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Merck
CN

P118

Phaclofen

solid

Synonym(s):

3-Amino-2-(4-chlorophenyl)propanephosphonic acid

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About This Item

Empirical Formula (Hill Notation):
C9H13ClNO3P
CAS Number:
114012-12-3
Molecular Weight:
249.63
NACRES:
NA.32
PubChem Substance ID:
24278189
UNSPSC Code:
12352200
MDL number:
MFCD00069328

Key Documents

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Product Name

Phaclofen, solid

InChI key

VSGNGLJPOGUDON-UHFFFAOYSA-N

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)

form

solid

impurities

≥97% (NMR)

color

white

solubility

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

Quality Level

100

Gene Information

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

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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.

General description

Phaclofen is a phosphonic acid derivative of baclofen.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

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
0000137056
0000134950
042M4605V
066K4603
084H39003

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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
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)
Phaclofen: a peripheral and central baclofen antagonist
Kerr D I, et al.
Brain Research, 405(1), 150-154 (1987)
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