Propylnorapomorphine

Propylnorapomorphine

Systematic (IUPAC) name
(6aS)-6-propyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-10,11-diol
Clinical data
Routes of administration	Oral
Legal status	Uncontrolled
Identifiers
CAS Number	57559-68-9
ATC code	none
PubChem	CID 5311191
ChemSpider	4470712
Chemical data
Formula	C19H21NO2
Molar mass	295.38 g/mol
SMILES CCCN1CCC2=CC=CC3=C2C1CC4=C3C(=C(C=C4)O)O
Physical data
Density	1.2 g/cm^3
Boiling point	446 to 536[1] °C (835 to 997 °F)

N-n-Propylnorapomorphine (NPA) is an aporphine derivative dopamine agonist closely related to apomorphine.^[2][3] In rodents it has been shown to produce hyperactivity, stereotypy, hypothermia, antinociception, and penile erection, among other effects.^[4][5][6][7] Notably, its effects on locomotion are biphasic, with low doses producing inhibition and catalepsy and high doses resulting in enhancement of activity.^[8] This is likely due to preferential activation of D₂/D₃ autoreceptors versus postsynaptic receptors,^[9] the latter of which overcomes the former to increase postsynaptic dopaminergic signaling only with high doses.

See also

• Apomorphine

References

1. "(6aS)-6-Propyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-10,11-diol". ChemSpider. Retrieved 16 January 2016.
2. 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.
3. 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.
4. 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.
5. 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.
6. 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.
7. 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.
8. 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.
9. 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.