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MedKoo Cat#: 584390 | Name: Spiroxatrine
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Description:

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

Spiroxatrine is a potent dopamine antagonist that most likely functions as an agonist at the 5-HT1A receptor. This compound is similar to buspirone in that it has a prominent dopamine antagonist component and has been found to produce greater anxiolytic effects when combined with buspirone.

Chemical Structure

Spiroxatrine
Spiroxatrine
CAS#1054-88-2

Theoretical Analysis

MedKoo Cat#: 584390

Name: Spiroxatrine

CAS#: 1054-88-2

Chemical Formula: C22H25N3O3

Exact Mass: 379.1896

Molecular Weight: 379.46

Elemental Analysis: C, 69.64; H, 6.64; N, 11.07; O, 12.65

Price and Availability

Size Price Availability Quantity
10mg USD 325.00 2 Weeks
50mg USD 1,045.00 2 Weeks
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Related CAS #
No Data
Synonym
Spiroxatrine; Espiroxatrina; R 5188
IUPAC/Chemical Name
8-[(2,3-Dihydro-1,4-benzodioxin-2-yl)methyl]-1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one
InChi Key
JVGBTTIJPBFLTE-UHFFFAOYSA-N
InChi Code
InChI=1S/C22H25N3O3/c26-21-22(25(16-23-21)17-6-2-1-3-7-17)10-12-24(13-11-22)14-18-15-27-19-8-4-5-9-20(19)28-18/h1-9,18H,10-16H2,(H,23,26)
SMILES Code
O=C1NCN(C2=CC=CC=C2)C13CCN(CC4OC5=CC=CC=C5OC4)CC3
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Spiroxatrine is a dual antagonist of 5-HT1α and α2-adrenergic, with Ki values of 3.94, 224000, 118.5 nM for 5-HT1α, 5-HT1β and 5-HT2, respectively.
In vitro activity:
To be determined
In vivo activity:
Results from this study show that the 5-HT(1A) receptor, but not the 5-HT(2) or 5-HT(3) receptor, plays a significant role in pain relief in a murine model. Intrathecal administration of spiroxatrine, but not RS 102221 nor MDL 72222, significantly attenuated the increased hindpaw withdrawal latencies induced by intra-periaqueductal gray administration of morphine in rats with nerve injury and in rats with inflammation. Reference: Neuroscience. 2002;112(2):399-407. https://pubmed.ncbi.nlm.nih.gov/12044457/
Solvent mg/mL mM comments
Solubility
DMSO 1.9 5.06
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 379.46 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
Formulation protocol:
1. Liu ZY, Zhuang DB, Lunderberg T, Yu LC. Involvement of 5-hydroxytryptamine(1A) receptors in the descending anti-nociceptive pathway from periaqueductal gray to the spinal dorsal horn in intact rats, rats with nerve injury and rats with inflammation. Neuroscience. 2002;112(2):399-407. doi: 10.1016/s0306-4522(02)00038-6. PMID: 12044457. 2. Terrón JA, Ransanz V, Ibarra M, Hong E, Villalón CM. Alpha 1-adrenoceptor blocking properties of spiroxatrine in rat aorta. Life Sci. 1992;51(1):PL1-6. doi: 10.1016/0024-3205(92)90222-b. PMID: 1352025.
In vitro protocol:
To be determined
In vivo protocol:
1. Liu ZY, Zhuang DB, Lunderberg T, Yu LC. Involvement of 5-hydroxytryptamine(1A) receptors in the descending anti-nociceptive pathway from periaqueductal gray to the spinal dorsal horn in intact rats, rats with nerve injury and rats with inflammation. Neuroscience. 2002;112(2):399-407. doi: 10.1016/s0306-4522(02)00038-6. PMID: 12044457. 2. Terrón JA, Ransanz V, Ibarra M, Hong E, Villalón CM. Alpha 1-adrenoceptor blocking properties of spiroxatrine in rat aorta. Life Sci. 1992;51(1):PL1-6. doi: 10.1016/0024-3205(92)90222-b. PMID: 1352025.
1: McBride WJ, Murphy JM, Lumeng L, Li TK. Spiroxatrine augments fluoxetine-induced reduction of ethanol intake by the P line of rats. Pharmacol Biochem Behav. 1989 Oct;34(2):381-6. PubMed PMID: 2533688. 2: Laurila JM, Wissel G, Xhaard H, Ruuskanen JO, Johnson MS, Scheinin M. Involvement of the first transmembrane segment of human α(2) -adrenoceptors in the subtype-selective binding of chlorpromazine, spiperone and spiroxatrine. Br J Pharmacol. 2011 Nov;164(5):1558-72. doi: 10.1111/j.1476-5381.2011.01520.x. PubMed PMID: 21649638; PubMed Central PMCID: PMC3221108. 3: Herrick-Davis K, Titeler M. [3H]spiroxatrine: a 5-HT1A radioligand with agonist binding properties. J Neurochem. 1988 Feb;50(2):528-33. PubMed PMID: 2961850. 4: Barrett JE, Hoffmann SM, Olmstead SN, Foust MJ, Harrod C, Weissman BA. Behavioral and neurochemical effects of the serotonin (5-HT)1A receptor ligand spiroxatrine. Psychopharmacology (Berl). 1989;97(3):319-25. PubMed PMID: 2524083. 5: Terrón JA, Ibarra M, Ransanz V, Hong E, Villalón CM. [The alpha-antiadrenergic properties of spiroxatrine, a ligand of serotonergic 5-HT1A receptors]. Arch Inst Cardiol Mex. 1993 Jul-Aug;63(4):289-95. Spanish. PubMed PMID: 8105762. 6: Nelson DL, Monroe PJ, Lambert G, Yamamura HI. [3H]spiroxatrine labels a serotonin1A-like site in the rat hippocampus. Life Sci. 1987 Sep 28;41(13):1567-76. PubMed PMID: 2957559. 7: Nikam SS, Martin AR, Nelson DL. Serotonergic properties of spiroxatrine enantiomers. J Med Chem. 1988 Oct;31(10):1965-8. PubMed PMID: 2902227. 8: Honda M, Ono H. Differential effects of (R)- and (S)-8-hydroxy-2-(di-n-propylamino)tetralin on the monosynaptic spinal reflex in rats. Eur J Pharmacol. 1999 Jun 4;373(2-3):171-9. PubMed PMID: 10414436. 9: Hajagos-Toth J, Bota J, Ducza E, Csanyi A, Tiszai Z, Borsodi A, Samavati R, Benyhe S, Gaspar R. The effects of estrogen on the α2-adrenergic receptor subtypes in rat uterine function in late pregnancy in vitro. Croat Med J. 2016 Apr 23;57(2):100-9. PubMed PMID: 27106352; PubMed Central PMCID: PMC4856191. 10: Costall B, Naylor RJ. Dopamine antagonistic effects of a series of analogues of oxiperomide and spiroxatrine measured behaviourally in the rodent. J Pharm Pharmacol. 1978 Nov;30(11):693-8. PubMed PMID: 31432. 11: Manahan-Vaughan D, Anwyl R, Rowan MJ. The azapirone metabolite 1-(2-pyrimidinyl)piperazine depresses excitatory synaptic transmission in the hippocampus of the alert rat via 5-HT1A receptors. Eur J Pharmacol. 1995 Dec 29;294(2-3):617-24. PubMed PMID: 8750726. 12: Nelson DL, Taylor EW. Spiroxatrine: a selective serotonin1A receptor antagonist. Eur J Pharmacol. 1986 May 13;124(1-2):207-8. PubMed PMID: 3720840. 13: Terrón JA, Ransanz V, Ibarra M, Hong E, Villalón CM. Alpha 1-adrenoceptor blocking properties of spiroxatrine in rat aorta. Life Sci. 1992;51(1):PL1-6. PubMed PMID: 1352025. 14: Guimarães S, Figueiredo IV, Caramona MM, Moura D, Paiva MQ. Prejunctional alpha2A-autoreceptors in the human gastric and ileocolic arteries. Naunyn Schmiedebergs Arch Pharmacol. 1998 Aug;358(2):207-11. PubMed PMID: 9750006. 15: Gál A, Ducza E, Minorics R, Klukovits A, Gálik M, Falkay G, Gáspár R. The roles of alpha2-adrenoceptor subtypes in the control of cervical resistance in the late-pregnant rat. Eur J Pharmacol. 2009 Aug 1;615(1-3):193-200. doi: 10.1016/j.ejphar.2009.04.067. Epub 2009 May 15. PubMed PMID: 19450576. 16: Kolassa N, Beller KD, Sanders KH. Involvement of brain 5-HT1A receptors in the hypotensive response to urapidil. Am J Cardiol. 1989 Aug 15;64(7):7D-10D. Review. PubMed PMID: 2569265. 17: Corrado S, Battisti UM, Sorbi C, Tait A, Malfacini D, Camarda V, Calò G, Brasili L. Synthesis and Structure-Activity Relationships of Triazaspirodecanone Derivatives as Nociceptin/Orphanin FQ Receptor Ligands. Chem Biol Drug Des. 2015 Oct;86(4):447-58. doi: 10.1111/cbdd.12505. Epub 2015 Jan 20. PubMed PMID: 25546401. 18: Manahan-Vaughan D, Anwyl R, Rowan MJ. 5-HT1A receptor-mediated inhibition in the hippocampus of the alert rat--effects of repeated gepirone treatment. Eur J Pharmacol. 1994 Aug 1;260(2-3):149-55. PubMed PMID: 7988638. 19: Valenta B, Singer EA. Hypotensive effects of 8-hydroxy-2-(di-n-propylamino)tetralin and 5-methylurapidil following stereotaxic microinjection into the ventral medulla of the rat. Br J Pharmacol. 1990 Apr;99(4):713-6. PubMed PMID: 1972893; PubMed Central PMCID: PMC1917564. 20: Carli M, Lazarova M, Tatarczynska E, Samanin R. Stimulation of 5-HT1A receptors in the dorsal hippocampus impairs acquisition and performance of a spatial task in a water maze. Brain Res. 1992 Nov 6;595(1):50-6. PubMed PMID: 1467958.