Apomorphine

Apomorphine
Clinical data
Trade namesApokyn, Kynmobi
AHFS/Drugs.comMonograph
MedlinePlusa604020
License data
Pregnancy
category
  • AU: B3
Routes of
administration
Subcutaneous injection (SQ), sublingual
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability100% following injection
Protein binding~50%
MetabolismLiver, phase II
Onset of action10–20 min
Elimination half-life40 minutes
Duration of action60–90 min
ExcretionLiver
Identifiers
  • (6aR)-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-10,11-diol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.327 Edit this at Wikidata
Chemical and physical data
FormulaC17H17NO2
Molar mass267.328 g·mol−1
3D model (JSmol)
  • OC1=C(O)C(C2=CC=CC3=C2[C@@H](C4)N(C)CC3)=C4C=C1
  • 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 checkY
  • Key:VMWNQDUVQKEIOC-CYBMUJFWSA-N checkY
Data page
Apomorphine (data page)
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Apomorphine, sold under the brand name Apokyn among others, is a type of aporphine having activity as a non-selective dopamine agonist which activates both D2-like and, to a much lesser extent, D1-like receptors.[2] It also acts as an antagonist of 5-HT2 and α-adrenergic receptors with high affinity. The compound is historically 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.

Apomorphine was also used as a private treatment of heroin addiction, a purpose for which it was championed by the author William S. Burroughs. Burroughs and others claimed that it was a "metabolic regulator" with a restorative dimension to a damaged or dysfunctional dopaminergic system. Despite anecdotal evidence that this offers a plausible route to an abstinence-based mode, no clinical trials have ever tested this hypothesis. A recent study indicates that apomorphine might be a suitable marker for assessing central dopamine system alterations associated with chronic heroin consumption.[3] There is, however, no clinical evidence that apomorphine is an effective and safe treatment regimen for opiate addiction.[4]

  1. ^ "Movapo Pod (Stada Pharmaceuticals Australia Pty Ltd)". Therapeutic Goods Administration (TGA). 13 September 2024. Retrieved 15 September 2024.
  2. ^ Millan MJ, Maiofiss L, Cussac D, Audinot V, Boutin JA, Newman-Tancredi A (November 2002). "Differential actions of antiparkinson agents at multiple classes of monoaminergic receptor. I. A multivariate analysis of the binding profiles of 14 drugs at 21 native and cloned human receptor subtypes". The Journal of Pharmacology and Experimental Therapeutics. 303 (2): 791–804. doi:10.1124/jpet.102.039867. PMID 12388666. S2CID 6200455.
  3. ^ Guardia J, Casas M, Prat G, Trujols J, Segura L, Sánchez Turet M (October 2002). "The apomorphine test: a biological marker for heroin dependence disorder?". Addiction Biology. 7 (4): 421–426. doi:10.1080/1355621021000006206. PMID 14578019. S2CID 32386793.
  4. ^ Dent JY (1949). "Apomorphine Treatment of Addiction". British Journal of Addiction to Alcohol & Other Drugs. 46 (1): 15–28. doi:10.1111/j.1360-0443.1949.tb04502.x.