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A8054

D(−)-2-Amino-5-phosphonopentanoic acid

NMDA receptor antagonist

Synonym(s):

D(−)-AP-5, D(−)-APV, D-2-Amino-5-phosphonovaleric acid

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About This Item

Empirical Formula (Hill Notation):
C5H12NO5P
CAS Number:
79055-68-8
Molecular Weight:
197.13
NACRES:
NA.26
PubChem Substance ID:
24891311
UNSPSC Code:
12352106
MDL number:
MFCD00078839
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Quality Level

100

assay

≥98% (TLC)

form

powder

optical purity

optical purity: ≥90% (HPLC, Marfey′s reagent)

technique(s)

ligand binding assay: suitable

color

white

mp

245-246 °C

SMILES string

N[C@H](CCCP(O)(O)=O)C(O)=O

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-/m1/s1

InChI key

VOROEQBFPPIACJ-SCSAIBSYSA-N

Gene Information

mouse ... Grin2a(14811)
rat ... Grik1(29559), Grin2a(24409), Grin2b(24410), Grin2c(24411), Grin2d(24412)

Application

D(-)-2-Amino-5-phosphonopentanoic acid has been used to pretreat BNST (bed nucleus of the stria terminalis) in order to block the induction of anxiety by ORX-A (orexin-A) into the BNST.

Biochem/physiol Actions

Anticonvulsant; potent and selective N-methyl-D-aspartate (NMDA) receptor antagonist; active enantiomer of 2-amino-5-phosphonopentanoic acid.
NMDA antagonists have muscle relaxation property and are known to offer neuron protection against brain damage induced by ischemia. 2-Amino-5-phosphonopentanoic acid has been proved to block the iontophoresis induced depolarization of NMDA.

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This Item
A6553H5877G1001
D(−)-2-Amino-5-phosphonopentanoic acid NMDA receptor antagonist

Sigma-Aldrich

A8054

D(−)-2-Amino-5-phosphonopentanoic acid

DL-2-Amino-5-phosphonovaleric acid lithium salt ~95%

Sigma-Aldrich

A6553

DL-2-Amino-5-phosphonovaleric acid lithium salt

cis-4-Hydroxy-D-proline

Sigma-Aldrich

H5877

cis-4-Hydroxy-D-proline

D-Glutamic acid ≥99% (TLC)

Sigma-Aldrich

G1001

D-Glutamic acid

form

powder

form

powder

form

powder

form

powder

technique(s)

ligand binding assay: suitable

technique(s)

ligand binding assay: suitable

technique(s)

ligand binding assay: suitable

technique(s)

ligand binding assay: suitable

assay

≥98% (TLC)

assay

~95%

assay

≥98% (TLC)

assay

≥99% (TLC)

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

200

color

white

color

white to off-white

color

white

color

white to off-white

mp

245-246 °C

mp

-

mp

243 °C (dec.) (lit.)

mp

200-202 °C (subl.) (lit.)

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000532594
0000532592
0000532578
0000532594
0000532592

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Related Content

Product Information Sheet - A8054

Product Information Sheet

Synaptic Plasticity and Learning: Selective Impairment of Learning in
Rats and Blockade of Long-Term Potentiation in viva by the
IV-Methyl-D-Aspartate Receptor Antagonist AP5
R. G. M. Morris
The Journal of Neuroscience, 9(9), 3040-3057 (1989)
Paola Conti et al.
European journal of medicinal chemistry, 42(8), 1059-1068 (2007-03-10)
Twelve novel conformationally constrained homologues of glutamic acid have been synthesized and pharmacologically characterized at ionotropic glutamate receptors (iGluRs). Synthesis of the target compounds involved 1,3-dipolar cycloaddition of nitrile oxides to suitable dipolarophiles. The structure to the compounds has been
Daniela Gandolfi et al.
Frontiers in cellular neuroscience, 11, 184-184 (2017-07-14)
The induction of long-term potentiation and depression (LTP and LTD) is thought to trigger gene expression and protein synthesis, leading to consolidation of synaptic and neuronal changes. However, while LTP and LTD have been proposed to play important roles for
View All Related Papers

Global Trade Item Number

SKUGTIN
A8054-1MG04061826055762
A8054-5MG04061833391112
A8054-10MG04061833391105

Questions

1–3 of 3 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

  3. Could 2-Amino-5-phosphonopentanoic acid potentially serve as a positive control in traumatic brain injury research using an adult zebrafish model?

    1 answer

    1. Yes, D(−)-2-Amino-5-phosphonopentanoic acid is an NMDA receptor antagonist that can serve as a positive control in traumatic brain injury research.

      Helpful?

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