Eticlopride HCl | FLB 131 | CAS# 84226-12-0 | 97612-24-3 | D2 dopamine receptor

MedKoo Cat#: 326812 | Name: Eticlopride HCl

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Description:

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

Eticlopride, also known as FLB 131, is a substituted benzamide analog with high affinity and selectivity for dopamine (DA) D2-like receptors that was initially developed as a potential antipsychotic agent. It is primarily used in pharmacological research. Eticlopride accelerates extinction and delays reacquisition of food self-administration in rats. Eticlopride induce microcatalepsy during operant performance in rats.

Chemical Structure

Eticlopride HCl

CAS#97612-24-3 (HCl)

Theoretical Analysis

MedKoo Cat#: 326812

Name: Eticlopride HCl

CAS#: 97612-24-3 (HCl)

Chemical Formula: C17H26Cl2N2O3

Exact Mass: 0.0000

Molecular Weight: 377.31

Elemental Analysis: C, 54.12; H, 6.95; Cl, 18.79; N, 7.42; O, 12.72

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 #

97612-24-3 (HCl) 84226-12-0 (free base)

Synonym

FLB 131; FLB131; FLB-131; Eticlopride hydrochloride; Eticlopride HCl; S-(−)-Eticlopride; (−)-Eticlopride

IUPAC/Chemical Name

(S)-3-chloro-5-ethyl-N-((1-ethylpyrrolidin-2-yl)methyl)-6-hydroxy-2-methoxybenzamide hydrochloride

InChi Key

HFJFXXDHVWLIKX-YDALLXLXSA-N

InChi Code

InChI=1S/C17H25ClN2O3.ClH/c1-4-11-9-13(18)16(23-3)14(15(11)21)17(22)19-10-12-7-6-8-20(12)5-2;/h9,12,21H,4-8,10H2,1-3H3,(H,19,22);1H/t12-;/m0./s1

SMILES Code

O=C(NC[C@H]1N(CC)CCC1)C2=C(O)C(CC)=CC(Cl)=C2OC.[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# CAS#97612-24-3 (Eticlopride free base). CAS# 84226-12-0 (Eticlopride HCl).

Product Data

Product Data

Instruction

View handling instruction

Biological target:

D2 and D3 antagonist (D3 > D2).

In vitro activity:

TBD

In vivo activity:

There were 21 rats assigned to the SAL condition and 22 rats assigned to the ETIC (eticlopride) condition. For active lever responding there were significant effects of TIME [F(6,234) = 39.3] and EXTDRUG [F(1,39) = 25.3], and a significant TIME X EXTDRUG interaction [F(6,234) = 7.6; all P’s < 0.001]. Eticlopride accelerated extinction responding across the seven days of the Extinction phase. Reference: Behav Pharmacol. 2013 Dec; 24(8): 633–639. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3896390/

	Solvent	mg/mL	mM
Solubility
	DMSO	25.0	66.26
	DMF	25.0	66.26
	Ethanol	30.0	79.51
	Water	37.7	100.00

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 377.31 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. Koerber J, Goodman D, Barnes JL, Grimm JW. The dopamine D2 antagonist eticlopride accelerates extinction and delays reacquisition of food self-administration in rats. Behav Pharmacol. 2013 Dec;24(8):633-9. doi: 10.1097/FBP.0000000000000002. PMID: 24113080; PMCID: PMC3896390. 2. Stiles L, Zheng Y, Darlington CL, Smith PF. The effects of the D2 dopamine receptor antagonist, eticlopride, on attention following bilateral vestibular deafferentation in the rat. Neurosci Lett. 2012 Jan 11;506(2):193-7. doi: 10.1016/j.neulet.2011.11.003. Epub 2011 Nov 6. PMID: 22094383.

In vitro protocol:

TBD

In vivo protocol:

1: Kumar V, Bonifazi A, Ellenberger MP, Keck TM, Pommier E, Rais R, Slusher BS, Gardner E, You ZB, Xi ZX, Newman AH. Highly Selective Dopamine D(3) Receptor (D(3)R) Antagonists and Partial Agonists Based on Eticlopride and the D(3)R Crystal Structure: New Leads for Opioid Dependence Treatment. J Med Chem. 2016 Aug 10. [Epub ahead of print] PubMed PMID: 27508895. 2: Soto PL, Grandy DK, Hursh SR, Katz JL. Erratum to: behavioral economics of food reinforcement and the effects of prefeeding, extinction, and eticlopride in dopamine D₂ receptor mutant mice. Psychopharmacology (Berl). 2015 May;232(9):1669. doi: 10.1007/s00213-015-3918-x. PubMed PMID: 25814138. 3: Koerber J, Goodman D, Barnes JL, Grimm JW. The dopamine D2 antagonist eticlopride accelerates extinction and delays reacquisition of food self-administration in rats. Behav Pharmacol. 2013 Dec;24(8):633-9. doi: 10.1097/FBP.0000000000000002. PubMed PMID: 24113080; PubMed Central PMCID: PMC3896390. 4: Rogers RD, Wong A, McKinnon C, Winstanley CA. Systemic administration of 8-OH-DPAT and eticlopride, but not SCH23390, alters loss-chasing behavior in the rat. Neuropsychopharmacology. 2013 May;38(6):1094-104. doi: 10.1038/npp.2013.8. Epub 2013 Jan 7. PubMed PMID: 23303072; PubMed Central PMCID: PMC3629409. 5: Stiles L, Zheng Y, Darlington CL, Smith PF. The effects of the D2 dopamine receptor antagonist, eticlopride, on attention following bilateral vestibular deafferentation in the rat. Neurosci Lett. 2012 Jan 11;506(2):193-7. doi: 10.1016/j.neulet.2011.11.003. Epub 2011 Nov 6. PubMed PMID: 22094383. 6: Obiol-Pardo C, López L, Pastor M, Selent J. Progress in the structural prediction of G protein-coupled receptors: D3 receptor in complex with eticlopride. Proteins. 2011 Jun;79(6):1695-703. doi: 10.1002/prot.23021. Epub 2011 Apr 12. PubMed PMID: 21491496. 7: Soto PL, Grandy DK, Hursh SR, Katz JL. Behavioral economics of food reinforcement and the effects of prefeeding, extinction, and eticlopride in dopamine D2 receptor mutant mice. Psychopharmacology (Berl). 2011 Jun;215(4):775-84. doi: 10.1007/s00213-011-2173-z. Epub 2011 Feb 2. Erratum in: Psychopharmacology (Berl). 2015 May;232(9):1669. PubMed PMID: 21287342; PubMed Central PMCID: PMC3981201. 8: Martelle JL, Nader MA. A review of the discovery, pharmacological characterization, and behavioral effects of the dopamine D2-like receptor antagonist eticlopride. CNS Neurosci Ther. 2008 Fall;14(3):248-62. doi: 10.1111/j.1755-5949.2008.00047.x. Review. PubMed PMID: 18801115; PubMed Central PMCID: PMC2753830. 9: Claytor R, Lile JA, Nader MA. The effects of eticlopride and the selective D3-antagonist PNU 99194-A on food- and cocaine-maintained responding in rhesus monkeys. Pharmacol Biochem Behav. 2006 Mar;83(3):456-64. Epub 2006 May 2. PubMed PMID: 16631246. 10: Blokland A, Sik A, Lieben C. Evaluation of DOI, 8-OH-DPAT, eticlopride and amphetamine on impulsive responding in a reaction time task in rats. Behav Pharmacol. 2005 Mar;16(2):93-100. PubMed PMID: 15767844. 11: Brown RW, Thompson KN, Click IA, Best RA, Thacker SK, Perna MK. The effects of eticlopride on Morris water task performance in male and female rats neonatally treated with quinpirole. Psychopharmacology (Berl). 2005 Jul;180(2):234-40. Epub 2005 Feb 5. PubMed PMID: 15696328. 12: Areola OO, Jadhav AL. Responsiveness of extracellular dopamine in the nucleus accumbens to systemic quinpirole and eticlopride is modulated by low-level lead exposure. Environ Toxicol Pharmacol. 2005 Feb;19(2):323-8. doi: 10.1016/j.etap.2004.08.009. PubMed PMID: 21783492. 13: Schenk S, Gittings D. Effects of SCH 23390 and eticlopride on cocaine-seeking produced by cocaine and WIN 35,428 in rats. Psychopharmacology (Berl). 2003 Jul;168(1-2):118-23. Epub 2002 Nov 5. PubMed PMID: 12420155. 14: Harrison AA, Gasparini F, Markou A. Nicotine potentiation of brain stimulation reward reversed by DH beta E and SCH 23390, but not by eticlopride, LY 314582 or MPEP in rats. Psychopharmacology (Berl). 2002 Feb;160(1):56-66. Epub 2001 Dec 18. PubMed PMID: 11862374. 15: Areola OO, Jadhav AL. Low-level lead exposure modulates effects of quinpirole and eticlopride on response rates in a fixed-interval schedule. Pharmacol Biochem Behav. 2001 May-Jun;69(1-2):151-6. PubMed PMID: 11420080. 16: Adams AC, Keefe KA. Degree of immediate early gene induction in striatum by eticlopride determines sensitivity to N-methyl-D-aspartate receptor blockade. Brain Res. 2000 Dec 8;885(2):201-7. PubMed PMID: 11102574. 17: Brown RW, Bardo MT, Mace DD, Phillips SB, Kraemer PJ. D-amphetamine facilitation of morris water task performance is blocked by eticlopride and correlated with increased dopamine synthesis in the prefrontal cortex. Behav Brain Res. 2000 Sep;114(1-2):135-43. PubMed PMID: 10996054. 18: Bernstein SN, Beninger RJ. Turning in rats following intraaccumbens shell injections of amphetamine or eticlopride. Pharmacol Biochem Behav. 2000 Feb;65(2):203-7. PubMed PMID: 10672970. 19: Keefe KA, Adams AC. Differential effects of N-methyl-D-aspartate receptor blockade on eticlopride-induced immediate early gene expression in the medial and lateral striatum. J Pharmacol Exp Ther. 1998 Dec;287(3):1076-83. PubMed PMID: 9864295. 20: Fowler SC, Liou JR. Haloperidol, raclopride, and eticlopride induce microcatalepsy during operant performance in rats, but clozapine and SCH 23390 do not. Psychopharmacology (Berl). 1998 Nov;140(1):81-90. PubMed PMID: 9862406.