Spiroxatrine | CAS#1054-88-2 | anxiolytic

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

MedKoo CAT#: 584390

CAS#: 1054-88-2

Description: 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

CAS# 1054-88-2

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 584390
Name: Spiroxatrine
CAS#: 1054-88-2
Chemical Formula: C22H25N3O3
Exact Mass: 379.19
Molecular Weight: 379.460
Elemental Analysis: C, 69.64; H, 6.64; N, 11.07; O, 12.65

Price and Availability

Size	Price	Availability
10mg	USD 325	2 Weeks
50mg	USD 1045	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	1.9	5.06

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.

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.

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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.

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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.

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Spiroxatrine featured