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apomorphine

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EntityQ269111· pop 30· linked from 965 articles

apomorphine

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Also 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

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)

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~18 min read

Article

19 sections
Contents
  • 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.

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