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Baclofen structure
Baclofen structure

Baclofen

Iupac Name:4-amino-3-(4-chlorophenyl)butanoic acid
CAS No.: 1134-47-0
Molecular Weight:213.661
Modify Date.: 2022-11-05 04:33
Introduction: Odorless or practically odorless white to off-white crystalline powder. View more+
1. Names and Identifiers
1.1 Name
Baclofen
1.2 Synonyms

)-Baclofen)-Β-(Aminomethyl)-4-chlorobenzenepropanoic acid (R,S)-Baclofen 4-Amino-3-(4-chlorophenyl)butanoic acid 4-Amino-3-(4-chlorophenyl)butyric Acid 4-Amino-3-(p-chlorophenyl)butyric acid Atrofen b-(Aminomethyl)-4-chlorobenzenepropanoic Acid b-(Aminomethyl)-p-chlorohydrocinnamic Acid baclon benzenepropanoic acid, b-(aminomethyl)-4-chloro- Benzenepropanoic acid, β-(aminomethyl)-4-chloro- Benzenepropanoic acid, Β-(aminomethyl)-4-chloro-(9CI) Benzenepropanoic acid, Β-(aminomethyl)-4-chloro-, (±)- CIBA Ba 34647 Clofen DL-4-Amino-3-p-chlorophenylbutanoic acid DL-Baclofen EINECS 214-486-9 Hydrocinnamic acid, Β-(aminomethyl)-p-chloro- Hydrocinnamic acid, β-(aminomethyl)-p-chloro- (7CI, 8CI) Lioresa Lioresal MFCD00055143 Z1YR DG&1VQKemstro β-(4-Chlorophenyl)-γ-aminobutyric acid β-p-Chlorophenyl-GABA

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1.3 CAS No.
1134-47-0
1.4 CID
2284
1.5 EINECS(EC#)
214-486-9
1.6 Molecular Formula
C10H12ClNO2 (isomer)
1.7 Inchi
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)
1.8 InChIkey
KPYSYYIEGFHWSV-UHFFFAOYSA-N
1.9 Canonical Smiles
C1=CC(=CC=C1C(CC(=O)O)CN)Cl
1.10 Isomers Smiles
C1=CC(=CC=C1C(CC(=O)O)CN)Cl
2. Properties
2.1 Density
1.285
2.1 Melting point
208-210oC
2.1 Boiling point
364.3oC at 760 mmHg
2.1 Refractive index
1.576
2.1 Flash Point
174.1oC
2.1 Precise Quality
213.05600
2.1 PSA
63.32000
2.1 logP
2.55730
2.1 Solubility
1 M HCl: 50?mg/mL
2.2 Appearance
white to very faintly yellow solid
2.3 Storage
Keep Cold.
2.4 Color/Form
Powder
2.5 Physical
PHYSICAL DESCRIPTION: Odorless or practically odorless white to off-white crystalline powder. (NTP, 1992)
2.6 pKa
pKa 3.87±0.1(H2O) (Uncertain)
2.7 Water Solubility
1 M HCl: 50?mg/mL
2.8 StorageTemp
2-8°C
3. Use and Manufacturing
3.1 Definition
ChEBI: A monocarboxylic acid that is butanoic acid substituted by an amino group at position 4 and a 4-chlorophenyl group at position 3. It acts as a central nervous system depressant, GABA agonist and muscle relaxant.
3.2 General Description
Odorless or practically odorless white to off-white crystalline powder.
3.3 GHS Classification
Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 39 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H301 (87.18%): Toxic if swallowed [Danger Acute toxicity, oral]
H302 (12.82%): Harmful if swallowed [Warning Acute toxicity, oral]
H315 (71.79%): Causes skin irritation [Warning Skin corrosion/irritation]
H317 (69.23%): May cause an allergic skin reaction [Warning Sensitization, Skin]
H319 (71.79%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H334 (69.23%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]
H335 (69.23%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
H336 (12.82%): May cause drowsiness or dizziness [Warning Specific target organ toxicity, single exposure; Narcotic effects]
H360 (61.54%): May damage fertility or the unborn child [Danger Reproductive toxicity]
H361 (17.95%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P261, P264, P270, P271, P272, P280, P281, P285, P301+P310, P301+P312, P302+P352, P304+P340, P304+P341, P305+P351+P338, P308+P313, P312, P321, P330, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P403+P233, P405, and P501
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3.4 Usage
1. The product is a relaxant and antispasmodic agent acting on the skeletal muscle of spinal cord. Suitable for treating multiple-sclerosis bones spasms, spinal infection, degenerated muscle spasms; spinal cord trauma, and neoplastic muscle spasms.2. It is currently the most effective muscle relaxants with least side effects.
4. Safety and Handling
4.1 Symbol
GHS06;GHS08;
4.1 Hazard Codes
T
4.1 Signal Word
DANGER
4.1 Risk Statements
R61;R25;R36/37/38;R42/43
4.1 Safety Statements
S52;S22;S36/37/39;S45
4.1 Packing Group
III
4.1 Fire Hazard
Flash point data for Baclofen are not available. Baclofen is probably combustible.
4.2 Hazard Class
6.1(b)
4.2 Hazard Declaration
H301; H315; H317; H319; H334; H335; H360
4.2 RIDADR
UN 2811
4.2 Safety Profile
Poison by ingestion,subcutaneous and intravenous routes. Human systemiceffects by ingestion: blood pressure lowering, coma,muscle weakness, pulse rate decrease, respiratorydepression. When heated to decomposition it emits toxicfumes of Cl-
4.3 Caution Statement
Missing Phrase - N15.00950417-P201-P261-P280-P284-P308 + P313
4.3 WGK Germany
3
4.3 RTECS
MW5084200
4.3 Safety

Poison by ingestion, subcutaneous and intravenous routes. Human systemic effects by ingestion: blood pressure lowering, coma, muscle weakness, pulse rate decrease, respiratory depression. When heated to decomposition it emits toxic fumes of Cl and NOx. A muscle relaxant.
Safety Information of Baclofen (CAS NO.1134-47-0)
Hazard Codes:  T,Xn
Risk Statements: 61-25-36/37/38-42/43-20/21/22 
R61:May cause harm to the unborn child. 
R25 :Toxic if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R42/43:May cause sensitization by inhalation and skin contact. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 53-22-36/37/39-45-52-26 
S53:Avoid exposure - obtain special instructions before use. 
S22:Do not breathe dust. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S52:Not recommended for interior use on large surface areas. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: MW5084200
HazardClass: 6.1(b)
PackingGroup: III

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4.4 Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 571ug/kg (0.571mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA Annals of Pharmacotherpy. Vol. 27, Pg. 883, 1993.
man TDLo oral 4286ug/kg (4.286mg/kg) BEHAVIORAL: COMA

CARDIAC: PULSE RATE

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
American Journal of Emergency Medicine. Vol. 4, Pg. 552, 1986.
man TDLo oral 14mg/kg (14mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: COMA
Journal of Toxicology, Clinical Toxicology. Vol. 20, Pg. 59, 1983.
man TDLo oral 3429mg/kg (3429mg/kg) BEHAVIORAL: COMA

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY OBSTRUCTION
Journal of Toxicology, Clinical Toxicology. Vol. 32, Pg. 291, 1994.
man TDLo unreported 857ug/kg/2D-I (0.857mg/kg) BRAIN AND COVERINGS: CHANGES IN SURFACE EEG

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Italian Journal of Neurological Sciences. Vol. 12, Pg. 323, 1991.
mouse LD50 intravenous 31mg/kg (31mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 21, Pg. 2069, 1979.
mouse LD50 oral 200mg/kg (200mg/kg)   Drugs in Japan Vol. 6, Pg. 576, 1982.
mouse LD50 subcutaneous 103mg/kg (103mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 11, Pg. 181, 1980.
rat LD50 intravenous 78mg/kg (78mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 11, Pg. 181, 1980.
rat LD50 oral 145mg/kg (145mg/kg)   Drugs in Japan Vol. 6, Pg. 576, 1982.
rat LD50 subcutaneous 115mg/kg (115mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 11, Pg. 181, 1980.
women TDLo oral 8mg/kg (8mg/kg) CARDIAC: PULSE RATE

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Postgraduate Medical Journal. Vol. 57, Pg. 580, 1981.
women TDLo oral 9mg/kg (9mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Postgraduate Medical Journal. Vol. 56, Pg. 865, 1980.
women TDLo oral 18mg/kg (18mg/kg) BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Journal of Toxicology, Clinical Toxicology. Vol. 22, Pg. 11, 1984.
women TDLo parenteral 25ug/kg/2D-I (0.025mg/kg) SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

BEHAVIORAL: COMA
International Journal of Clinical Pharmacology, Therapy and Toxicology. Vol. 29, Pg. 274, 1991.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 3

Skin irritation, Category 2

Skin sensitization, Category 1

Eye irritation, Category 2

Respiratory sensitization, Category 1

Specific target organ toxicity \u2013 single exposure, Category 3

Reproductive toxicity, Category 1B

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H301 Toxic if swallowed

H315 Causes skin irritation

H317 May cause an allergic skin reaction

H319 Causes serious eye irritation

H334 May cause allergy or asthma symptoms or breathing difficulties if inhaled

H335 May cause respiratory irritation

H360 May damage fertility or the unborn child

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.

P272 Contaminated work clothing should not be allowed out of the workplace.

P284 [In case of inadequate ventilation] wear respiratory protection.

P271 Use only outdoors or in a well-ventilated area.

P201 Obtain special instructions before use.

P202 Do not handle until all safety precautions have been read and understood.

Response

P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026

P321 Specific treatment (see ... on this label).

P330 Rinse mouth.

P302+P352 IF ON SKIN: Wash with plenty of water/...

P332+P313 If skin irritation occurs: Get medical advice/attention.

P362+P364 Take off contaminated clothing and wash it before reuse.

P333+P313 If skin irritation or rash occurs: Get medical advice/attention.

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P337+P313 If eye irritation persists: Get medical advice/attention.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P342+P311 If experiencing respiratory symptoms: Call a POISON CENTER/doctor/...

P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.

P308+P313 IF exposed or concerned: Get medical advice/ attention.

Storage

P405 Store locked up.

P403+P233 Store in a well-ventilated place. Keep container tightly closed.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

9. Other Information
9.0 Merck
14,937
9.1 Production process
Chlorobenzaldehyde and ethyl acetoacetate are condensed into chlorobenzene methylene-bis-ethyl acetoacetate. Heat and hydrolyze to obtain chlorophenyl glutaric acid. Use acetic anhydride for dehydration and cyclization to obtain chlorophenyl glutaric anhydride. And then perform amination reaction by concentrated aqueous ammonia to generate chlorophenyl glutaric acid imide. The open the ring, degrade to obtain the final product.
9.2 Pharmacokinetics
After oral administration, concentration in plasma reaches a peak in about 1.9h. There is large fluctuation in plasma concentration with the maximum concentration/minimum concentration × 100%: 188-439%. The total clearance rate is about 175mL.min-1, and the apparent renal clearance crisp is the same as that of muscle. The plasma protein binding rate is 35%. The excretion rate of kidney prototype drug is 65%, which is consistent with healthy results. Because renal excretion is the major route of elimination, patients with renal impairment should pay attention to adjust the dose.
9.3 Indications
This product is an antispasmodic drug. It inhibits the transmission in spinal cord of mono-synapse multiple synapse. The mechanism is inhibiting the release of excitatory amino acid glutamate and aspartate through stimulating GABA receptor. Thus reduce the increased limbs muscle tension caused by spinal cord lesions, multiple sclerosis, and spinal cord injury. It can be used for treatment of muscle spasms caused by brain and spinal cord diseases or injuries.
9.4 Precautions
1. Among the overdose behavior, the depression of central nervous system is the most prominent. Severe poisoning manifestations include seizures, coma, respiratory depression and muscle hypotonia associated with loss of reflexes of the limbs, and also hypotension and low blood pressure sometimes. Strategies for emergence treatment of acute poisoning include respiratory support, gastric lavage, and diuretic. However, there is no special antidote reported. There are some reports that seizures and myoclonic seizures appeared in some patients appear during the recovery period. Epileptic seizure can be treated by diazepam or clonazepam, although these drugs can cause extension of the duration of unconsciousness. Patients of cardiovascular disease should be carefully observed for 1 week to monitor delayed tachycardia and hypertension.
2. Patients who are allergic to the drug, suffering Parkinson's disease, spasms, and the women who are in the first three months of pregnancy are not allowed for using.
3. Patients of hypertension, peptic ulcer disease, cerebrovascular disease and respiratory, issue liver and kidney dysfunction, who have a history of seizures or convulsions, accompanied by mental disorders, schizophrenia or confusion, pregnant and lactating women, drivers or operator of machine should use with caution.
4. Epileptic patients should be controlled of the attack of epilepsy when applying this drug. Also they should do EEG monitoring.
5. Gradually reduce the dosage before the withdrawal, to prevent rebound phenomenon.
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9.5 Side effects
The main side effects mainly happen at the beginning of treatment when the dose increases too fast, when overdose happens and for elderly patients. It is mainly mild transient symptoms, Patients with historical mental illness and elderly patients with cerebral vascular disease may suffer from an even more severe adverse reaction. During the beginning of treatment, there are often some side effects such as daytime sedation, drowsiness and nausea.
9.6 Dosage and usage
Oral: adult, Initial amount of 5mg per time, tid, then every increase taking this amount every 3d until it reaches the appropriate dose 30~75mg/d. Take this in 3 times. The dose should not exceed 80 mg/d except in special cases. Gradually reduce the dosage before withdrawal; For children, the initial amount should be 0.3mg/(kg.d), and the maintenance dose should be 0.75~2mg/(kg.d). For children under 10 years-old, the maximum dose should be 2.5mg /(kg.d). The recommended daily amount for maintenance therapy: 1 to 2 years-old, 10~20mg, 2~10 years-old: 30~60mg (maximum 70mg), take it with meal or with milk.
9.7 Chemical Properties
White powder. Melting point: 206-208 °C. Dissolve using hot water, the aqueous solution was neutral, almost insoluble in alcohol, ether, acetone and other organic solvents, easily soluble in acidic, alkaline aqueous solution. The melting point of Chlorobenzene aminobutyric acid hydrochloride: 179-181 °C.
9.8 Uses
1. The product is a relaxant and antispasmodic agent acting on the skeletal muscle of spinal cord. Suitable for treating multiple-sclerosis bones spasms, spinal infection, degenerated muscle spasms; spinal cord trauma, and neoplastic muscle spasms.
2. It is currently the most effective muscle relaxants with least side effects.
9.9 Category
toxic substances
9.10 Toxicity grading
highly toxic
9.11 Acute toxicity
Oral-rat LD50; 145 mg/kg; Oral-Mouse LD50: 200 mg/kg.
9.12 Flammability and hazardous characteristics
Combustible, Burning yields toxic chloride fumes and nitrogen oxides; Patients takes with side effects: low blood pressure, pulse rate decreases, muscle weakness.
9.13 Chemical Properties
Off-White Solid
9.14 Storage Characteristics
ventilation, low-temperature and dry; and Separate from food raw materials for storage.
9.15 Uses
Specific GABA-B receptor agonist. Muscle relaxant (skeletal)
9.16 Definition
ChEBI: A monocarboxylic acid that is butanoic acid substituted by an amino group at position 4 and a 4-chlorophenyl group at position 3. It acts as a central nervous system depressant, GABA agonist and muscle relaxant.
9.17 Brand name
Kemstro (Schwarz Pharma); Lioresal (Medtronic); Lioresal (Novartis).
9.18 Extinguishing agent
Dry powder, foam, sand, carbon dioxide, water spray.
9.19 General Description
Odorless or practically odorless white to off-white crystalline powder.
9.20 Air & Water Reactions
Insoluble in water.
9.21 Reactivity Profile
Baclofen is an amine. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.
9.22 Health Hazard
SYMPTOMS: Symptoms of exposure to Baclofen via ingestion may include drowsiness, insomnia, dizziness, weakness, mental confusion, nausea, constipation, anorexia, urinary retention, impotence, nystagmus, diplopia and incoordination. Ingestion may lead to cholinergic effects and lassitude. It may also lead to ataxia. Other symptoms due to ingestion may include impaired renal function, fatigue, headache, hypotension, urinary frequency, rash, pruritis, ankle edema, excessive perspiration, weight gain, nasal congestion, and rarely, euphoria, excitement, depression, hallucinations, paresthesia, muscle pain, tinnitus, slurred speech, tremor, rigidity, dystonia, blurred vision, strabismus, miosis, mydriasis, dysarthia, epileptic seizure, dyspnea, palpitation, chest pain, syncope, dryness of the mouth, taste disorder, abdominal pain, vomiting, diarrhea, blood in the stools, enuresis, dysuria, inability to ejaculate, nocturia and hematuria. Overexposure through ingestion may result in seizures, and coma with respiratory depression. Aspiration pneumonia is a frequent complication of coma with respiratory depression. Other symptoms due to overdosage may include vomiting, muscular hypotonia, drowsiness, and accommodation disorders. Cyanosis has been reported. Chronic ingestion may result in drowsiness, depression, weakness, anxiety, ataxia, headaches, blurred vision, gastric upset and pruritic skin rashes characterized by urticaria or erythematous macular eruptions. Sudden withdrawal after chronic ingestion may cause auditory and visual hallucinations, anxiety and tachycardia. Seizures may also occur after sudden withdrawal. Abuse may lead to drug dependence.
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9.23 Fire Hazard
Flash point data for Baclofen are not available. Baclofen is probably combustible.
9.24 Biological Activity
Selective GABA B receptor agonist. Skeletal muscle relaxant.
9.25 Usage
Selective GABA-b receptor agonist
10. Computational chemical data
  • Molecular Weight: 213.661g/mol
  • Molecular Formula: C10H12ClNO2
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 213.0556563
  • Monoisotopic Mass: 213.0556563
  • Complexity: 191
  • Rotatable Bond Count: 4
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Topological Polar Surface Area: 63.3
  • Heavy Atom Count: 14
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADccByMAAEAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAHgIQCAAADQLBmCQwCIBAAgCIAiDSCAACAAAgBQAIiIEAAogIIDKBkxGAYAAkkAAIiAe8yOCOhAAAAAAAAAAIAAAAAAAAAAAAAAAAAA==
11. Question & Answer
  • Baclofen is a commonly used pharmaceutical ingredient with a wide range of applications in the medical field. So, how is Baclofen extracted and prepared? The extraction and preparation process of Bacl..
  • Baclofen is a muscle relaxant for skeletal muscles used to treat muscle spasms, spinal cord injuries, or multiple sclerosis. It was approved for medical use in the United States in 1977 and can be use..
  • Baclofen is a medication used to treat various conditions such as spinal cord tumors, multiple sclerosis, meningitis, and skeletal muscle spasms caused by cerebrovascular disease or head trauma. It h..
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