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Propylnorapomorphine

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Propylnorapomorphine
Clinical data
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • (6aS)-6-propyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-10,11-diol
CAS Number
PubChemCID
ChemSpider
UNII
Chemical and physical data
FormulaC19H21NO2
Molar mass295.382 g·mol−1
3D model (JSmol)
Density1.2 g/cm3
Boiling point446 to 536 °C (835 to 997 °F)[1]
  • CCCN1CCC2=CC=CC3=C2C1CC4=C3C(=C(C=C4)O)O

N-n-Propylnorapomorphine (NPA) is anaporphine derivativedopamine agonist closely related toapomorphine.[2][3] In rodents it has been shown to producehyperactivity,stereotypy,hypothermia,antinociception, andpenile erection, among other effects.[4][5][6][7] Notably, its effects onlocomotion arebiphasic, with low doses producing inhibition andcatalepsy and high doses resulting in enhancement of activity.[8] This is likely due to preferential activation ofD2/D3autoreceptors versuspostsynapticreceptors,[9] the latter of which overcomes the former to increase postsynaptic dopaminergic signaling only with high doses.

See also

[edit]

References

[edit]
  1. ^"(6aS)-6-Propyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-10,11-diol".ChemSpider. Retrieved16 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.S2CID 23393175.
  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.S2CID 7139938.
D1-like
Agonists
PAMs
Antagonists
D2-like
Agonists
Antagonists


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