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P118

Sigma-Aldrich

Phaclofen

solid

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Synonym(s):
3-Amino-2-(4-chlorophenyl)propanephosphonic acid
Empirical Formula (Hill Notation):
C9H13ClNO3P
CAS Number:
Molecular Weight:
249.63
MDL number:
PubChem Substance ID:
NACRES:
NA.32

form

solid

Quality Level

impurities

≥97% (NMR)

color

white

solubility

0.1 M HCl: 13.3 mg/mL
methanol: 19.3 mg/mL
DMSO: insoluble

SMILES string

NCC(CP(O)(O)=O)c1ccc(Cl)cc1

InChI

1S/C9H13ClNO3P/c10-9-3-1-7(2-4-9)8(5-11)6-15(12,13)14/h1-4,8H,5-6,11H2,(H2,12,13,14)

InChI key

VSGNGLJPOGUDON-UHFFFAOYSA-N

Gene Information

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This Item
A6566S166B0200000
Phaclofen solid

P118

Phaclofen

2-Hydroxysaclofen ≥98% (TLC), solid

A6566

2-Hydroxysaclofen

Saclofen solid

S166

Saclofen

Baclofen European Pharmacopoeia (EP) Reference Standard

B0200000

Baclofen

Gene Information

human ... GABBR1(2550), GABBR2(9568)

Gene Information

human ... GABBR1(2550), GABBR2(9568)

Gene Information

human ... GABBR1(2550), GABBR2(9568)
mouse ... GABBR1(54393), GABBR2(242425)
rat ... GABBR1(81657), GABBR2(83633)

Gene Information

human ... GABBR1(2550), GABBR2(9568)

impurities

≥97% (NMR)

impurities

-

impurities

-

impurities

-

color

white

color

white

color

white

color

-

solubility

0.1 M HCl: 13.3 mg/mL

solubility

H2O: 1 mg/mL, 0.1 M HCl: 1.2 mg/mL, methanol: 1.4 mg/mL, DMSO: 28 mg/mL, 0.1 M NaOH: 9.5 mg/mL

solubility

0.1 M NaOH: 20 mg/mL

solubility

-

General description

Phaclofen is a phosphonic acid derivative of baclofen.

Application

Phaclofen has been used to block GABAB receptor.

Biochem/physiol Actions

Phaclofen plays a vital role in identifying the physiological importance of central and peripheral bicuculline-insensitive receptors with which GABA and (−) baclofen interact. Phaclofen acts as a GABAB receptor antagonist. Phaclofen has an ability to reversibly block the late, bicuculline resistant, K+ dependent inhibitory postsynaptic potential (IPSP) logged in projection cells of the cat and rat dorsal lateral geniculate nucleus and in rat hippocampal CA1 pyramidal neurons.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Baclofen European Pharmacopoeia (EP) Reference Standard

B0200000

Baclofen

Aconitine ≥95% (HPLC), crystalline

Sigma-Aldrich

A8001

Aconitine

Effat Ramshini et al.
International journal of preventive medicine, 4(2), 158-164 (2013-04-02)
There is only little information about the effects of GABA receptors agonist and antagonist on morphine self-administration. Present study was designed to assess role of GABAB receptors in the regulation of morphine-reinforced self-administration. THIS STUDY WAS PERFORMED IN FOUR GROUPS
Kazuo Kunisawa et al.
European journal of pharmacology, 796, 122-130 (2016-12-13)
GABA mediated neuronal system regulates hippocampus-dependent memory and stress responses by controlling plasticity and neuronal excitability. Here, we demonstrate that betaine ameliorates water-immersion restraint stress (WIRS)-induced memory impairments. This improvement was inhibited by a betaine/GABA transporter-1 (GABA transporter-2: GAT2) inhibitor
The GABAB antagonist phaclofen inhibits the late K+-dependent IPSP in cat and rat thalamic and hippocampal neurones
Soltesz I, et al.
Brain Research, 448(2), 351-354 (1988)
P Dutar et al.
Nature, 332(6160), 156-158 (1988-03-10)
The role of GABA in synaptic transmission in the mammalian central nervous system is more firmly established than for any other neurotransmitter. With virtually every neuron studied, the synaptic action of GABA is mediated by bicuculline-sensitive GABAA receptors which selectively
Phaclofen: a peripheral and central baclofen antagonist
Kerr D I, et al.
Brain Research, 405(1), 150-154 (1987)

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