Structure via PubChem · Public domain (PubChem)
apomorphine
Sign in to saveAlso known as Apokyn®, Ixense®, Uprima®, R-(-)-apomorphine, (R)-5,6,6a,7-tetrahydro-6-methyl-4H-dibenzo[de,g]quinoline-10,11-diol, (-)-10,11-dihydroxyaporphine, (6aR)-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-10,11-diol
Apomorphine, sold under the brand name Apokyn among others, is a type of aporphine that functions as a non-selective dopamine agonist which activates both D2-like and, to a much lesser extent, D1-like receptors. It also acts as an antagonist of 5-HT2 and α-adrenergic receptors with high affinity. The compound is an alkaloid belonging to nymphaea caerulea, or blue lotus, but is also historically known as a morphine decomposition product made by boiling morphine with concentrated acid, hence the -morphine suffix. Contrary to its name, apomorphine does not actually contain morphine or its skeleto
Chemical data
- Formula
- C17H17NO2
- Molecular weight
- 267.32 g/mol
- IUPAC name
- (6aR)-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-10,11-diol
- SMILES
- CN1CCC2=C3[C@H]1CC4=C(C3=CC=C2)C(=C(C=C4)O)O
- InChIKey
- VMWNQDUVQKEIOC-CYBMUJFWSA-N
- XLogP
- 2.3
- Polar surface area
- 43.7 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
12,666 papers- Apomorphine-subcutaneous--Bertek/Britannia.Drugs in R&D · 2004
- [Apomorphine and frontal dysfunction in Parkinson's disease].Revista de neurologia · 2022
- Sublingual apomorphine in treatment of Parkinson's disease: a review.The International journal of neuroscience · 2024
- An evaluation of subcutaneous apomorphine for the treatment of Parkinson's disease.Expert opinion on pharmacotherapy · 2020
- [Apomorphine].Neurologia (Barcelona, Spain) · 1995
via PubMed
Wikidata facts
- Mass
- 267.125929
Show 5 more facts
- chemical formula
- C₁₇H₁₇NO₂
- Commons category
- Apomorphine
- canonical SMILES
- CN1CCC2=CC=CC3=C2C1CC4=C3C(=C(C=C4)O)O
- isomeric SMILES
- CN1CCC2=CC=CC3=C2[C@H]1CC4=C3C(=C(C=C4)O)O
- defined daily dose
- 2
Sources (6)
via Wikidata · CC0
~18 min read
Article
19 sectionsContents
- Medical uses
- Parkinson's disease
- Contraindications
- Side effects
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- Chemistry
- Properties
- Synthesis
- Historical medical uses
- Treatment of alcoholism
- Aversion therapy
- Opioid addiction
- Alternative administration routes
- Veterinary use
- Related compounds
- See also
- References
Apomorphine, sold under the brand name Apokyn among others, is a type of aporphine that functions as a non-selective dopamine agonist which activates both D2-like and, to a much lesser extent, D1-like receptors. It also acts as an antagonist of 5-HT2 and α-adrenergic receptors with high affinity. The compound is an alkaloid belonging to nymphaea caerulea, or blue lotus, but is also historically known as a morphine decomposition product made by boiling morphine with concentrated acid, hence the -morphine suffix. Contrary to its name, apomorphine does not actually contain morphine or its skeleton, nor does it bind to opioid receptors. The apo- prefix relates to it being a morphine derivative ("[comes] from morphine").
Historically, apomorphine has been tried for a variety of uses, including as a way to relieve anxiety and craving in alcoholics, an emetic (to induce vomiting), for treating stereotypies (repeated behaviour) in farmyard animals, and more recently in treating erectile dysfunction. Currently, apomorphine is used in the treatment of Parkinson's disease. It is a potent emetic and should not be administered without an antiemetic such as domperidone. The emetic properties of apomorphine are exploited in veterinary medicine to induce therapeutic emesis in canines that have recently ingested toxic or foreign substances.