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MedKoo Cat#: 414123 | Name: Eticlopride Free Base

Description:

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

Eticlopride 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. A great deal of research has utilized this drug to better understand central DA receptor function, the role of D2-like receptors in behavior, and the influence of blockade of these receptors on several preclinical animal models.

Chemical Structure

Eticlopride Free Base
Eticlopride Free Base
CAS#84226-12-0 (free base)

Theoretical Analysis

MedKoo Cat#: 414123

Name: Eticlopride Free Base

CAS#: 84226-12-0 (free base)

Chemical Formula: C17H25ClN2O3

Exact Mass: 340.1554

Molecular Weight: 340.85

Elemental Analysis: C, 59.91; H, 7.39; Cl, 10.40; N, 8.22; O, 14.08

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Related CAS #
97612-24-3 (HCl) 84226-12-0 (free base)
Synonym
Eticlopride Free Base; Eticloprida; Eticlopridum; FLB 131; FLB131; FLB-131;
IUPAC/Chemical Name
(-)-(S)-5-Chloro-3-ethyl-N-((1-ethyl-2-pyrrolidinyl)methyl)-6-methoxysalicylamide
InChi Key
AADCDMQTJNYOSS-LBPRGKRZSA-N
InChi Code
InChI=1S/C17H25ClN2O3/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)/t12-/m0/s1
SMILES Code
OC1=C(CC)C=C(Cl)C(OC)=C1C(NC[C@H]2N(CC)CCC2)=O
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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:
TBD
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/

Preparing Stock Solutions

The following data is based on the product molecular weight 340.85 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. 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. 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.
1: Highgate Q, Abadey AA, Schenk S. Repeated eticlopride administration increases dopamine D2 receptor expression and restores behavioral flexibility disrupted by methamphetamine exposure to male rats. Behav Brain Res. 2022 Oct 28;435:114064. doi: 10.1016/j.bbr.2022.114064. Epub 2022 Aug 18. PMID: 35987306. 2: 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. PMID: 18801115; PMCID: PMC2753830. 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. PMID: 24113080; PMCID: PMC3896390. 4: Shaik AB, Boateng CA, Battiti FO, Bonifazi A, Cao J, Chen L, Chitsazi R, Ravi S, Lee KH, Shi L, Newman AH. Structure Activity Relationships for a Series of Eticlopride-Based Dopamine D2/D3 Receptor Bitopic Ligands. J Med Chem. 2021 Oct 28;64(20):15313-15333. doi: 10.1021/acs.jmedchem.1c01353. Epub 2021 Oct 12. PMID: 34636551; PMCID: PMC9617622. 5: Rocca JF, Lister JG, Beninger RJ. Spiroperidol, but not eticlopride or aripiprazole, produces gradual increases in descent latencies in the bar test in rats. Behav Pharmacol. 2017 Feb;28(1):30-36. doi: 10.1097/FBP.0000000000000264. PMID: 27748674. 6: Ferrari F, Giuliani D. Effects of (-)eticlopride and 7-OH-DPAT on the tail- suspension test in mice. J Psychopharmacol. 1997;11(4):339-44. doi: 10.1177/026988119701100409. PMID: 9443522. 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. PMID: 21287342; PMCID: PMC3981201. 8: LaHoste GJ, Marshall JF. Chronic eticlopride and dopamine denervation induce equal nonadditive increases in striatal D2 receptor density: autoradiographic evidence against the dual mechanism hypothesis. Neuroscience. 1991;41(2-3):473-81. doi: 10.1016/0306-4522(91)90342-l. PMID: 1678501. 9: Hemby SE, Smith JE, Dworkin SI. The effects of eticlopride and naltrexone on responding maintained by food, cocaine, heroin and cocaine/heroin combinations in rats. J Pharmacol Exp Ther. 1996 Jun;277(3):1247-58. Erratum in: J Pharmacol Exp Ther 1996 Oct;279(1):442. PMID: 8667185. 10: 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. PMID: 23303072; PMCID: PMC3629409. 11: Köhler C, Hall H, Gawell L. Regional in vivo binding of the substituted benzamide [3H]eticlopride in the rat brain: evidence for selective labelling of dopamine receptors. Eur J Pharmacol. 1986 Jan 21;120(2):217-26. doi: 10.1016/0014-2999(86)90543-1. PMID: 3948920. 12: Giuliani D, Ferrari F. Involvement of dopamine receptors in the antipsychotic profile of (-) eticlopride. Physiol Behav. 1997 Apr;61(4):563-7. doi: 10.1016/s0031-9384(96)00503-3. PMID: 9108576. 13: 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. doi: 10.1016/j.pbb.2006.03.007. Epub 2006 May 2. PMID: 16631246. 14: 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):118-123. doi: 10.1007/s00213-002-1276-y. Epub 2002 Nov 5. PMID: 12420155. 15: 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 D3 Receptor (D3R) Antagonists and Partial Agonists Based on Eticlopride and the D3R Crystal Structure: New Leads for Opioid Dependence Treatment. J Med Chem. 2016 Aug 25;59(16):7634-50. doi: 10.1021/acs.jmedchem.6b00860. Epub 2016 Aug 10. PMID: 27508895; PMCID: PMC5001167. 16: Halldin C, Farde L, Högberg T, Hall H, Sedvall G. Carbon-11 labelling of eticlopride in two different positions--a selective high-affinity ligand for the study of dopamine D-2 receptors using PET. Int J Rad Appl Instrum A. 1990;41(7):669-74. doi: 10.1016/0883-2889(90)90082-r. PMID: 2170298. 17: Watanabe K, Fukumura T, Sasaki S, Maeda M, Takehara S. New fluorine- substituted analogue of eticlopride with high affinity toward dopamine D2 receptors. Chem Pharm Bull (Tokyo). 1991 Dec;39(12):3211-4. doi: 10.1248/cpb.39.3211. PMID: 1839971. 18: Vargo JM, Marshall JF. Reduced eticlopride-induced Fos expression in caudate-putamen and globus pallidus after unilateral frontal cortex injury: relation to neglect. Neuroscience. 1997 Feb;76(4):1083-95. doi: 10.1016/s0306-4522(96)00414-9. PMID: 9027868. 19: Hall H, Köhler C, Gawell L. Some in vitro receptor binding properties of [3H]eticlopride, a novel substituted benzamide, selective for dopamine-D2 receptors in the rat brain. Eur J Pharmacol. 1985 May 8;111(2):191-9. doi: 10.1016/0014-2999(85)90756-3. PMID: 4018125. 20: 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.