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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 15:16:50 UTC |
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Update Date | 2020-02-26 21:40:27 UTC |
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HMDB ID | HMDB0014852 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Apomorphine |
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Description | Apomorphine, also known as uprima or apomorfin, belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. Apomorphine is a drug which is used for the acute, intermittent treatment of hypomobility, off episodes (end-of-dose wearing off and unpredictable on/off episodes) associated with advanced parkinson's disease. Apomorphine is a very strong basic compound (based on its pKa). Apomorphine is a potentially toxic compound. In particular, apomorphine attenuates the motor deficits induced by lesions in the ascending nigrostriatal dopaminergic pathway with the neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) in primates. Apomorphine has been shown to improve motor function in an animal model of Parkinson's disease. It is a powerful emetic and has been used for that effect in acute poisoning. In higher doses it is a highly effective emetic. |
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Structure | |
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Synonyms | Value | Source |
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(-)-10,11-Dihydroxyaporphine | ChEBI | (6AR)-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-10,11-diol | ChEBI | (R)-5,6,6a,7-Tetrahydro-6-methyl-4H-dibenzo[de,g]quinoline-10,11-diol | ChEBI | Apomorphin | ChEBI | R-(-)-Apomorphine | ChEBI | Uprima | Kegg | Apomorfin | HMDB | Apomorphine hydrochloride hemihydrate | HMDB | Apomorphinium chloride hemihydrate | HMDB | Apormorphine | HMDB | L-Apomorphine | HMDB | VR-040 | HMDB | VR-400 | HMDB | VR004 | HMDB | Anhydrous apomorphine hydrochloride | HMDB | Apomorphin-teclapharm | HMDB | Britannia brand OF apomorphine hydrochloride | HMDB | Hemihydrate apomorphine hydrochloride | HMDB | Apomorphine hydrochloride, hemihydrate | HMDB | Britaject | HMDB | Chloride, apomorphine | HMDB | Hydrochloride, apomorphine | HMDB | Aguettant brand OF apomorphine hydrochloride | HMDB | Apokinon | HMDB | Apomorphine hydrochloride, anhydrous | HMDB | Hydrochloride, anhydrous apomorphine | HMDB | Teclapharm brand OF apomorphine hydrochloride | HMDB | Anhydrous, apomorphine hydrochloride | HMDB | Apomorphin teclapharm | HMDB | ApomorphinTeclapharm | HMDB | Apomorphine chloride | HMDB | Apomorphine hydrochloride | HMDB | Apomorphine hydrochloride anhydrous | HMDB | Hydrochloride anhydrous, apomorphine | HMDB | Hydrochloride, hemihydrate apomorphine | HMDB |
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Chemical Formula | C17H17NO2 |
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Average Molecular Weight | 267.3224 |
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Monoisotopic Molecular Weight | 267.125928793 |
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IUPAC Name | (9R)-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),3,5,13(17),14-hexaene-3,4-diol |
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Traditional Name | apomorphine |
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CAS Registry Number | 41372-20-7 |
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SMILES | [H][C@]12CC3=C(C(O)=C(O)C=C3)C3=CC=CC(CCN1C)=C23 |
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InChI Identifier | InChI=1S/C17H17NO2/c1-18-8-7-10-3-2-4-12-15(10)13(18)9-11-5-6-14(19)17(20)16(11)12/h2-6,13,19-20H,7-9H2,1H3/t13-/m1/s1 |
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InChI Key | VMWNQDUVQKEIOC-CYBMUJFWSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. |
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Kingdom | Organic compounds |
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Super Class | Alkaloids and derivatives |
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Class | Aporphines |
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Sub Class | Not Available |
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Direct Parent | Aporphines |
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Alternative Parents | |
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Substituents | - Aporphine
- Benzoquinoline
- Phenanthrene
- 2-naphthol
- 1-naphthol
- Naphthalene
- Quinoline
- Tetrahydroisoquinoline
- 1-hydroxy-2-unsubstituted benzenoid
- 1-hydroxy-4-unsubstituted benzenoid
- Aralkylamine
- Benzenoid
- Tertiary aliphatic amine
- Tertiary amine
- Organoheterocyclic compound
- Azacycle
- Organic nitrogen compound
- Organopnictogen compound
- Organooxygen compound
- Organonitrogen compound
- Organic oxygen compound
- Amine
- Hydrocarbon derivative
- 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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Disposition | Route of exposure: Biological location: |
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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 | 0.51 g/L | Not Available | LogP | 3.1 | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0gb9-0190000000-4a508d96ec3f544ad0a5 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive | splash10-01vt-1119000000-110790047aaa5266ec7d | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-014r-0090000000-29608efdadd8efd375a6 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-000i-0090000000-052772c02bbf103a3ef5 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-00kr-0290000000-1e831a8078d43cfbdb51 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-000i-0090000000-49baaafc781fbd1a40ea | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-000i-0090000000-b2abd157ce4880c73d0b | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-000i-0090000000-b747e9bb748f801c3f50 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-000i-0090000000-1a55345a571167f3fca6 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-0090000000-0329e43d2073db5426bb | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-014r-0190000000-4dc4f5ea615d9b0a78e2 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05xu-1950000000-298a2d8a85a241732677 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0090000000-8dcf24a32f1f7baba7c2 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-014i-0090000000-734acff31070eb2a5a84 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0udl-2190000000-5a6e0c712dad2d12eaa9 | Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00714 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00714 | | details |
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Abnormal Concentrations |
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| Not Available |
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Predicted Concentrations |
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Blood | 0.000 uM | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities | Blood | 0.000 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB00714 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 5783 |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Apomorphine |
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METLIN ID | Not Available |
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PubChem Compound | 6005 |
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PDB ID | Not Available |
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ChEBI ID | 48538 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Corsini GU, Del Zompo M, Gessa GL, Mangoni A: Therapeutic efficacy of apomorphine combined with an extracerebral inhibitor of dopamine receptors in Parkinson's disease. Lancet. 1979 May 5;1(8123):954-6. [PubMed:87620 ]
- Cotzias GC, Papavasiliou PS, Fehling C, Kaufman B, Mena I: Similarities between neurologic effects of L-dopa and of apomorphine. N Engl J Med. 1970 Jan 1;282(1):31-3. [PubMed:4901383 ]
- Chaudhuri KR, Clough C: Subcutaneous apomorphine in Parkinson's disease. BMJ. 1998 Feb 28;316(7132):641. [PubMed:9522772 ]
- SCHWAB RS, AMADOR LV, LETTVIN JY: Apomorphine in Parkinson's disease. Trans Am Neurol Assoc. 1951;56:251-3. [PubMed:14913646 ]
- Matsumoto K, Yoshida M, Andersson KE, Hedlund P: Effects in vitro and in vivo by apomorphine in the rat corpus cavernosum. Br J Pharmacol. 2005 Sep;146(2):259-67. [PubMed:16025145 ]
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