Chemistry:A-68930

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A-68930
Stereo, Kekulé skeletal formula of A-68930
Names
Preferred IUPAC name
(1R,3S)-1-(Aminomethyl)-3-phenyl-3,4-dihydro-1H-2-benzopyran-5,6-diol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
MeSH A+68930
UNII
Properties
C16H17NO3
Molar mass 271.316 g·mol−1
log P 1.175
Acidity (pKa) 9.491
Basicity (pKb) 4.506
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is ☑Y☒N ?)
Infobox references

A-68930 is a synthetic compound that acts as a selective dopamine receptor D1 agonist.[1][2] It is orally active and has antidepressant and anorectic effects in animals, producing wakefulness and tachycardia,[3][4][5][6] but without stimulant effects, instead producing sedation.[7][8] The difference in effects between A-68930 and other D1 agonists such as SKF-82958 may be due to their differing effects on the related D5 receptor.[9]

References

  1. "(1R,3S)-1-(aminomethyl)-3,4-dihydro-5,6-dihydroxy-3-phenyl-1H-2-benzopyran: a potent and selective D1 agonist". Journal of Medicinal Chemistry 33 (11): 2948–50. November 1990. doi:10.1021/jm00173a005. PMID 1977907. 
  2. "A68930: a potent agonist selective for the dopamine D1 receptor". European Journal of Pharmacology 199 (2): 209–19. June 1991. doi:10.1016/0014-2999(91)90459-4. PMID 1683288. 
  3. "The dopamine D1 receptor agonists, A68930 and SKF 38393, induce arousal and suppress REM sleep in the rat". European Journal of Pharmacology 235 (1): 83–7. April 1993. doi:10.1016/0014-2999(93)90823-Z. PMID 8100197. 
  4. "Cardiovascular and renal hemodynamic effects of A-68930 in the conscious dog: a comparison with fenoldopam". The Journal of Pharmacology and Experimental Therapeutics 268 (2): 565–70. February 1994. PMID 7906731. 
  5. "A-68930, a novel, potent dopamine D1 receptor agonist: a microstructural analysis of its effects on feeding and other behaviour in the rat". Behavioural Pharmacology 5 (2): 210–218. April 1994. doi:10.1097/00008877-199404000-00013. PMID 11224270. 
  6. "Antidepressant-like effect of selective dopamine D1 receptor agonists in the behavioural despair animal model of depression". European Journal of Pharmacology 262 (1–2): 107–11. September 1994. doi:10.1016/0014-2999(94)90033-7. PMID 7813561. 
  7. "Sedative effects of the dopamine D1 receptor agonist A 68930 on rat open-field behavior". NeuroReport 11 (6): 1269–72. April 2000. doi:10.1097/00001756-200004270-00025. PMID 10817605. 
  8. "A 68930 and dihydrexidine inhibit locomotor activity and d-amphetamine-induced hyperactivity in rats: a role of inhibitory dopamine D(1/5) receptors in the prefrontal cortex?". Neuroscience 124 (1): 33–42. 2004. doi:10.1016/j.neuroscience.2003.11.016. PMID 14960337. 
  9. "Differences between A 68930 and SKF 82958 could suggest synergistic roles of D1 and D5 receptors". Pharmacology Biochemistry and Behavior 82 (3): 495–505. November 2005. doi:10.1016/j.pbb.2005.09.017. PMID 16318870.