A-86929

Last updated

A-86929
A-86929.svg
Names
Preferred IUPAC name
(5aR,11bS)-2-Propyl-4,5,5a,6,7,11b-hexahydrobenzo[f]thieno[2,3-c]quinoline-9,10-diol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C18H21NO2S/c1-2-3-11-7-13-17(22-11)9-19-14-5-4-10-6-15(20)16(21)8-12(10)18(13)14/h6-8,14,18-21H,2-5,9H2,1H3/t14-,18+/m1/s1 Yes check.svgY
    Key: REHAKLRYABHSQJ-KDOFPFPSSA-N Yes check.svgY
  • InChI=1/C18H21NO2S/c1-2-3-11-7-13-17(22-11)9-19-14-5-4-10-6-15(20)16(21)8-12(10)18(13)14/h6-8,14,18-21H,2-5,9H2,1H3/t14-,18+/m1/s1
    Key: REHAKLRYABHSQJ-KDOFPFPSBO
  • Oc1cc3c(cc1O)CCC4C3c2cc(CCC)sc2CN4
Properties
C18H21NO2S
Molar mass 315.429 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

A-86929 is a synthetic compound that acts as a selective dopamine receptor D1 agonist. [1] [2] It was developed as a possible treatment for Parkinson's disease, [3] as well as for other applications such as treatment of cocaine addiction, [4] [5] but while it had reasonable efficacy in humans it also caused dyskinesias and has not been continued. [6] [7] It has mainly been used as its diacetate ester prodrug adrogolide (ABT-431), which has better bioavailability. [8] [9]

Adrogolide Adrogolide.svg
Adrogolide

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References

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  2. Ehrlich PP, Ralston JW, Michaelides MR (May 1997). "An Efficient Enantioselective Synthesis of the D1 Agonist (5aR,11bS)-4,5,5a,6,7,11b-Hexahydro-2-propyl-3-thia- 5-azacyclopenta[c]phenanthrene-9,10-diol (A-86929)". The Journal of Organic Chemistry. 62 (9): 2782–2785. doi:10.1021/jo970066l. PMID   11671640.
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  8. Shiosaki K, Jenner P, Asin KE, Britton DR, Lin CW, Michaelides M, Smith L, Bianchi B, Didomenico S, Hodges L, Hong Y, Mahan L, Mikusa J, Miller T, Nikkel A, Stashko M, Witte D, Williams M (January 1996). "ABT-431: the diacetyl prodrug of A-86929, a potent and selective dopamine D1 receptor agonist: in vitro characterization and effects in animal models of Parkinson's disease". The Journal of Pharmacology and Experimental Therapeutics. 276 (1): 150–60. PMID   8558425.
  9. Giardina WJ, Williams M (2001). "Adrogolide HCl (ABT-431; DAS-431), a prodrug of the dopamine D1 receptor agonist, A-86929: preclinical pharmacology and clinical data". CNS Drug Reviews. 7 (3): 305–16. doi:10.1111/j.1527-3458.2001.tb00201.x. PMC   6741696 . PMID   11607045.