ContaminantDB: Baclofen

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (4)XML

Record Information

Version

1.0

Creation Date

2009-07-05 02:43:46 UTC

Update Date

2026-05-14 16:24:31 UTC

Accession Number

CHEM002081

Identification

Common Name

Baclofen

Class

Small Molecule

Description

Baclofen is a gamma-amino-butyric acid (GABA) derivative used as a skeletal muscle relaxant. Baclofen stimulates GABA-B receptors leading to decreased frequency and amplitude of muscle spasms. It is especially useful in treating muscle spasticity associated with spinal cord injury. It appears to act primarily at the spinal cord level by inhibiting spinal polysynaptic afferent pathways and, to a lesser extent, monosynaptic afferent pathways.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Drug
GABA Agonist
Human Neurotoxin
Metabolite
Muscle Relaxant
Muscle Relaxant, Central
Muscle Relaxant, Skeletal
Neuromuscular Agent
Organic Compound
Organochloride
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+-)-Baclofen	ChEBI
4-Amino-3-(4-chlorophenyl)butyric acid	ChEBI
Baclofene	ChEBI
Baclofeno	ChEBI
Baclofenum	ChEBI
beta-(4-Chlorophenyl)gaba	ChEBI
beta-(Aminomethyl)-4-chlorobenzenepropanoic acid	ChEBI
beta-(Aminomethyl)-p-chlorohydrocinnamic acid	ChEBI
beta-(p-Chlorophenyl)-gamma-aminobutyric acid	ChEBI
DL-4-Amino-3-p-chlorophenylbutanoic acid	ChEBI
DL-Baclofen	ChEBI
gamma-Amino-beta-(p-chlorophenyl)butyric acid	ChEBI
Kemstro	Kegg
Lioresal	Kegg
4-Amino-3-(4-chlorophenyl)butyrate	Generator
b-(4-Chlorophenyl)gaba	Generator
Β-(4-chlorophenyl)gaba	Generator
b-(Aminomethyl)-4-chlorobenzenepropanoate	Generator
b-(Aminomethyl)-4-chlorobenzenepropanoic acid	Generator
beta-(Aminomethyl)-4-chlorobenzenepropanoate	Generator
Β-(aminomethyl)-4-chlorobenzenepropanoate	Generator
Β-(aminomethyl)-4-chlorobenzenepropanoic acid	Generator
b-(Aminomethyl)-p-chlorohydrocinnamate	Generator
b-(Aminomethyl)-p-chlorohydrocinnamic acid	Generator
beta-(Aminomethyl)-p-chlorohydrocinnamate	Generator
Β-(aminomethyl)-p-chlorohydrocinnamate	Generator
Β-(aminomethyl)-p-chlorohydrocinnamic acid	Generator
b-(p-Chlorophenyl)-g-aminobutyrate	Generator
b-(p-Chlorophenyl)-g-aminobutyric acid	Generator
beta-(p-Chlorophenyl)-gamma-aminobutyrate	Generator
Β-(p-chlorophenyl)-γ-aminobutyrate	Generator
Β-(p-chlorophenyl)-γ-aminobutyric acid	Generator
DL-4-Amino-3-p-chlorophenylbutanoate	Generator
g-Amino-b-(p-chlorophenyl)butyrate	Generator
g-Amino-b-(p-chlorophenyl)butyric acid	Generator
gamma-Amino-beta-(p-chlorophenyl)butyrate	Generator
Γ-amino-β-(p-chlorophenyl)butyrate	Generator
Γ-amino-β-(p-chlorophenyl)butyric acid	Generator
ASTA medica brand OF baclofen	MeSH, HMDB
Alphapharm brand OF baclofen	MeSH, HMDB
Ashbourne brand OF baclofen	MeSH, HMDB
Baclofen athena brand	MeSH, HMDB
Baclofen irex brand	MeSH, HMDB
Baclospas	MeSH, HMDB
Chlorophenyl gaba	MeSH, HMDB
Ciba geigy brand OF baclofen	MeSH, HMDB
Gen baclofen	MeSH, HMDB
GenBaclofen	MeSH, HMDB
Isis brand OF baclofen	MeSH, HMDB
PCP-GABA	MeSH, HMDB
AWD, baclofen	MeSH, HMDB
Athena brand OF baclofen	MeSH, HMDB
Atrofen	MeSH, HMDB
Baclofen apotex brand	MeSH, HMDB
Baclofen isis brand	MeSH, HMDB
Baclofen medtronic brand	MeSH, HMDB
Baclofen nu-pharm brand	MeSH, HMDB
Baclofen pharmascience brand	MeSH, HMDB
NuBaclo	MeSH, HMDB
PMS-Baclofen	MeSH, HMDB
PMSBaclofen	MeSH, HMDB
apo Baclofen	MeSH, HMDB
ApoBaclofen	MeSH, HMDB
Apotex brand OF baclofen	MeSH, HMDB
Baclofen awd	MeSH, HMDB
Baclofen ciba-geigy brand	MeSH, HMDB
Baclofen novartis brand	MeSH, HMDB
Baclofène irex	MeSH, HMDB
Baclofène-irex	MeSH, HMDB
BaclofèneIrex	MeSH, HMDB
CIBA-34,647-ba	MeSH, HMDB
Gen-baclofen	MeSH, HMDB
Irex brand OF baclofen	MeSH, HMDB
Lebic	MeSH, HMDB
Nu baclo	MeSH, HMDB
Nu-baclo	MeSH, HMDB
Nu-pharm brand OF baclofen	MeSH, HMDB
PMS Baclofen	MeSH, HMDB
apo-Baclofen	MeSH, HMDB
Baclofen alphapharm brand	MeSH, HMDB
Baclofen ashbourne brand	MeSH, HMDB
Baclophen	MeSH, HMDB
CIBA34,647ba	MeSH, HMDB
Ciba-geigy brand OF baclofen	MeSH, HMDB
Clofen	MeSH, HMDB
GABA, chlorophenyl	MeSH, HMDB
Genpharm	MeSH, HMDB
Medtronic brand OF baclofen	MeSH, HMDB
Novartis brand OF baclofen	MeSH, HMDB
Nu pharm brand OF baclofen	MeSH, HMDB
Pharmascience brand OF baclofen	MeSH, HMDB

Chemical Formula

C₁₀H₁₂ClNO₂

Average Molecular Mass

213.661 g/mol

Monoisotopic Mass

213.056 g/mol

CAS Registry Number

1134-47-0

IUPAC Name

4-amino-3-(4-chlorophenyl)butanoic acid

Traditional Name

baclofen

SMILES

NCC(CC(O)=O)C1=CC=C(Cl)C=C1

InChI Identifier

InChI=1S/C10H12ClNO2/c11-9-3-1-7(2-4-9)8(6-12)5-10(13)14/h1-4,8H,5-6,12H2,(H,13,14)

InChI Key

KPYSYYIEGFHWSV-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Gamma amino acids and derivatives

Alternative Parents

Substituents

Gamma amino acid or derivatives
3-phenylpropanoic-acid
Amino fatty acid
Chlorobenzene
Aralkylamine
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organohalogen compound
Organic nitrogen compound
Primary aliphatic amine
Organooxygen compound
Primary amine
Hydrocarbon derivative
Amine
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organochloride
Organonitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:2972 )
primary amino compound (CHEBI:2972 )
monochlorobenzenes (CHEBI:2972 )
gamma-amino acid (CHEBI:2972 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

GABA agonist

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Baclofen occurs as white to off-white crystals (7).

Experimental Properties

Property	Value
Melting Point	206-208°C
Boiling Point	Not Available
Solubility	2090 mg/L

Predicted Properties

Property	Value	Source
Water Solubility	0.71 g/L	ALOGPS
logP	-0.82	ALOGPS
logP	-0.78	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.89	ChemAxon
pKa (Strongest Basic)	9.79	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	54.83 m³·mol⁻¹	ChemAxon
Polarizability	21.13 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9600000000-6ae6d753213a9472b32c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0ff0-9720000000-6949ab5f0b56c63b916a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-03dr-0950000000-33d21cbb6740c1f1aee1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03di-1590000000-8a64733764308ba98f9a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0f6t-0900000000-6647c58db763b4df68a0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udi-0900000000-72d6d878c9c2f29d846a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-1900000000-18f69033596a03ee643a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-1900000000-997473c303f07afcdf4e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-0002-0900000000-d1da4625d180fe0af521	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03di-0190000000-bd0fff49defde62ed0fa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0ik9-0790000000-1a50b0b7f24aaaf6a87e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0ik9-0890000000-3f3794cee3f3ce674c85	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ot-0930000000-4c6fbeef09787ebe54c8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-016s-0900000000-904b104c639269bfe4f1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1900000000-62cafb0d9fec846e47b9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03xr-0690000000-4dd9b649eccb58c3cef0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03xr-0940000000-08d03c01d7cee16a2833	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ikl-1900000000-69e953c6f51f0939e70c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udj-0900000000-cd340e3600f88734f280	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-89fb1deb3a2cc738679c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0mmr-1900000000-62e1c901d161ea96465b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03xu-0920000000-6858869b9cb96b03630e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0gw0-1900000000-3a4e75e8e4356199aa50	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gx0-9800000000-bf4ef0f5f1c595bcb485	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000i-2900000000-963f049a4367a1d5a5f5	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Inhalation (8); ingestion (8); eye contact (8); dermal (8) Rapidly and almost completely absorbed from the GI tract.

Mechanism of Toxicity

Baclofen is a direct agonist at GABAB receptors. The precise mechanism of action of Baclofen is not fully known. It is capable of inhibiting both monosynaptic and polysynaptic reflexes at the spinal level, possibly by hyperpolarization of afferent terminals, although actions at supraspinal sites may also occur and contribute to its clinical effect.

Metabolism

~ 15% of the dose is metabolized in the liver, primarily by deamination. 70-80% of the dose is excreted unchanged or as metabolites in urine and the remainder is excreted in feces. Oral Baclofen is readily absorbed from the gastrointestinal tract. After oral administration, baclofen appears in the blodd within half an our. It is fairly distributed in most organs and body tissues. After oral administration of baclofen, about 85% is excreted unchanged in the urine and feces and the remainder is oxidatively dearninated in the liver to produce beta-(p-chlorophenyl)-gamma-hydroxybutyric acid as a major metabolite. (9). Route of Elimination: In a study using radiolabeled baclofen, approximately 85% of the dose was excreted unchanged in the urine and feces. Baclofen is excreted primarily by the kidney as unchanged drug; 70 - 80% of a dose appears in the urine as unchanged drug. The remainder is excreted as unchanged drug in the feces or as metabolites in the urine and feces. Half Life: 2.5-4 hours

Toxicity Values

LD50: 45 mg/kg (Intravenous, Mouse) (1) LD50: 78 mg/kg (Intravenous, Rat) (1)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the alleviation of signs and symptoms of spasticity resulting from multiple sclerosis, particularly for the relief of flexor spasms and concomitant pain, clonus, and muscular rigidity.

Minimum Risk Level

Not Available

Health Effects

Health effects include hypertonia, hyperthermia, formal thought disorder, psychosis, mania, mood disturbances, restlessness, and behavioral disturbances, tachycardia, seizures, tremors, autonomic dysfunction, hyperpyrexia, extreme muscle rigidity resembling neuroleptic malignant syndrome and rebound spasticity (5).

Symptoms

LD₅₀=45 mg/kg (male mice, IV); LD₅₀=78 mg/kg (male rat, IV)

Treatment

Treatment may involve "pumping" the stomach, inducing vomiting, administering an antidote, and providing supportive care. (6)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Baclofen

Chemspider ID

2197

ChEBI ID

2972

PubChem Compound ID

Not Available

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Wayne Levadoux, Denis Groleau, Michael Trani, Robert Lortie, “Streptomyces microorganism useful for the preparation of®-baclofen from the racemic mixture.” U.S. Patent US5843765, issued April, 1994.

MSDS

Link

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11772961

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=18682277

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18824012

Baclofen (CHEM002081)

Structure for CHEM002081: Baclofen