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G013

Sigma-Aldrich

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:
63701-55-3
Molecular Weight:
250.12
MDL number:
MFCD00078579
UNSPSC Code:
12352200
PubChem Substance ID:
24895006
NACRES:
NA.32

form

solid

Quality Level

100

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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis of both enantiomers of baclofen using (R)-and (S)-N-phenylpantolactam as chiral auxiliaries
Camps P, et al.
Tetrahedron Asymmetry, 15(13) (2004)
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
Reagan L Pennock et al.
The Journal of physiology, 592(19), 4247-4256 (2014-08-03)
It has recently been shown that dynorphin A (Dyn A), an endogenous agonist of the κ-opioid receptor (KOR), directly inhibits proopiomelanocortin (POMC) neurons in the hypothalamus through activation of G-protein-coupled inwardly rectifying K(+) channels (GIRKs). This effect has been proposed
Intracerebral Baclofen Administration Decreases Amphetamine-Induced Behavior and Neuropeptide Gene Expression in the Striatum
Wenxia Z, et al.
Neuropsychopharmacology, 880?890-880?890 (2004)
An efficient synthesis of (R)-and (S)-baclofen via desymmetrization
Ji L, et al.
Tetrahedron Letters, 50(45), 6166-6168 (2009)
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