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MedKoo Cat#: 145771 | Name: A-86929

Description:

WARNING: This product is for research use only, not for human or veterinary use.

A-86929 is a synthetic compound that acts as a selective dopamine D₁ receptor agonist. It was developed as a potential treatment for Parkinson's disease.

Chemical Structure

A-86929
A-86929
CAS#171961-95-8

Theoretical Analysis

MedKoo Cat#: 145771

Name: A-86929

CAS#: 171961-95-8

Chemical Formula: C18H21NO2S

Exact Mass: 315.1300

Molecular Weight: 315.43

Elemental Analysis: C, 68.54; H, 6.71; N, 4.44; O, 10.14; S, 10.16

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
A-86929; A86929; A 86929;
IUPAC/Chemical Name
(5aR,11bS)-2-propyl-4,5,5a,6,7,11b-hexahydrobenzo[f]thieno[2,3-c]quinoline-9,10-diol
InChi Key
REHAKLRYABHSQJ-KDOFPFPSSA-N
InChi Code
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
SMILES Code
[H][C@@]12CCC3=CC(O)=C(O)C=C3[C@@]1([H])C4=C(CN2)SC(CCC)=C4
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 315.43 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Martin YC. The Discovery of Novel Selective D1 Dopaminergic Agonists: A-68930, A-77636, A-86929, and ABT-413. Int J Med Chem. 2011;2011:424535. doi: 10.1155/2011/424535. Epub 2011 Mar 24. PMID: 25954518; PMCID: PMC4412209. 2: Giardina WJ, Williams M. Adrogolide HCl (ABT-431; DAS-431), a prodrug of the dopamine D1 receptor agonist, A-86929: preclinical pharmacology and clinical data. CNS Drug Rev. 2001 Fall;7(3):305-16. doi: 10.1111/j.1527-3458.2001.tb00201.x. PMID: 11607045; PMCID: PMC6741696. 3: Li H, Mirabel R, Zimmerman J, Ghiviriga I, Phidd DK, Horenstein N, Urs NM. Structure-Functional Selectivity Relationship Studies on A-86929 Analogs and Small Aryl Fragments toward the Discovery of Biased Dopamine D1 Receptor Agonists. ACS Chem Neurosci. 2022 Jun 15;13(12):1818-1831. doi: 10.1021/acschemneuro.2c00235. Epub 2022 Jun 6. PMID: 35658399. 4: Hajra S, Bar S. Catalytic enantioselective synthesis of A-86929, a dopamine D1 agonist. Chem Commun (Camb). 2011 Apr 7;47(13):3981-2. doi: 10.1039/c1cc10263j. Epub 2011 Feb 14. PMID: 21321777. 5: Pearce RK, Jackson M, Britton DR, Shiosaki K, Jenner P, Marsden CD. Actions of the D1 agonists A-77636 and A-86929 on locomotion and dyskinesia in MPTP- treated L-dopa-primed common marmosets. Psychopharmacology (Berl). 1999 Feb;142(1):51-60. doi: 10.1007/s002130050861. PMID: 10102782. 6: 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. 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. J Pharmacol Exp Ther. 1996 Jan;276(1):150-60. PMID: 8558425. 7: Michaelides MR, Hong Y, DiDomenico S Jr, Asin KE, Britton DR, Lin CW, Williams M, Shiosaki K. (5aR,11bS)-4,5,5a,6,7,11b-hexahydro-2-propyl-3-thia-5-azacyclopent-1- ena[c]-phenanthrene-9,10-diol (A-86929): a potent and selective dopamine D1 agonist that maintains behavioral efficacy following repeated administration and characterization of its diacetyl prodrug (ABT-431). J Med Chem. 1995 Sep 1;38(18):3445-7. doi: 10.1021/jm00018a002. PMID: 7658429. 8: Ehrlich PP, Ralston JW, Michaelides MR. 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). J Org Chem. 1997 May 2;62(9):2782-2785. doi: 10.1021/jo970066l. PMID: 11671640. 9: Asin KE, Domino EF, Nikkel A, Shiosaki K. The selective dopamine D1 receptor agonist A-86929 maintains efficacy with repeated treatment in rodent and primate models of Parkinson's disease. J Pharmacol Exp Ther. 1997 Apr;281(1):454-9. PMID: 9103530. 10: Shiosaki K, Asin KE, Britton DR, Giardina WJ, Bednarz L, Mahan L, Mikusa J, Nikkel A, Wismer C. Hyperactivity and behavioral seizures in rodents following treatment with the dopamine D1 receptor agonists A-86929 and ABT-431. Eur J Pharmacol. 1996 Dec 19;317(2-3):183-90. doi: 10.1016/s0014-2999(96)00718-2. PMID: 8997599. 11: Yamashita M, Yamada K, Tomioka K. Construction of arene-fused-piperidine motifs by asymmetric addition of 2-trityloxymethylaryllithiums to nitroalkenes: the asymmetric synthesis of a dopamine D1 full agonist, A-86929. J Am Chem Soc. 2004 Feb 25;126(7):1954-5. doi: 10.1021/ja031760n. PMID: 14971926. 12: Grondin R, Bédard PJ, Britton DR, Shiosaki K. Potential therapeutic use of the selective dopamine D1 receptor agonist, A-86929: an acute study in parkinsonian levodopa-primed monkeys. Neurology. 1997 Aug;49(2):421-6. doi: 10.1212/wnl.49.2.421. PMID: 9270571. 13: Gu YG, Bayburt EK, Michaelides MR, Lin CW, Shiosaki K. trans-2,6-,3,6- and 4,6-diaza-5,6,6a,7,8,12b-hexahydro-benzo[c]phenanthrene-10,11- diols as dopamine agonists. Bioorg Med Chem Lett. 1999 May 17;9(10):1341-6. doi: 10.1016/s0960-894x(99)00214-0. PMID: 10360732. 14: Rascol O, Blin O, Thalamas C, Descombes S, Soubrouillard C, Azulay P, Fabre N, Viallet F, Lafnitzegger K, Wright S, Carter JH, Nutt JG. ABT-431, a D1 receptor agonist prodrug, has efficacy in Parkinson's disease. Ann Neurol. 1999 Jun;45(6):736-41. doi: 10.1002/1531-8249(199906)45:6<736::aid-ana7>3.0.co;2-f. PMID: 10360765. 15: Zhang J, Xiong B, Zhen X, Zhang A. Dopamine D1 receptor ligands: where are we now and where are we going. Med Res Rev. 2009 Mar;29(2):272-94. doi: 10.1002/med.20130. PMID: 18642350. 16: Okumu FW, Lee RY, Blanchard JD, Queirolo A, Woods CM, Lloyd PM, Okikawa J, Gonda I, Farr SJ, Rubsamen R, Adjei AL, Bertz RJ. Evaluation of the AERx pulmonary delivery system for systemic delivery of a poorly soluble selective D-1 agonist, ABT-431. Pharm Res. 2002 Jul;19(7):1009-12. doi: 10.1023/a:1016559707084. PMID: 12180532. 17: Treseder SA, Jackson M, Jenner P. The effects of central aromatic amino acid DOPA decarboxylase inhibition on the motor actions of L-DOPA and dopamine agonists in MPTP-treated primates. Br J Pharmacol. 2000 Apr;129(7):1355-64. doi: 10.1038/sj.bjp.0703189. PMID: 10742291; PMCID: PMC1571971. 18: Gleason SD, Witkin JM. Effects of dopamine D1 receptor full agonists in rats trained to discriminate SKF 38393. Behav Pharmacol. 2004 Feb;15(1):85-9. doi: 10.1097/00008877-200402000-00010. PMID: 15075630. 19: Zheng Y, Marsh KC, Bertz RJ, El-Shourbagy T, Adjei AL. Pulmonary delivery of a dopamine D-1 agonist, ABT-431, in dogs and humans. Int J Pharm. 1999 Nov 30;191(2):131-40. doi: 10.1016/s0378-5173(99)00296-3. PMID: 10564839. 20: Michaelides MR, Hong Y, DiDomenico S Jr, Bayburt EK, Asin KE, Britton DR, Lin CW, Shiosaki K. Substituted hexahydrobenzo[f]thieno[c]quinolines as dopamine D1-selective agonists: synthesis and biological evaluation in vitro and in vivo. J Med Chem. 1997 May 23;40(11):1585-99. doi: 10.1021/jm970038v. PMID: 9171869.

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