SYM2206 | CAS#173952-44-8 | AMPA receptor antagonist

MedKoo Cat#: 561343 | Name: SYM2206

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Description:

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

SYM2206 is a specific and non-competitive antagonist of AMPA receptors.

Chemical Structure

SYM2206

CAS#173952-44-8

Theoretical Analysis

MedKoo Cat#: 561343

Name: SYM2206

CAS#: 173952-44-8

Chemical Formula: C20H22N4O3

Exact Mass: 366.1692

Molecular Weight: 366.42

Elemental Analysis: C, 65.56; H, 6.05; N, 15.29; O, 13.10

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 340.00	2 Weeks
50mg	USD 1,125.00	2 Weeks

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Related CAS #

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Synonym

SYM2206; SYM 2206; SYM-2206;

IUPAC/Chemical Name

8-(4-Aminophenyl)-5-methyl-N-propyl-5H-[1,3]dioxolo[4,5-g]phthalazine-6-carboxamide

InChi Key

OFUDZKKOKPGXOH-UHFFFAOYSA-N

InChi Code

InChI=1S/C20H22N4O3/c1-3-8-22-20(25)24-12(2)15-9-17-18(27-11-26-17)10-16(15)19(23-24)13-4-6-14(21)7-5-13/h4-7,9-10,12H,3,8,11,21H2,1-2H3,(H,22,25)

SMILES Code

O=C(N1N=C(C2=CC=C(N)C=C2)C3=CC(OCO4)=C4C=C3C1C)NCCC

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:

SYM2206 is a selective antagonist of the AMPA (α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid) receptor. AMPA receptors are a subtype of ionotropic glutamate receptors that mediate fast synaptic transmission in the central nervous system. By blocking these receptors, SYM2206 affects glutamatergic neurotransmission and modulates various neurological processes and behaviors.

In vitro activity:

1. SYM2206, an AMPA receptor antagonist, was tested to explore its impact on estradiol (E2)-induced changes in pulsatile GnRH secretion in hypothalamic explants. SYM2206 did not prevent the reduction in GnRH interpulse interval (IPI) induced by E2, indicating that its effects are not mediated through AMPA receptors. This suggests that E2's modulation of GnRH IPI involves pathways distinct from those affected by SYM2206.

In vivo activity:

1. SYM2206, an AMPA receptor antagonist, was used to investigate its effects on theta and gamma oscillations in rodent primary motor cortex slices. SYM2206 was found to augment gamma oscillations while increasing theta power, highlighting its role in modulating these oscillatory activities. This compound contributed to understanding the pharmacological

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	272.92

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 366.42 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:

Johnson NW, Özkan M, Burgess AP, Prokic EJ, Wafford KA, O'Neill MJ, Greenhill SD, Stanford IM, Woodhall GL. Phase-amplitude coupled persistent theta and gamma oscillations in rat primary motor cortex in vitro. Neuropharmacology. 2017 Jun;119:141-156. doi: 10.1016/j.neuropharm.2017.04.009. Epub 2017 Apr 8. PMID: 28400257. Matagne V, Rasier G, Lebrethon MC, Gérard A, Bourguignon JP. Estradiol stimulation of pulsatile gonadotropin-releasing hormone secretion in vitro: correlation with perinatal exposure to sex steroids and induction of sexual precocity in vivo. Endocrinology. 2004 Jun;145(6):2775-83. doi: 10.1210/en.2003-1259. Epub 2004 Feb 26. PMID: 14988382. Ripka S, Riedel J, Neesse A, Griesmann H, Buchholz M, Ellenrieder V, Moeller F, Barth P, Gress TM, Michl P. Glutamate receptor GRIA3--target of CUX1 and mediator of tumor progression in pancreatic cancer. Neoplasia. 2010 Aug;12(8):659-67. doi: 10.1593/neo.10486. PMID: 20689760; PMCID: PMC2915410.

In vitro protocol:

Matagne V, Rasier G, Lebrethon MC, Gérard A, Bourguignon JP. Estradiol stimulation of pulsatile gonadotropin-releasing hormone secretion in vitro: correlation with perinatal exposure to sex steroids and induction of sexual precocity in vivo. Endocrinology. 2004 Jun;145(6):2775-83. doi: 10.1210/en.2003-1259. Epub 2004 Feb 26. PMID: 14988382.

In vivo protocol:

1: Johnson NW, Özkan M, Burgess AP, Prokic EJ, Wafford KA, O'Neill MJ, Greenhill SD, Stanford IM, Woodhall GL. Phase-amplitude coupled persistent theta and gamma oscillations in rat primary motor cortex in vitro. Neuropharmacology. 2017 Jun;119:141-156. doi: 10.1016/j.neuropharm.2017.04.009. Epub 2017 Apr 8. PubMed PMID: 28400257. 2: Ripka S, Riedel J, Neesse A, Griesmann H, Buchholz M, Ellenrieder V, Moeller F, Barth P, Gress TM, Michl P. Glutamate receptor GRIA3--target of CUX1 and mediator of tumor progression in pancreatic cancer. Neoplasia. 2010 Aug;12(8):659-67. PubMed PMID: 20689760; PubMed Central PMCID: PMC2915410. 3: Traub RD, Duncan R, Russell AJ, Baldeweg T, Tu Y, Cunningham MO, Whittington MA. Spatiotemporal patterns of electrocorticographic very fast oscillations (> 80 Hz) consistent with a network model based on electrical coupling between principal neurons. Epilepsia. 2010 Aug;51(8):1587-97. doi: 10.1111/j.1528-1167.2009.02420.x. Epub 2009 Dec 7. PubMed PMID: 20002152; PubMed Central PMCID: PMC2892641. 4: Welch NC, Lin W, Juranka PF, Morris CE, Stys PK. Traditional AMPA receptor antagonists partially block Na v1.6-mediated persistent current. Neuropharmacology. 2008 Dec;55(7):1165-71. doi: 10.1016/j.neuropharm.2008.07.015. Epub 2008 Jul 18. PubMed PMID: 18687344. 5: Redondo C, López-Toledano MA, Lobo MV, Gonzalo-Gobernado R, Reimers D, Herranz AS, Paíno CL, Bazán E. Kainic acid triggers oligodendrocyte precursor cell proliferation and neuronal differentiation from striatal neural stem cells. J Neurosci Res. 2007 May 1;85(6):1170-82. PubMed PMID: 17342781. 6: Shih YH, Chein YC, Wang JY, Fu YS. Ursolic acid protects hippocampal neurons against kainate-induced excitotoxicity in rats. Neurosci Lett. 2004 May 20;362(2):136-40. PubMed PMID: 15193771. 7: Matagne V, Rasier G, Lebrethon MC, Gérard A, Bourguignon JP. Estradiol stimulation of pulsatile gonadotropin-releasing hormone secretion in vitro: correlation with perinatal exposure to sex steroids and induction of sexual precocity in vivo. Endocrinology. 2004 Jun;145(6):2775-83. Epub 2004 Feb 26. PubMed PMID: 14988382. 8: Lowe G. Flash photolysis reveals a diversity of ionotropic glutamate receptors on the mitral cell somatodendritic membrane. J Neurophysiol. 2003 Sep;90(3):1737-46. Epub 2003 Apr 30. PubMed PMID: 12724365. 9: Ghersi C, Bonfanti A, Manzari B, Feligioni M, Raiteri M, Pittaluga A. Pharmacological heterogeneity of release-regulating presynaptic AMPA/kainate receptors in the rat brain: study with receptor antagonists. Neurochem Int. 2003 Mar;42(4):283-92. PubMed PMID: 12470701.