Apomorphine,isanaporphinederivativeofthedibenzoquinolineclass.Apomorphineisverylipophilicandmoderatelysolubleinwaterandnormalsaline.Oxidationuponexposuretoairandlightisrapid,butcanbepreventedbytheuseofstrongacids(e.g.,hydrochloricacidorzincchloride)andantioxidants. ApomorphineactivatesD1-like(D1,D5)andD2-like(D2,D3,D4)receptors(andisthusclassifiedasanon-selectivedopamineagoNIST),SEROtoninreceptors(5HT1A,5HT2A,5HT2B,and5HT2C),andα-adrenergicreceptors(α1B,α1D,α2A,α2B,andα2C). Apomorphine’sdopaminergicactivityisduetoitspolycyclicandtertiaryaminestructures.
Apomorphinehasbeenusedinavarietyoftreatmentsrangingfromthetreatmentofaddiction(i.e.,toheroin,alcoholorcigarettes),fortreatmentoferectiledysfunctiontothetreatmentofpatientswithParkinson"sdisease.Currently,ApomorphineisusedinpatientswithadvancedParkinson"sdisease,forthetreatmentofpersistentanddisablingmotorfluctuationswhichdonotrespondtolevodopaorotherdopamineagonists,eitheronitsownorincombinationwithdeepbrainstimulation.Recently,anewandpotentiallyimportanttherapeuticroleforApomorphineinthetreatmentofAlzheimer’sdiseasehasbeensuggested;ApomorphineseemstostimulateAβ catabolisminanimalmodelsandcellculture,thusreducingtherateofA βoligomerisationandconsequentneuralcelldeath.
AdditionalInformation
| Synonyms | Hemihydrate |
|---|---|
| Product# | A-2549 |
| CAS# | 314-19-2 |
| ChemicalName | (6aR)-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-10,11-diol |
| Formula | C17H17NO2 |
| MW | 312.8 |
| Appearance | Solid |
| Purity | >98%(TLC);NMR(Conforms) |
| Solubility | Maybedissolvedinwater(20mg/ml) |
| StorageTemp | Storedesiccatedassuppliedatroomtemperatureforupto2years.Storesolutionsat-20ºCforupto1week. |
| TherapeuticArea | NeurologicalDisorders |
| Use | DopamineagonistuseinParkinson"sDisease |
| MDLNumber | MFCD00069236 |
|---|---|
| ChemACX | X1008102-2 |
| InChI | InChI=1S/C17H17NO2.ClH/c1-18-8-7-10-3-2-4-12-15(10)13(18)9-11-5-6-14(19)17(20)16(11)12;/h4-6,13,19-20H,7-9H2,1H3;1H/t13-;/m1./s1 |
| SMILES | CN1CCc2cccc-3c2[C@H]1Cc4c3c(c(cc4)O)O.Cl |
