14-diol |
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| Traditional Name | (1S,5R,13R,14S,17R)-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7,9,11(18),15-tetraene-10,14-diol |
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| CAS Registry Number | 466-97-7 |
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| SMILES | [H][C@@]12OC3=C4C(C[C@@]5([H])NCC[C@@]14[C@@]5([H])C=C[C@@H]2O)=CC=C3O |
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| InChI Identifier | InChI=1S/C16H17NO3/c18-11-3-1-8-7-10-9-2-4-12(19)15-16(9,5-6-17-10)13(8)14(11)20-15/h1-4,9-10,12,15,17-19H,5-7H2/t9-,10+,12-,15-,16-/m0/s1 |
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| InChI Key | ONBWJWYUHXVEJS-ZTYRTETDSA-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
- Secondary alcohol
- Secondary aliphatic amine
- Ether
- Oxacycle
- Secondary amine
- Azacycle
- Organoheterocyclic compound
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Amine
- Alcohol
- Organic nitrogen 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 | Not Available |
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| Disposition | |
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| Process | |
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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 | 273 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | -0.17 | Not Available |
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| Experimental Chromatographic Properties | Not Available |
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| Predicted Molecular Properties | | Show more...
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| Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized| Derivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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| Normorphine,1TMS,isomer #1 | C[Si](C)(C)O[C@H]1C=C[C@H]2[C@H]3CC4=CC=C(O)C5=C4[C@@]2(CCN3)[C@H]1O5 | 2467.3 | Semi standard non polar | 33892256 | | Normorphine,1TMS,isomer #2 | C[Si](C)(C)OC1=CC=C2C[C@H]3NCC[C@]45C2=C1O[C@H]4[C@@H](O)C=C[C@@H]35 | 2503.2 | Semi standard non polar | 33892256 | | Normorphine,1TMS,isomer #3 | C[Si](C)(C)N1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2[C@@H](O)C=C[C@H]3[C@H]1C5 | 2500.7 | Semi standard non polar | 33892256 | | Normorphine,2TMS,isomer #1 | C[Si](C)(C)OC1=CC=C2C[C@H]3NCC[C@]45C2=C1O[C@H]4[C@@H](O[Si](C)(C)C)C=C[C@@H]35 | 2507.3 | Semi standard non polar | 33892256 | | Normorphine,2TMS,isomer #2 | C[Si](C)(C)O[C@H]1C=C[C@H]2[C@H]3CC4=CC=C(O)C5=C4[C@@]2(CCN3[Si](C)(C)C)[C@H]1O5 | 2500.5 | Semi standard non polar | 33892256 | | Normorphine,2TMS,isomer #3 | C[Si](C)(C)OC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C | 2507.8 | Semi standard non polar | 33892256 | | Normorphine,3TMS,isomer #1 | C[Si](C)(C)OC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C | 2537.1 | Semi standard non polar | 33892256 | | Normorphine,3TMS,isomer #1 | C[Si](C)(C)OC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[Si](C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C | 2646.5 | Standard non polar | 33892256 | | Normorphine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@H]2[C@H]3CC4=CC=C(O)C5=C4[C@@]2(CCN3)[C@H]1O5 | 2746.0 | Semi standard non polar | 33892256 | | Normorphine,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=C2C[C@H]3NCC[C@]45C2=C1O[C@H]4[C@@H](O)C=C[C@@H]35 | 2775.7 | Semi standard non polar | 33892256 | | Normorphine,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2[C@@H](O)C=C[C@H]3[C@H]1C5 | 2722.9 | Semi standard non polar | 33892256 | | Normorphine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C2C[C@H]3NCC[C@]45C2=C1O[C@H]4[C@@H](O[Si](C)(C)C(C)(C)C)C=C[C@@H]35 | 2990.2 | Semi standard non polar | 33892256 | | Normorphine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)O[C@H]1C=C[C@H]2[C@H]3CC4=CC=C(O)C5=C4[C@@]2(CCN3[Si](C)(C)C(C)(C)C)[C@H]1O5 | 2957.8 | Semi standard non polar | 33892256 | | Normorphine,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C(C)(C)C | 2960.0 | Semi standard non polar | 33892256 | | Normorphine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C(C)(C)C | 3235.5 | Semi standard non polar | 33892256 | | Normorphine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C2C[C@@H]3[C@@H]4C=C[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]5OC1=C2[C@@]54CCN3[Si](C)(C)C(C)(C)C | 3323.7 | Standard non polar | 33892256 |
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