L-AP5 (L-APV; L-2-Amino-5-phosphonovaleric acid) is an NMDA antagonist that is more potent than the isomer D-AP5.

Physicochemical Properties

Molecular Formula	C5H12NO5P
Molecular Weight	197.126242637634
Exact Mass	197.045
CAS #	79055-67-7
Related CAS #	DL-AP5;76326-31-3;D-AP5;79055-68-8
PubChem CID	1617110
Appearance	Typically exists as solid at room temperature
Density	1.5±0.1 g/cm3
Boiling Point	482.1±55.0 °C at 760 mmHg
Flash Point	245.4±31.5 °C
Vapour Pressure	0.0±2.6 mmHg at 25°C
Index of Refraction	1.536
LogP	-2.32
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	5
Heavy Atom Count	12
Complexity	200
Defined Atom Stereocenter Count	1
SMILES	C(CP(O)(O)=O)C[C@H](N)C(=O)O
InChi Key	VOROEQBFPPIACJ-BYPYZUCNSA-N
InChi Code	InChI=1S/C5H12NO5P/c6-4(5(7)8)2-1-3-12(9,10)11/h4H,1-3,6H2,(H,7,8)(H2,9,10,11)/t4-/m0/s1
Chemical Name	(2S)-2-amino-5-phosphonopentanoic acid
Synonyms	L-AP5; 79055-67-7; (S)-2-amino-5-phosphonopentanoic acid; 5-phosphono-L-norvaline; (2S)-2-amino-5-phosphonopentanoic acid; CHEMBL71898; (S)-2-amino-5-phosphonopentanoicacid; L(+)-2-Amino-5-phosphonovaleric 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

Targets	NMDA Receptor
ln Vitro	The separate optical enantiomers of 2-amino-5-phosphonovalerate (APV) and 2-amino-4-phosphonobutyrate (APB) have been tested for their ability to modify amino acid-induced and synaptic excitation of cat spinal neurones. D-(-)-APV was a highly potent and selective antagonist of amino acid-induced and synaptic excitation. Polysynaptic excitation was more susceptible to antagonism by D-APV than was monosynaptic excitation. It was considered likely that the depression of synaptic excitation by D-APV was due to the blockade of an excitatory amino acid transmitter acting at N-methyl-D-aspartate (NMDA) receptors. L-(+)-APV showed a relatively weak amino acid and synaptic blocking activity, which was similar in character to that of D-APV, and which may have been due to a slight residuum of the D isomer in the sample of the L form used. D-(-)-APB was a weak and relatively non-selective antagonist of amino acid-induced responses. In contrast, L-(+)-APB either had no effect or, at higher concentrations, enhanced these responses. Both isomers depressed synaptic responses in a proportion of the cells tested, the L form being the more potent isomer in producing this effect. Monosynaptic and polysynaptic excitations were both susceptible to this type of action. The depression of synaptic excitation by D-APB may have been due in some cases to the blockade of an excitatory amino acid transmitter. However, it is unlikely that the synaptic depressant action of L-APB is due to this mechanism.[1]
References	[1]. Davies and Watkins (1982) Actions of D and L forms of 2-amino-5-phosphonovalerate and 2-amino-4-phosphonobutyrate in the cat spinal cord. Brain Res. 235 378.

Solubility Data

Solubility (In Vitro)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

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	5.0728 mL	25.3640 mL	50.7279 mL
	5 mM	1.0146 mL	5.0728 mL	10.1456 mL
	10 mM	0.5073 mL	2.5364 mL	5.0728 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.