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MedKoo Cat#: 326883 | Name: Fluparoxan HCl

Description:

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

Fluparoxan, also known as GR-50360; GR-50360A, is a potent α2-adrenergic receptor antagonist (pKB = 7.9) with excellent α2/α1 selectivity (2630 fold). It was shown to possess central α2-adrenoceptor antagonist activity after oral doses in man and was patented as an antidepressant by Glaxo in the early 1980s, but its development was discontinued when the compound failed to show a clear clinical advantage over existing therapies.

Chemical Structure

Fluparoxan HCl
Fluparoxan HCl
CAS#105226-30-0 (HCl)

Theoretical Analysis

MedKoo Cat#: 326883

Name: Fluparoxan HCl

CAS#: 105226-30-0 (HCl)

Chemical Formula: C10H11ClFNO2

Exact Mass:

Molecular Weight: 231.65

Elemental Analysis: C, 51.85; H, 4.79; Cl, 15.30; F, 8.20; N, 6.05; O, 13.81

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
GR-50360; GR50360; GR 50360; GR-50360A; Fluparoxan hydrochloride
IUPAC/Chemical Name
(3aS,9aS)-5-fluoro-2,3,3a,9a-tetrahydro-1H-benzo[5,6][1,4]dioxino[2,3-c]pyrrole hydrochloride
InChi Key
JNYKORXHNIRXSA-OZZZDHQUSA-N
InChi Code
InChI=1S/C10H10FNO2.ClH/c11-6-2-1-3-7-10(6)14-9-5-12-4-8(9)13-7;/h1-3,8-9,12H,4-5H2;1H/t8-,9-;/m0./s1
SMILES Code
FC1=C2O[C@]3([H])[C@](OC2=CC=C1)([H])CNC3.[H]Cl
Appearance
Solid powder
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
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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
Related CAS# 105182-47-6 ((3aR, 9aR)-Fluparoxan) 105226-30-0 ((3aR, 9aR)-Fluparoxan hydrochloride)

Preparing Stock Solutions

The following data is based on the product molecular weight 231.65 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
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Facilitation of constitutive alpha(2A)-adrenoceptor activity by both single amino acid mutation (Thr(373)Lys) and g(alphao) protein coexpression: evidence for inverse agonism. J Pharmacol Exp Ther. 2000 Feb;292(2):654-63. PubMed PMID: 10640303. 5: Millan MJ, Newman-Tancredi A, Audinot V, Cussac D, Lejeune F, Nicolas JP, Cogé F, Galizzi JP, Boutin JA, Rivet JM, Dekeyne A, Gobert A. Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states. Synapse. 2000 Feb;35(2):79-95. PubMed PMID: 10611634. 6: Newman-Tancredi A, Nicolas JP, Audinot V, Gavaudan S, Verrièle L, Touzard M, Chaput C, Richard N, Millan MJ. Actions of alpha2 adrenoceptor ligands at alpha2A and 5-HT1A receptors: the antagonist, atipamezole, and the agonist, dexmedetomidine, are highly selective for alpha2A adrenoceptors. Naunyn Schmiedebergs Arch Pharmacol. 1998 Aug;358(2):197-206. PubMed PMID: 9750005. 7: Beresford AP, Ellis WJ, Ayrton J, Johnson MA, Lewis DF. Cytochrome P4501A (CYP1A) induction in rat and man by the benzodioxino derivative, fluparoxan. Xenobiotica. 1997 Feb;27(2):159-73. PubMed PMID: 9058530. 8: Tellez S, Colpaert F, Marien M. Acetylcholine release in the rat prefrontal cortex in vivo: modulation by alpha 2-adrenoceptor agonists and antagonists. J Neurochem. 1997 Feb;68(2):778-85. PubMed PMID: 9003069. 9: Vayssettes-Courchay C, Bouysset F, Cordi AA, Laubie M, Verbeuren TJ. A comparative study of the reversal by different alpha 2-adrenoceptor antagonists of the central sympatho-inhibitory effect of clonidine. Br J Pharmacol. 1996 Feb;117(3):587-593. PubMed PMID: 8821553; PubMed Central PMCID: PMC1909310. 10: Jordan S, Jackson HC, Nutt DJ, Handley SL. Discriminative stimulus produced by the imidazoline I2 site ligand, 2 -BFI. J Psychopharmacol. 1996 Jan;10(4):273-8. doi: 10.1177/026988119601000403. PubMed PMID: 22302973. 11: Altria KD. Method validation. Methods Mol Biol. 1996;52:83-97. PubMed PMID: 8746681. 12: Kitchin J, Borthwick AD, Brodie AC, Cherry PC, Crame AJ, Pipe AJ, Procopiou PA, Seaman MA, Turnbull JP. Synthesis of benzodioxinopyrroles as selective alpha 2-adrenoceptor antagonists. Bioorg Med Chem. 1995 Dec;3(12):1595-603. PubMed PMID: 8770384. 13: Abou-Saleh MT, Anderson DN, Collins J, Hughes K, Cattell RJ, Hamon CG, Blair JA. The role of pterins in depression and the effects of antidepressive therapy. Biol Psychiatry. 1995 Oct 1;38(7):458-63. PubMed PMID: 8672606. 14: Johnson MA, Blackwell CP, Smith J. Antagonism of the effects of clonidine by the alpha 2-adrenoceptor antagonist, fluparoxan. Br J Clin Pharmacol. 1995 May;39(5):477-83. PubMed PMID: 7669482; PubMed Central PMCID: PMC1365053. 15: Le Bon O, Lion K, Verbanck P, Kornreich C. Fluparoxan in male erectile disorder: a case report. J Psychopharmacol. 1995 Jan;9(1):67-8. doi: 10.1177/026988119500900111. PubMed PMID: 22298696. 16: Jordan S, Jackson HC, Nutt DJ, Handley SL. Discriminative stimulus properties of ethoxy idazoxan. J Psychopharmacol. 1995 Jan;9(3):228-33. doi: 10.1177/026988119500900305. PubMed PMID: 22297762. 17: Millan MJ, Bervoets K, Rivet JM, Widdowson P, Renouard A, Le Marouille-Girardon S, Gobert A. Multiple alpha-2 adrenergic receptor subtypes. II. Evidence for a role of rat R alpha-2A adrenergic receptors in the control of nociception, motor behavior and hippocampal synthesis of noradrenaline. J Pharmacol Exp Ther. 1994 Sep;270(3):958-72. PubMed PMID: 7932208. 18: Renouard A, Widdowson PS, Millan MJ. Multiple alpha 2 adrenergic receptor subtypes. I. Comparison of [3H]RX821002-labeled rat R alpha-2A adrenergic receptors in cerebral cortex to human H alpha2A adrenergic receptor and other populations of alpha-2 adrenergic subtypes. J Pharmacol Exp Ther. 1994 Sep;270(3):946-57. PubMed PMID: 7932207. 19: Abou-Saleh MT, Collins J, George A, Rommelspacher H. Adrenoceptor activity and adenylate cyclase inhibition in depression. Br J Psychiatry. 1994 Aug;165(2):276-7. PubMed PMID: 7953054. 20: Jordan S, Jackson HC, Nutt DJ, Handley SL. Central alpha-2 adrenoceptors are responsible for a clonidine-induced cue in a rat drug discrimination paradigm. Psychopharmacology (Berl). 1993;110(1-2):209-12. PubMed PMID: 7870887.