Propylnorapomorphine

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Propylnorapomorphine
Propylnorapomorphine.svg
Systematic (IUPAC) name
(6aS)-6-propyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-10,11-diol
Clinical data
Legal status
  • Uncontrolled
Routes Oral
Identifiers
CAS number 57559-68-9
ATC code None
PubChem CID 5311191
ChemSpider 4470712
Chemical data
Formula C19H21NO2 
Mol. mass 295.38 g/mol

N-n-Propylnorapomorphine (NPA) is an aporphine derivative dopamine agonist closely related to apomorphine.[1][2] In rodents it has been shown to produce hyperactivity, stereotypy, hypothermia, antinociception, and penile erection, among other effects.[3][4][5][6] Notably, its effects on locomotion are biphasic[disambiguation needed], with low doses producing inhibition and catalepsy and high doses resulting in enhancement of activity.[7] This is likely due to preferential activation of D2/D3 autoreceptors versus postsynaptic receptors,[8] the latter of which overpowers the former only with high doses.

See also[edit]

References[edit]

  1. ^ Miller RJ, Kelly PH, Neumeyer JL (January 1976). "Aporphines. 15. Action of aporphine alkaloids on dopaminergic mechanisms in rat brain". European Journal of Pharmacology 35 (1): 77–83. doi:10.1016/0014-2999(76)90302-2. PMID 943290. 
  2. ^ Creese I, Padgett L, Fazzini E, Lopez F (July 1979). "3H-N-n-propylnorapomorphine: a novel agonist ligand for central dopamine receptors". European Journal of Pharmacology 56 (4): 411–2. doi:10.1016/0014-2999(79)90274-7. PMID 477735. 
  3. ^ Menon MK, Clark WG, Neumeyer JL (November 1978). "Comparison of the dopaminergic effects of apomorphine and (-)-N-n-propylnorapomorphine". European Journal of Pharmacology 52 (1): 1–9. doi:10.1016/0014-2999(78)90015-8. PMID 569056. 
  4. ^ Riffee WH, Wilcox RE, Smith RV (March 1979). "Stereotypic and hypothermic effects of apomorphine and N-n-propylnorapomorphine in mice". European Journal of Pharmacology 54 (3): 273–7. doi:10.1016/0014-2999(79)90086-4. PMID 570924. 
  5. ^ Neumeyer JL, Reinhard JF, Dafeldecker WP, et al. (January 1976). "Aporphines. 14 Dopaminergic and antinociceptive activity of aporphine derivatives. Synthesis of 10-hydroxyaporphines and 10-hydroxy-N-n-propylnoraporphine". Journal of Medicinal Chemistry 19 (1): 25–9. doi:10.1021/jm00223a006. PMID 942751. 
  6. ^ Benassi-Benelli A, Ferrari F, Quarantotti BP (December 1979). "Penile erection induced by apomorphine and N-n-propyl-norapomorphine in rats". Archives Internationales De Pharmacodynamie Et De Thérapie 242 (2): 241–7. PMID 44457. 
  7. ^ Campbell A, Baldessarini RJ, Ram VJ, Neumeyer JL (October 1982). "Behavioral effects of (-)10,11-methylenedioxy-N-n-propylnoraporphine, an orally effective long-acting agent active at central dopamine receptors, and analogous aporphines". Neuropharmacology 21 (10): 953–61. doi:10.1016/0028-3908(82)90106-X. PMID 6890636. 
  8. ^ Argiolas A, Mereu G, Serra G, Melis MR, Fadda F, Gessa GL (January 1982). "N-n-propyl-norapomorphine: an extremely potent stimulant of dopamine autoreceptors". Brain Research 231 (1): 109–16. doi:10.1016/0006-8993(82)90011-7. PMID 6799148.