A-77636

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A-77636
Stereo, Kekulé skeletal formula of A-77636
Names
IUPAC name
(1R,3S)-3-(1-Adamantyl)-1-(aminomethyl)-3,4-dihydro-1H-isochromene-5,6-diol[1]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C20H27NO3/c21-10-17-14-1-2-16(22)19(23)15(14)6-18(24-17)20-7-11-3-12(8-20)5-13(4-11)9-20/h1-2,11-13,17-18,22-23H,3-10,21H2/t11?,12?,13?,17-,18-,20?/m0/s1 checkY
    Key: QLJOSZATCBCBDR-DFKUFRTHSA-N checkY
  • InChI=1/C20H27NO3/c21-10-17-14-1-2-16(22)19(23)15(14)6-18(24-17)20-7-11-3-12(8-20)5-13(4-11)9-20/h1-2,11-13,17-18,22-23H,3-10,21H2/t11?,12?,13?,17-,18-,20?/m0/s1
    Key: QLJOSZATCBCBDR-DFKUFRTHBM
  • Oc1ccc2c(c1O)C[C@H](O[C@H]2CN)C35CC4CC(C3)CC(C4)C5
Properties
C20H27NO3
Molar mass 329.440 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

A-77636 is a synthetic drug which acts as a selective D1 receptor full agonist.[2] It has nootropic, anorectic, rewarding and antiparkinsonian effects in animal studies,[3][4][5][6][7] but its high potency and long duration of action causes D1 receptor downregulation and tachyphylaxis,[8][9][10] and unlike other D1 full agonists such as SKF-82,958, it does not produce place preference in animals.[11] A-77636 partially substituted for cocaine in animal studies, and has been suggested for use as a possible substitute drug in treating addiction,[12] but it is better known for its use in studying the role of D1 receptors in the brain.[13][14][15]

References

  1. ^ CID 6603703 from PubChem
  2. ^ "A-77636: a potent and selective dopamine D1 receptor agonist with antiparkinsonian activity in marmosets". European Journal of Pharmacology. 229 (2–3): 203–9. December 1992. doi:10.1016/0014-2999(92)90556-J. PMID 1362704. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
  3. ^ "Repeated D1 receptor agonist treatment blocks cocaine-induced locomotor activity and c-fos expression". Brain Research. 637 (1–2): 342–4. February 1994. doi:10.1016/0006-8993(94)91258-0. PMID 7910104. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
  4. ^ "The effects of systemic and intracerebral injections of D1 and D2 agonists on brain stimulation reward". Brain Research. 651 (1–2): 283–92. July 1994. doi:10.1016/0006-8993(94)90708-0. PMID 7922577. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
  5. ^ "Potential therapeutic use of the selective dopamine D1 receptor agonist, A-86929: an acute study in parkinsonian levodopa-primed monkeys". Neurology. 49 (2): 421–6. August 1997. doi:10.1212/wnl.49.2.421. PMID 9270571. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
  6. ^ "Dose-dependent effects of the dopamine D1 receptor agonists A77636 or SKF81297 on spatial working memory in aged monkeys". The Journal of Pharmacology and Experimental Therapeutics. 283 (1): 183–9. October 1997. PMID 9336323. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
  7. ^ "The anorectic effect of the selective dopamine D1-receptor agonist A-77636 determined by meal pattern analysis in free-feeding rats". European Journal of Pharmacology. 532 (3): 253–7. February 2006. doi:10.1016/j.ejphar.2005.11.046. PMID 16478622. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
  8. ^ "Persistent activation of the dopamine D1 receptor contributes to prolonged receptor desensitization: studies with A-77636". The Journal of Pharmacology and Experimental Therapeutics. 276 (3): 1022–9. March 1996. PMID 8786531. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
  9. ^ "Negative feedback regulation of nigrostriatal dopamine release: mediation by striatal D1 receptors". The Journal of Pharmacology and Experimental Therapeutics. 311 (1): 342–8. October 2004. doi:10.1124/jpet.104.067991. PMID 15175419. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
  10. ^ "Functional selectivity of dopamine D1 receptor agonists in regulating the fate of internalized receptors". Neuropharmacology. 52 (2): 562–75. February 2007. doi:10.1016/j.neuropharm.2006.08.028. PMC 1855220. PMID 17067639. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
  11. ^ "Differential ability of D1 and D2 dopamine receptor agonists to induce and modulate expression and reinstatement of cocaine place preference in rats". Psychopharmacology. 191 (3): 719–30. April 2007. doi:10.1007/s00213-006-0473-5. PMID 16835769. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
  12. ^ "Comparison of interactions of D1-like agonists, SKF 81297, SKF 82958 and A-77636, with cocaine: locomotor activity and drug discrimination studies in rodents". Psychopharmacology. 159 (2): 145–53. January 2002. doi:10.1007/s002130100896. PMID 11862342. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
  13. ^ "Nonstriatal dopamine D1 receptors regulate striatal acetylcholine release in vivo". The Journal of Pharmacology and Experimental Therapeutics. 281 (1): 360–8. April 1997. PMID 9103518. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
  14. ^ "Effects of full D1 dopamine receptor agonists on firing rates in the globus pallidus and substantia nigra pars compacta in vivo: tests for D1 receptor selectivity and comparisons to the partial agonist SKF 38393". The Journal of Pharmacology and Experimental Therapeutics. 286 (1): 272–81. July 1998. PMID 9655869. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
  15. ^ "Dopaminergic regulation of orexin neurons". The European Journal of Neuroscience. 21 (11): 2993–3001. June 2005. doi:10.1111/j.1460-9568.2005.04121.x. PMID 15978010. {{cite journal}}: Cite uses deprecated parameter |authors= (help)


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