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Merck

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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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)

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
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
042M4605V
066K4603
084H39003
084H39002
084H39001

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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)
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
Luminal administration ex vivo of a live Lactobacillus species moderates mouse jejunal motility within minutes.
Wang B, et al.
Faseb Journal, 24(10), 4078-4088 (2010)
H Hasuo et al.
Neuroscience letters, 86(1), 77-81 (1988-03-21)
Phaclofen has recently been described as an antagonist to baclofen at both peripheral and central receptors. We have applied phaclofen in known concentrations to an isolated rat brain slice preparation containing the septal nuclei. Our data demonstrate that phaclofen antagonizes
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