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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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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
0000137056
0000134950
042M4605V
066K4603
084H39003

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D I Kerr et al.
Brain research, 405(1), 150-154 (1987-03-03)
Phaclofen, the phosphonic acid derivative of baclofen, reversibly antagonized the depression of the cholinergic twitch response of the guinea pig ileum and distal colon by either baclofen or GABA. When administered microelectrophoretically, phaclofen reversibly blocked the presumed presynaptic reduction by
Makoto Nishiyama et al.
Frontiers in synaptic neuroscience, 2, 22-22 (2010-01-01)
GABAergic interneuronal network activities in the hippocampus control a variety of neural functions, including learning and memory, by regulating θ and γ oscillations. How these GABAergic activities at pre- and postsynaptic sites of hippocampal CA1 pyramidal cells differentially contribute to
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)
Mohammad Nasehi et al.
Brain research bulletin, 130, 101-106 (2017-01-24)
Activation of the GABA
Christof Geigerseder et al.
Reproductive biology and endocrinology : RB&E, 2, 13-13 (2004-03-26)
The neurotransmitter gamma-aminobutyric acid (GABA) and subtypes of GABA receptors were recently identified in adult testes. Since adult Leydig cells possess both the GABA biosynthetic enzyme glutamate decarboxylase (GAD), as well as GABA(A) and GABA(B) receptors, it is possible that
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