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Propylnorapomorphine

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Propylnorapomorphine
Clinical data

Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name (6aS)-6-propyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-10,11-diol
CAS Number	57559-68-9^Y
PubChem CID	5311191
ChemSpider	4470712
UNII	AZ9L8ZYZ3A
Chemical and physical data
Formula	C₁₉H₂₁NO₂
Molar mass	295.382 g·mol⁻¹
3D model (JSmol)	Interactive image
Density	1.2 g/cm³
Boiling point	446 to 536 °C (835 to 997 °F) ^[1]
SMILES CCCN1CCC2=CC=CC3=C2C1CC4=C3C(=C(C=C4)O)O

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.

References[edit]

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

^ 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.

^ 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.

^ 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.

^ 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.

^ 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.

^ 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.

^ 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. S2CID 23393175.

^ 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. S2CID 7139938.