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A8054

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

NMDA receptor antagonist

Synonim(y):

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

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Informacje o tej pozycji

Wzór empiryczny (zapis Hilla):
C5H12NO5P
Numer CAS:
Masa cząsteczkowa:
197.13
NACRES:
NA.26
PubChem Substance ID:
UNSPSC Code:
12352106
MDL number:
Informacje o cenach i dostępności nie są obecnie dostępne.
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Quality Level

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

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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Ta pozycja
A6553H5877G1001
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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Klasa składowania

11 - Combustible Solids

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flash_point_c

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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
Jennifer N Gelinas et al.
Learning & memory (Cold Spring Harbor, N.Y.), 15(5), 281-289 (2008-04-29)
Activation of beta-adrenergic receptors (beta-ARs) enhances hippocampal memory consolidation and long-term potentiation (LTP), a likely mechanism for memory storage. One signaling pathway linked to beta-AR activation is the cAMP-PKA pathway. PKA is critical for the consolidation of hippocampal long-term memory



Numer pozycji handlu globalnego

SKUNUMER GTIN
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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