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A0664

Sigma-Aldrich

4-Aminobutylphosphonic acid

≥99%

Synonym(s):

P-(4-aminobutyl)-phosphonic acid

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About This Item

Empirical Formula (Hill Notation):
C4H12NO3P
CAS Number:
35622-27-6
Molecular Weight:
153.12
MDL number:
MFCD00063426
UNSPSC Code:
12352106
PubChem Substance ID:
24890444
NACRES:
NA.26

Quality Level

100

Assay

≥99%

form

powder

color

white

application(s)

detection

SMILES string

NCCCCP(O)(O)=O

InChI

1S/C4H12NO3P/c5-3-1-2-4-9(6,7)8/h1-5H2,(H2,6,7,8)

InChI key

IDPXFPYGZRMMKZ-UHFFFAOYSA-N

Biochem/physiol Actions

4-Aminobutylphosphonic acid, a GABA B receptor ligand, is used in studies on the regulation of prolactin (PRL) secretion and differential GABA receptor research.
4-aminobutylphosphonic acid, the phosphonic acid analogue of delta-aminovaleric acid, inhibits gamma-aminobutyric acid B (GABA-B receptor) binding without influencing either isoproterenol- or forskolin-stimulated cyclic AMP production.

Linkage

Analog of δ-aminovaleric acid

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - 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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Oktay Yildirim et al.
International journal of molecular sciences, 11(3), 1162-1179 (2010-05-19)
FePt nanoparticles (NPs) were assembled on aluminum oxide substrates, and their ferromagnetic properties were studied before and after thermal annealing. For the first time, phosph(on)ates were used as an adsorbate to form self-assembled monolayers (SAMs) on alumina to direct the
L S Wong et al.
Pharmacology, biochemistry, and behavior, 38(4), 829-835 (1991-04-01)
The application of 1.2 and 12.0 micrograms/side of the GABAA receptor agonist 3-aminopropane sulphonic acid bilaterally into the nucleus accumbens (Acb) of rats nonsignificantly depressed locomotor activity as assessed in automated Animex activity cages, while the highest dose (60 micrograms/side)
N G Ternan et al.
FEMS microbiology letters, 184(2), 237-240 (2000-03-14)
A strain of the yeast Kluyveromyces fragilis was screened for its ability to utilize a range of synthetic and natural organophosphonate compounds as the sole source of phosphorus, nitrogen or carbon. Only 4-aminobutylphosphonate was utilized as sole nitrogen source with
R M Woodward et al.
Molecular pharmacology, 43(4), 609-625 (1993-04-01)
Poly(A)+ RNA from mammalian retina expresses bicuculline/baclofen-insensitive gamma-aminobutyric acid (GABA) receptors in Xenopus oocytes with properties similar to those of homooligomeric GABA rho 1 receptors. The pharmacological profile of these rho-like receptors was extended by measuring sensitivities to various GABAA
R W Scherer et al.
Brain research bulletin, 21(3), 439-443 (1988-09-01)
Activation of GABAB receptors augments neurotransmitter-stimulated cyclic AMP accumulation while inhibiting forskolin-mediated second messenger production. Previous studies have revealed that GABAB receptors are associated with a pertussis toxin sensitive G protein, such as Gi. While such a linkage is consistent
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