Apomorphine

Apomorphine
Clinical data
Trade names	Apokyn, Kynmobi
AHFS/Drugs.com	Monograph
MedlinePlus	a604020
License data	US DailyMed: Apomorphine;
Pregnancy; category	AU: B3; ;
Routes of; administration	Subcutaneous injection (SQ), sublingual
ATC code	G04BE07 (WHO) N04BC07 (WHO) QV03AB95 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	100% following injection
Protein binding	~50%
Metabolism	Liver, phase II
Onset of action	10–20 min
Elimination half-life	40 minutes
Duration of action	60–90 min
Excretion	Liver
Identifiers
	IUPAC name (6aR)-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-10,11-diol;
CAS Number	58-00-4 ; HCl: 41372-20-7 ;
PubChem CID	6005;
IUPHAR/BPS	33;
DrugBank	DB00714 ;
ChemSpider	5783 ;
UNII	N21FAR7B4S; HCl: F39049Y068 ;
KEGG	D07460 ;
ChEBI	CHEBI:48538 ;
ChEMBL	ChEMBL53 ;
CompTox Dashboard (EPA)	DTXSID8022614 ;
ECHA InfoCard	100.000.327
Chemical and physical data
Formula	C17H17NO2
Molar mass	267.328 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES OC1=C(O)C(C2=CC=CC3=C2[C@@H](C4)N(C)CC3)=C4C=C1;
	InChI 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 ; Key:VMWNQDUVQKEIOC-CYBMUJFWSA-N ;
Data page
	Apomorphine (data page)
	(what is this?) (verify)

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.^[1] 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.^[2] There is, however, no clinical evidence that apomorphine is an effective and safe treatment regimen for opiate addiction.^[3]

^ 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.
^ 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.
^ 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.

[pmid12388666-1] 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.

[2] 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.

[Dent_1949-3] 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.

[1]

[2]

[3]