A-68930

Last updated
A-68930
Stereo, Kekule skeletal formula of A-68930 A-68930 Structure.svg
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
PubChem CID
UNII
  • InChI=1S/C16H17NO3/c17-9-15-11-6-7-13(18)16(19)12(11)8-14(20-15)10-4-2-1-3-5-10/h1-7,14-15,18-19H,8-9,17H2/t14-,15-/m0/s1 X mark.svgN
    Key: SUHGRZPINGKYNV-GJZGRUSLSA-N Yes check.svgY
  • Oc1c(O)ccc2c1C[C@H](O[C@H]2CN)c3ccccc3
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).
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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. ↑ 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.
  2. ↑ 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.
  3. ↑ 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.
  4. ↑ 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.
  5. ↑ 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. doi:10.1097/00008877-199404000-00013. PMID   11224270.
  6. ↑ 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.
  7. ↑ 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. S2CID   35263421.
  8. ↑ 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. S2CID   19913930.
  9. ↑ 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. S2CID   23281483.


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