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A167

Sigma-Aldrich

D(−)-2-Amino-7-phosphonoheptanoic acid

solid

Synonym(s):

D-AP-7

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About This Item

Empirical Formula (Hill Notation):
C7H16NO5P
CAS Number:
81338-23-0
Molecular Weight:
225.18
MDL number:
MFCD00070086
UNSPSC Code:
12352200
PubChem Substance ID:
24278251

form

solid

color

white

solubility

H2O: soluble

SMILES string

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

Gene Information

human ... GRIN1(2902) , GRIN2A(2903) , GRIN2B(2904) , GRIN2C(2905) , GRIN2D(2906) , GRINA(2907)
rat ... Grin2a(24409) , Grin2b(24410) , Grin2c(24411) , Grin2d(24412)

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Biochem/physiol Actions

Selective NMDA glutamate receptor antagonist; anticonvulsant; active enantiomer of 2-amino-7-phosphonoheptanoic acid.

Caution

Hygroscopic. Store desiccated at RT.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P261 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Marina Prigol et al.
Chemico-biological interactions, 193(1), 65-70 (2011-05-31)
The present study investigated the role of the glutathione system in seizures induced by diphenyl diselenide (PhSe)(2) (50 mg/kg) in rat pups (post natal day, 12-14). Reduced glutathione (GSH) (300 nmol/site; i.c.v.), administered 20 min before (PhSe)(2), abolished the appearance
Daniele Cristina Aguiar et al.
Journal of neuroscience research, 87(11), 2418-2429 (2009-04-11)
Innate fear stimulus induces activation of neurons containing the neuronal nitric oxide synthase enzyme (nNOS) in defensive-related brain regions such as the dorsolateral periaqueductal gray (dlPAG). Intra-dlPAG administration of nitric oxide synthase (NOS) inhibitors and glutamate antagonists induce anxiolytic-like responses.
M Benveniste et al.
British journal of pharmacology, 104(1), 207-221 (1991-09-01)
1. The kinetics of action of 17 structurally related NMDA receptor competitive antagonists were measured under voltage clamp in mouse hippocampal neurones. Analysis of the response to rapid changes in antagonist concentration during constant application of agonist was used to
Luiz F S Souza-Pinto et al.
Pharmacology, biochemistry, and behavior, 87(2), 250-257 (2007-06-01)
It is well established that the most persistent sign of withdrawal from chronic benzodiazepine use in humans is anxiety. In contrast to other types of drugs of abuse, the emergence of this anxiety does not seem to be linked directly
Manoela V Fogaça et al.
Psychopharmacology, 226(3), 579-587 (2012-11-28)
The endocannabinoid and endovanniloid anandamide (AEA) exerts biphasic effects when injected into the dorsolateral periaqueductal grey (dlPAG) in rats submitted to threatening situations. Whereas lower doses of AEA induce anxiolytic-like effects by activating cannabinoid CB1 receptors, no effects are observed
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