Eltoprazine HCl | DU-28853 | CAS#98206-09-8 | 5-HT antagonist

MedKoo Cat#: 528830 | Name: Eltoprazine HCl

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Description:

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

Eltoprazine, also known as DU-28853, is a 5-HT antagonist potentially for the treatment of attention deficit hyperactivity disorder (ADHD).

Chemical Structure

Eltoprazine HCl

CAS#98206-09-8 (HCl)

Theoretical Analysis

MedKoo Cat#: 528830

Name: Eltoprazine HCl

CAS#: 98206-09-8 (HCl)

Chemical Formula: C12H17ClN2O2

Exact Mass: 0.0000

Molecular Weight: 256.73

Elemental Analysis: C, 56.14; H, 6.67; Cl, 13.81; N, 10.91; O, 12.46

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 350.00	2 weeks
25mg	USD 650.00	2 weeks

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Related CAS #

98224-03-4 (free base) 98206-09-8 (HCl)

Synonym

DU-28853; DU28853; DU 28853 HCl; Eltoprazine HCl; Eltoprazine hydrochloride; MP 15; MP15; MP-15 HCl

IUPAC/Chemical Name

1-(2,3-dihydrobenzo[b][1,4]dioxin-5-yl)piperazine hydrochloride

InChi Key

JFSOSUNPIXJCIX-UHFFFAOYSA-N

InChi Code

InChI=1S/C12H16N2O2.ClH/c1-2-10(14-6-4-13-5-7-14)12-11(3-1)15-8-9-16-12;/h1-3,13H,4-9H2;1H

SMILES Code

[H]Cl.N1(C2=C3OCCOC3=CC=C2)CCNCC1

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:

Eltoprazine hydrochloride (DU 28853 hydrochloride) is an agonist at the 5-HT1A and 5-HT1B receptors and as an antagonist at the 5-HT2C receptor.

In vitro activity:

TBD

In vivo activity:

The microdialysis studies clearly showed that eltoprazine increased DA and NE release in both the mPFC and OFC, but only increased DA concentration in the NAc. In contrast, eltoprazine decreased 5-HT release in the mPFC and NAc (undetectable in the OFC). Remarkably, eltoprazine decreased impulsive choice, but increased impulsive action. Furthermore, brain stimulation was less rewarding following eltoprazine treatment in rats. Reference: Eur J Pharmacol. 2017 Jan 5;794:257-269. https://pubmed.ncbi.nlm.nih.gov/27866999/

	Solvent	mg/mL	mM
Solubility
	DMSO	25.5	99.33
	DMF	30.0	116.85
	Ethanol	25.0	97.38
	PBS (pH 7.2)	1.0	3.90
	Water	100.0	389.51

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 256.73 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. Wang Q, Chen J, Li M, Lv S, Xie Z, Li N, Wang N, Wang J, Luo F, Zhang W. Eltoprazine prevents levodopa-induced dyskinesias by reducing causal interactions for theta oscillations in the dorsolateral striatum and substantia nigra pars reticulate. Neuropharmacology. 2019 Apr;148:1-10. doi: 10.1016/j.neuropharm.2018.12.027. Epub 2019 Jan 3. PMID: 30612008. 2. Korte SM, Prins J, Van den Bergh FS, Oosting RS, Dupree R, Korte-Bouws GA, Westphal KG, Olivier B, Denys DA, Garland A, Güntürkün O. The 5-HT1A/1B-receptor agonist eltoprazine increases both catecholamine release in the prefrontal cortex and dopamine release in the nucleus accumbens and decreases motivation for reward and "waiting" impulsivity, but increases "stopping" impulsivity. Eur J Pharmacol. 2017 Jan 5;794:257-269. doi: 10.1016/j.ejphar.2016.11.024. Epub 2016 Nov 17. PMID: 27866999.

In vitro protocol:

TBD

In vivo protocol:

1: Svenningsson P, Rosenblad C, Af Edholm Arvidsson K, Wictorin K, Keywood C, Shankar B, Lowe DA, Björklund A, Widner H. Eltoprazine counteracts l-DOPA-induced dyskinesias in Parkinson's disease: a dose-finding study. Brain. 2015 Apr;138(Pt 4):963-73. doi: 10.1093/brain/awu409. Epub 2015 Feb 10. PubMed PMID: 25669730; PubMed Central PMCID: PMC5014080. 2: Korte SM, Prins J, Van den Bergh FS, Oosting RS, Dupree R, Korte-Bouws GA, Westphal KG, Olivier B, Denys DA, Garland A, Güntürkün O. The 5-HT(1A/1B)-receptor agonist eltoprazine increases both catecholamine release in the prefrontal cortex and dopamine release in the nucleus accumbens and decreases motivation for reward and "waiting" impulsivity, but increases "stopping" impulsivity. Eur J Pharmacol. 2017 Jan 5;794:257-269. doi: 10.1016/j.ejphar.2016.11.024. Epub 2016 Nov 17. PubMed PMID: 27866999. 3: Paolone G, Brugnoli A, Arcuri L, Mercatelli D, Morari M. Eltoprazine prevents levodopa-induced dyskinesias by reducing striatal glutamate and direct pathway activity. Mov Disord. 2015 Nov;30(13):1728-38. doi: 10.1002/mds.26326. Epub 2015 Jul 24. PubMed PMID: 26207892. 4: Bezard E, Tronci E, Pioli EY, Li Q, Porras G, Björklund A, Carta M. Study of the antidyskinetic effect of eltoprazine in animal models of levodopa-induced dyskinesia. Mov Disord. 2013 Jul;28(8):1088-96. doi: 10.1002/mds.25366. Epub 2013 Feb 6. PubMed PMID: 23389842. 5: Wigal SB, Duong S. Pharmacokinetic evaluation of eltoprazine. Expert Opin Drug Metab Toxicol. 2011 Jun;7(6):775-81. doi: 10.1517/17425255.2011.580275. Epub 2011 May 6. Review. PubMed PMID: 21548716. 6: Ghiglieri V, Mineo D, Vannelli A, Cacace F, Mancini M, Pendolino V, Napolitano F, di Maio A, Mellone M, Stanic J, Tronci E, Fidalgo C, Stancampiano R, Carta M, Calabresi P, Gardoni F, Usiello A, Picconi B. Modulation of serotonergic transmission by eltoprazine in L-DOPA-induced dyskinesia: Behavioral, molecular, and synaptic mechanisms. Neurobiol Dis. 2016 Feb;86:140-53. doi: 10.1016/j.nbd.2015.11.022. Epub 2015 Nov 27. PubMed PMID: 26639853. 7: Carta M, Cenci MA. On the Effect of Eltoprazine in Dyskinetic Hemiparkinsonian Rats. Mov Disord. 2016 Jan;31(1):149. doi: 10.1002/mds.26519. Epub 2016 Jan 8. PubMed PMID: 26749366. 8: Olivier B, Herremans A, Mos J, van Drimmelen M, Tulp M, van Oorschot R, Hijzen T. Discriminative stimulus properties of eltoprazine in the pigeon. Pharmacol Biochem Behav. 1999 Oct;64(2):421-7. PubMed PMID: 10515324. 9: Gommans J, Hijzen TH, Maes RA, Olivier B. Two-lever drug-drug discrimination with the 5-HT1 receptor agonists flesinoxan and eltoprazine. Int J Neuropsychopharmacol. 2000 Sep;3(3):221-228. PubMed PMID: 11343599. 10: Pinna A, Ko WK, Costa G, Tronci E, Fidalgo C, Simola N, Li Q, Tabrizi MA, Bezard E, Carta M, Morelli M. Antidyskinetic effect of A2A and 5HT1A/1B receptor ligands in two animal models of Parkinson's disease. Mov Disord. 2016 Apr;31(4):501-11. doi: 10.1002/mds.26475. Epub 2016 Feb 12. PubMed PMID: 26871939. 11: Tronci E, Fidalgo C, Stancampiano R, Carta M. Effect of selective and non-selective serotonin receptor activation on L-DOPA-induced therapeutic efficacy and dyskinesia in parkinsonian rats. Behav Brain Res. 2015 Oct 1;292:300-4. doi: 10.1016/j.bbr.2015.06.034. Epub 2015 Jun 25. PubMed PMID: 26119238. 12: de Boer SF, Lesourd M, Mocaer E, Koolhaas JM. Selective antiaggressive effects of alnespirone in resident-intruder test are mediated via 5-hydroxytryptamine1A receptors: A comparative pharmacological study with 8-hydroxy-2-dipropylaminotetralin, ipsapirone, buspirone, eltoprazine, and WAY-100635. J Pharmacol Exp Ther. 1999 Mar;288(3):1125-33. PubMed PMID: 10027850. 13: Gommans J, Hijzen TH, Maes RA, Olivier B. Discriminative stimulus properties of eltoprazine. Life Sci. 1997;61(1):11-9. PubMed PMID: 9200664. 14: Mos J, van Aken HH, van Oorschot R, Olivier B. Chronic treatment with eltoprazine does not lead to tolerance in its anti-aggressive action, in contrast to haloperidol. Eur Neuropsychopharmacol. 1996 Mar;6(1):1-7. PubMed PMID: 8866931. 15: de Koning P, Mak M, de Vries MH, Allsopp LF, Stevens RB, Verbruggen R, Van den Borre R, van Peteghem P, Kohen D, Arumainayagam M, et al. Eltoprazine in aggressive mentally handicapped patients: a double-blind, placebo- and baseline-controlled multi-centre study. The Eltoprazine Aggression Research Group. Int Clin Psychopharmacol. 1994 Sep;9(3):187-94. PubMed PMID: 7814828. 16: Rocha B, Rigo M, Di Scala G, Sandner G, Hoyer D. Chronic mianserin or eltoprazine treatment in rats: effects on the elevated plus-maze test and on limbic 5-HT2C receptor levels. Eur J Pharmacol. 1994 Sep 1;262(1-2):125-31. PubMed PMID: 7813563. 17: Olivier B, Mos J, Rasmussen D. Behavioural pharmacology of the serenic, eltoprazine. Drug Metabol Drug Interact. 1990;8(1-2):31-83. Review. PubMed PMID: 2091890. 18: Schipper J, Tulp MT, Sijbesma H. Neurochemical profile of eltoprazine. Drug Metabol Drug Interact. 1990;8(1-2):85-114. PubMed PMID: 1982626. 19: Mos J, Olivier B, Poth M, Van Oorschot R, Van Aken H. The effects of dorsal raphe administration of eltoprazine, TFMPP and 8-OH-DPAT on resident intruder aggression in the rat. Eur J Pharmacol. 1993 Jul 20;238(2-3):411-5. PubMed PMID: 8405111. 20: Ybema CE, Slangen JL, Olivier B, Mos J. Discriminative stimulus properties of the serotonergic compound eltoprazine. J Pharmacol Exp Ther. 1992 Mar;260(3):1045-51. PubMed PMID: 1532031.