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A-68930
IUPAC name

(1R,3S)-1-(Aminomethyl)-3-phenyl-3,4-dihydro-1H-isochromene-5,6-diol[1]
Identifiers
CAS number 130465-45-1 N, 130465-39-3 (HCl) YesY
PubChem 122324
ChemSpider 109076 YesY
MeSH A+68930
ChEMBL CHEMBL315468 N
Jmol-3D images Image 1
Properties
Molecular formula C16H17NO3
Molar mass 271.31 g mol−1
Exact mass 271.120843415 g mol-1
log P 1.175
Acidity (pKa) 9.491
Basicity (pKb) 4.506
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

A-68930 is a synthetic compound that acts as a selective dopamine receptor D1 partial agonist.[2][3] It is orally active and has antidepressant and anorectic effects in animals, producing wakefulness and tachycardia,[4][5][6][7] but without stimulant effects, instead producing sedation.[8][9] 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.[10]

References

  1. ^ PubChem 122324
  2. ^ DeNinno MP, Schoenleber R, Asin KE, MacKenzie R, Kebabian JW (November 1990). "(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. doi:10.1021/jm00173a005. PMID 1977907. 
  3. ^ DeNinno MP, Schoenleber R, MacKenzie R, Britton DR, Asin KE, Briggs C, Trugman JM, Ackerman M, Artman L, Bednarz L (June 1991). "A68930: a potent agonist selective for the dopamine D1 receptor". European Journal of Pharmacology 199 (2): 209–19. doi:10.1016/0014-2999(91)90459-4. PMID 1683288. 
  4. ^ Trampus M, Ferri N, Adami M, Ongini E (April 1993). "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. doi:10.1016/0014-2999(93)90823-Z. PMID 8100197. 
  5. ^ Christie MI, Smith GW (February 1994). "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. PMID 7906731. 
  6. ^ AI-Naser HA, Cooper SJ (April 1994). "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. PMID 11224270. 
  7. ^ D'Aquila PS, Collu M, Pani L, Gessa GL, Serra G (September 1994). "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. doi:10.1016/0014-2999(94)90033-7. PMID 7813561. 
  8. ^ Salmi P, Ahlenius S (April 2000). "Sedative effects of the dopamine D1 receptor agonist A 68930 on rat open-field behavior". Neuroreport 11 (6): 1269–72. doi:10.1097/00001756-200004270-00025. PMID 10817605. 
  9. ^ Isacson R, Kull B, Wahlestedt C, Salmi P (2004). "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. doi:10.1016/j.neuroscience.2003.11.016. PMID 14960337. 
  10. ^ Nergårdh R, Oerther S, Fredholm BB (November 2005). "Differences between A 68930 and SKF 82958 could suggest synergistic roles of D1 and D5 receptors". Pharmacology, Biochemistry, and Behavior 82 (3): 495–505. doi:10.1016/j.pbb.2005.09.017. PMID 16318870. 



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