G013
R(+)-Baclofen hydrochloride
solid
Synonym(s):
Arbaclofen hydrochloride, R(+)-β-(Aminomethyl)-4-chlorobenzenepropanoic acid hydrochloride, STX209
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About This Item
Empirical Formula (Hill Notation):
C10H12ClNO2 · HCl
CAS Number:
Molecular Weight:
250.12
NACRES:
NA.32
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
form
solid
Quality Level
optical activity
[α]28/D +3.8°, c = 0.9 in methanol(lit.)
storage condition
desiccated
color
white
solubility
DMSO: >20 mg/mL, H2O: 26 mg/mL (Solutions may be stored for several weeks at 4 °C.)
SMILES string
Cl[H].NC[C@H](CC(O)=O)c1ccc(Cl)cc1
InChI
1S/C10H12ClNO2.ClH/c11-9-3-1-7(2-4-9)8(6-12)5-10(13)14;/h1-4,8H,5-6,12H2,(H,13,14);1H/t8-;/m0./s1
InChI key
WMNUVYYLMCMHLU-QRPNPIFTSA-N
Gene Information
human ... GABBR1(2550)
mouse ... GABBR1(54393)
rat ... GABBR1(81657)
Application
R(+)-Baclofen hydrochloride has been used as a GABAB receptor agonist to study its effects on M43068-induced antinociception in rat models. It has also been used as a GABAB receptor agonist to study its effects on amphetamine-induced behavior and neurochemical responses in rat striatum.
Biochem/physiol Actions
Baclofen is a derivative of γ-aminobutyric acid (GABA) and acts as a 4-aminobutanoic acid receptor (GABAB) agonist. It interacts stereospecifically with the GABA receptor and exhibits antispastic effects.Baclofen shows therapeutic effects against paroxysmal pain of trigeminal neuralgia and spinal spasticity. R(+)-Baclofen is a more active enantiomer.
Other Notes
Same enantiomer as R(−)-baclofen free base.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Yuriko Watanabe et al.
European journal of pharmacology, 837, 88-95 (2018-08-08)
The nucleus accumbens contains delta-opioid receptors that may decrease inhibitory neurotransmission. As GABAB receptors inhibit dopamine release, decrease in activation of GABAB receptors may be a mediator of delta-opioid receptor-induced accumbal dopamine efflux. If so, accumbal dopamine efflux induced by
Synthesis of both enantiomers of baclofen using (R)-and (S)-N-phenylpantolactam as chiral auxiliaries
Camps P, et al.
Tetrahedron Asymmetry, 15(13) (2004)
Xia Li et al.
Neuropharmacology, 97, 357-364 (2015-05-24)
GABAB (γ-aminobutyric acid B) receptors may be a therapeutic target for anxiety disorders. Here we characterized the effects of the GABAB receptor positive allosteric modulator (PAM) BHF177 on conditioned and unconditioned physiological responses to threat in the light-enhanced startle (LES)