L-Cysteinesulfinic acid is a potent metabotropic glutamate receptor (mGluRs) agonist for mGluR1, mGluR5, mGluR2, mGluR4, mGluR6 and mGluR8, with pEC50 of 3.92, 4.6, 3.9, 2.7, 4.0, respectively. 3.94.

Physicochemical Properties

Molecular Formula	C3H7NO4S
Molecular Weight	153.15698
Exact Mass	153.01
CAS #	1115-65-7
Related CAS #	L-Cysteinesulfinic acid monohydrate;207121-48-0
PubChem CID	1549098
Appearance	White to off-white solid powder
Density	1.828g/cm3
Boiling Point	492.8ºC at 760mmHg
Melting Point	>130°C (dec.) (lit.)
Flash Point	251.8ºC
Vapour Pressure	4.68E-11mmHg at 25°C
Index of Refraction	1.673
LogP	0.186
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	3
Heavy Atom Count	9
Complexity	136
Defined Atom Stereocenter Count	1
SMILES	C([C@@H](C(=O)O)N)S(=O)O
InChi Key	ADVPTQAUNPRNPO-REOHCLBHSA-N
InChi Code	InChI=1S/C3H7NO4S/c4-2(3(5)6)1-9(7)8/h2H,1,4H2,(H,5,6)(H,7,8)/t2-/m0/s1
Chemical Name	(2R)-2-amino-3-sulfinopropanoic acid
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	The endogenous agonist of metabotropic receptors, L-cysteine sulfinic acid, increases the activity of phospholipase D (PLD). Endogenous agonist L-CSA binds to metabotropic excitatory amino acid (EAA) receptors that are connected to PLD. PLD-coupled receptors are preferentially activated by L-CSA. Hippocampal slices' PLD activity was significantly increased by 1 mM L-CSA, but L-glutamic acid, L-aspartic acid, and L-HCA had no effect at 1 mM. Rat hippocampal slices treated with L-CSA showed a dose-dependent increase in PLD activity with an EC50 of about 500 uM in the presence of iGluR antagonists. The PLD response elicited by 1 mM L-CSA did not significantly decrease in the presence of 1 uM tetrodotoxin, suggesting that the reaction was independent of the L-CSA-induced increase in cell firing [1].
References	[1]. L-homocysteine sulfinic acid and other acidic homocysteine derivatives are potent and selective metabotropic glutamate receptor agonists. J Pharmacol Exp Ther. 2003 Apr;305(1):131-42. [2]. L-cysteine sulfinic acid as an endogenous agonist of a novel metabotropic receptor coupled to stimulation of phospholipase D activity.
Additional Infomation	3-sulfino-L-alanine is the organosulfinic acid arising from oxidation of the sulfhydryl group of L-cysteine. It has a role as a metabotropic glutamate receptor agonist, a human metabolite, an Escherichia coli metabolite and a mouse metabolite. It is an organosulfinic acid and a S-substituted L-cysteine. It is a conjugate acid of a 3-sulfino-L-alanine(1-). It is a tautomer of a L-cysteine-S-dioxide. L-Cysteinesulfinic acid has been reported in Homo sapiens, Euglena gracilis, and other organisms with data available. See also: 3-Sulfinoalanine (annotation moved to).

Solubility Data

Solubility (In Vitro)

H2O : ~125 mg/mL (~816.14 mM)

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	6.5291 mL	32.6456 mL	65.2912 mL
	5 mM	1.3058 mL	6.5291 mL	13.0582 mL
	10 mM	0.6529 mL	3.2646 mL	6.5291 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.