Propylnorapomorphine

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = (6aS)-6-propyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-10,11-diol

| image = Propylnorapomorphine.svg

| tradename =

| pregnancy_category =

| legal_status = Uncontrolled

| routes_of_administration = Oral

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 57559-68-9

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = AZ9L8ZYZ3A

| ATC_prefix = none

| ATC_suffix =

| PubChem = 5311191

| ChemSpiderID = 4470712

| C=19 | H=21 | N=1 | O=2

| smiles = CCCN1CCC2=CC=CC3=C2C1CC4=C3C(=C(C=C4)O)O

| density = 1.2

| boiling_point = 446

| boiling_high = 536

| boiling_notes = {{cite web|title=(6aS)-6-Propyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-10,11-diol|url=http://www.chemspider.com/Chemical-Structure.4470712.html|website=ChemSpider|access-date=16 January 2016}}

}}

N-n-Propylnorapomorphine (NPA) is an aporphine derivative dopamine agonist closely related to apomorphine.{{cite journal |vauthors=Miller RJ, Kelly PH, Neumeyer JL | title = Aporphines. 15. Action of aporphine alkaloids on dopaminergic mechanisms in rat brain | journal = European Journal of Pharmacology | volume = 35 | issue = 1 | pages = 77–83 |date=January 1976 | pmid = 943290 | doi = 10.1016/0014-2999(76)90302-2}}{{cite journal |vauthors=Creese I, Padgett L, Fazzini E, Lopez F | title = 3H-N-n-propylnorapomorphine: a novel agonist ligand for central dopamine receptors | journal = European Journal of Pharmacology | volume = 56 | issue = 4 | pages = 411–2 |date=July 1979 | pmid = 477735 | doi = 10.1016/0014-2999(79)90274-7}} In rodents it has been shown to produce hyperactivity, stereotypy, hypothermia, antinociception, and penile erection, among other effects.{{cite journal |vauthors=Menon MK, Clark WG, Neumeyer JL | title = Comparison of the dopaminergic effects of apomorphine and (−)-N-n-propylnorapomorphine | journal = European Journal of Pharmacology | volume = 52 | issue = 1 | pages = 1–9 |date=November 1978 | pmid = 569056 | doi = 10.1016/0014-2999(78)90015-8}}{{cite journal |vauthors=Riffee WH, Wilcox RE, Smith RV | title = Stereotypic and hypothermic effects of apomorphine and N-n-propylnorapomorphine in mice | journal = European Journal of Pharmacology | volume = 54 | issue = 3 | pages = 273–7 |date=March 1979 | pmid = 570924 | doi = 10.1016/0014-2999(79)90086-4}}{{cite journal |vauthors=Neumeyer JL, Reinhard JF, Dafeldecker WP, etal | title = Aporphines. 14 Dopaminergic and antinociceptive activity of aporphine derivatives. Synthesis of 10-hydroxyaporphines and 10-hydroxy-N-n-propylnoraporphine | journal = Journal of Medicinal Chemistry | volume = 19 | issue = 1 | pages = 25–9 |date=January 1976 | pmid = 942751 | doi = 10.1021/jm00223a006}}{{cite journal |vauthors=Benassi-Benelli A, Ferrari F, Quarantotti BP | title = Penile erection induced by apomorphine and N-n-propyl-norapomorphine in rats | journal = Archives Internationales de Pharmacodynamie et de Thérapie | volume = 242 | issue = 2 | pages = 241–7 |date=December 1979 | pmid = 44457 }} Notably, its effects on locomotion are biphasic, with low doses producing inhibition and catalepsy and high doses resulting in enhancement of activity.{{cite journal |vauthors=Campbell A, Baldessarini RJ, Ram VJ, Neumeyer JL | title = Behavioral effects of (-)10,11-methylenedioxy-N-n-propylnoraporphine, an orally effective long-acting agent active at central dopamine receptors, and analogous aporphines | journal = Neuropharmacology | volume = 21 | issue = 10 | pages = 953–61 |date=October 1982 | pmid = 6890636 | doi = 10.1016/0028-3908(82)90106-X| s2cid = 23393175 }} This is likely due to preferential activation of D₂/D₃ autoreceptors versus postsynaptic receptors,{{cite journal |vauthors=Argiolas A, Mereu G, Serra G, Melis MR, Fadda F, Gessa GL | title = N-n-propyl-norapomorphine: an extremely potent stimulant of dopamine autoreceptors | journal = Brain Research | volume = 231 | issue = 1 | pages = 109–16 |date=January 1982 | pmid = 6799148 | doi = 10.1016/0006-8993(82)90011-7| s2cid = 7139938 }} the latter of which overcomes the former to increase postsynaptic dopaminergic signaling only with high doses.