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4-amino-3-(4-chlorophenyl)butanoic acid
Conditions | Yield |
---|---|
With hydrogenchloride In water at 130℃; for 24h; Sealed tube; | 97% |
4-amino-3-(4-chlorophenyl)butanoic acid
Conditions | Yield |
---|---|
With sodium L-ascorbate; fluorescein free acid In aq. phosphate buffer for 0.5h; pH=7.4; Irradiation; | 87% |
4-(4-chlorophenyl)pyrrolidin-2-one
4-amino-3-(4-chlorophenyl)butanoic acid
Conditions | Yield |
---|---|
With hydrogenchloride; water In water for 16h; Reflux; | 81% |
With hydrogenchloride for 2h; Heating; | 54% |
Conditions | Yield |
---|---|
With sodium sulfamate; sodium hypobromide at -5 - 55℃; for 2.16667h; | 79.4% |
4-amino-3-(4-chlorophenyl)butanoic acid
Conditions | Yield |
---|---|
With ammonia; hydrogen In water at 25 - 30℃; for 6h; | 70% |
ethyl 4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-(4-chlorophenyl)butanoate
4-amino-3-(4-chlorophenyl)butanoic acid
Conditions | Yield |
---|---|
With hydrogenchloride; hydrazine hydrate In ethanol Heating; | 58% |
4-amino-3-(4-chlorophenyl)butanoic acid
Conditions | Yield |
---|---|
With ammonium hydroxide In methanol at 60℃; for 2h; pH=6.9 - 7; | 41% |
ethyl 3-(4-chlorophenyl)-3-hydroxybutanoate
4-amino-3-(4-chlorophenyl)butanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 1.) p-toluenesulfonic acid, 2.) 10percent NaOH / 1.) toluene, reflux, 3 h, 2.) reflux, 2 h 2: 37 percent / 1.) N-bromosuccinimide, 2.) NH3 / 1.) CCl4, reflux, 48 h, 2.) THF, 3 h 3: 16 percent / NH3 / tetrahydrofuran / 3 h 4: 65 percent / 1 M NH4OH / 1 h / 70 °C 5: 59 percent / H2, Raney nickel W-5 / ethanol / 16 h / 3040 Torr / Ambient temperature 6: 54 percent / 6 M HCl / 2 h / Heating View Scheme | |
Multi-step reaction with 6 steps 1: 1.) p-toluenesulfonic acid, 2.) 10percent NaOH / 1.) toluene, reflux, 3 h, 2.) reflux, 2 h 2: 37 percent / N-bromosuccinimide / CCl4 / 48 h / Heating 3: 16 percent / NH3 / tetrahydrofuran / 3 h 4: 65 percent / 1 M NH4OH / 1 h / 70 °C 5: 59 percent / H2, Raney nickel W-5 / ethanol / 16 h / 3040 Torr / Ambient temperature 6: 54 percent / 6 M HCl / 2 h / Heating View Scheme |
(E)-3-(4-chlorophenyl)but-2-enoic acid
4-amino-3-(4-chlorophenyl)butanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 37 percent / 1.) N-bromosuccinimide, 2.) NH3 / 1.) CCl4, reflux, 48 h, 2.) THF, 3 h 2: 16 percent / NH3 / tetrahydrofuran / 3 h 3: 65 percent / 1 M NH4OH / 1 h / 70 °C 4: 59 percent / H2, Raney nickel W-5 / ethanol / 16 h / 3040 Torr / Ambient temperature 5: 54 percent / 6 M HCl / 2 h / Heating View Scheme | |
Multi-step reaction with 5 steps 1: 37 percent / N-bromosuccinimide / CCl4 / 48 h / Heating 2: 16 percent / NH3 / tetrahydrofuran / 3 h 3: 65 percent / 1 M NH4OH / 1 h / 70 °C 4: 59 percent / H2, Raney nickel W-5 / ethanol / 16 h / 3040 Torr / Ambient temperature 5: 54 percent / 6 M HCl / 2 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 240 g / Zn / benzene / Heating 2: 1.) p-toluenesulfonic acid, 2.) 10percent NaOH / 1.) toluene, reflux, 3 h, 2.) reflux, 2 h 3: 37 percent / 1.) N-bromosuccinimide, 2.) NH3 / 1.) CCl4, reflux, 48 h, 2.) THF, 3 h 4: 16 percent / NH3 / tetrahydrofuran / 3 h 5: 65 percent / 1 M NH4OH / 1 h / 70 °C 6: 59 percent / H2, Raney nickel W-5 / ethanol / 16 h / 3040 Torr / Ambient temperature 7: 54 percent / 6 M HCl / 2 h / Heating View Scheme | |
Multi-step reaction with 7 steps 1: 240 g / Zn / benzene / Heating 2: 1.) p-toluenesulfonic acid, 2.) 10percent NaOH / 1.) toluene, reflux, 3 h, 2.) reflux, 2 h 3: 37 percent / N-bromosuccinimide / CCl4 / 48 h / Heating 4: 16 percent / NH3 / tetrahydrofuran / 3 h 5: 65 percent / 1 M NH4OH / 1 h / 70 °C 6: 59 percent / H2, Raney nickel W-5 / ethanol / 16 h / 3040 Torr / Ambient temperature 7: 54 percent / 6 M HCl / 2 h / Heating View Scheme |
1. Introduction of Baclofen
Baclofen is one kind of white powder or white to very faintly yellow solid. The IUPAC Name of this chemical is 4-Amino-3-(4-chlorophenyl)butanoic acid. Its Classification Code is Central Nervous System Agents ; Drug / Therapeutic Agent ; GABA Agents ; GABA agonists ; Human Data ; Muscle relaxants, central ; Neuromuscular Agents ; Neurotransmitter Agents ; Peripheral Nervous System Agents ; Relaxant [muscle]. The Product Categories of this chemical is Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts ; Active Pharmaceutical Ingredients ; Intermediates & Fine Chemicals ; Pharmaceuticals ; GABA/Glycine receptor ; GABA.
2. Properties of Baclofen
Physical properties about Baclofen are:
(1)Polar Surface Area: 29.54 Å2; (2)Index of Refraction: 1.576; (3)Molar Refractivity: 55.06 cm3; (4)Molar Volume: 166.2 cm3; (5)Surface Tension: 53 dyne/cm; (6)Density of Baclofen: 1.285 g/cm3; (7)Flash Point: 174.1 °C; (8)Enthalpy of Vaporization: 64.41 kJ/mol; (9)Boiling Point: 364.3 °C at 760 mmHg; (10)Vapour Pressure: 6.01E-06 mmHg at 25°C.
3. Structure Descriptors of Baclofen
(1)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);
(2)InChIKey: InChIKey=KPYSYYIEGFHWSV-UHFFFAOYSA-N;
(3)Smiles: c1cc(ccc1C(CC(=O)O)CN)Cl.
4. Toxicity of Baclofen
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. |
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
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.
6. Uses of Baclofen
Baclofen can be used as Specific GABA-B receptor agonist. Muscle relaxant (skeletal). It is primarily used to treat spasticity and is in the early research stages for use for the treatment of alcoholism. In addition, research has shown baclofen to be effective in the treatment of alcohol dependence and withdrawal, by inhibiting both withdrawal symptoms and cravings.
7. Production of Baclofen
You can condense the chlorobenzaldehyde with ethyl acetoacetate to get the chloro benzylidene-double-ethyl acetoacetate. Then you can get the for chlorinated phenyl glutaric acid after the chloro benzylidene-double-ethyl acetoacetate hydrolysis. Glutaric acid imide chlorophenyl, the last open-loop degradation on chlorobenzene aminobutyric acid then concentrated ammonia amination generate. Its final open-loop, the degradation of specific methods of operation are as follows: 42.25gβ-(p-chlorophenyl) glutaric acid imide was added under stirring to the aqueous solution containing 8.32 g of sodium hydroxide in 200ml. The mixture is heated at 50 ° C for 10min, cooled to 10-15 ° C, 200ml aqueous solution containing 40.9g of sodium hydroxide was added dropwise, 20min, add 38.8g bromide, stirred at 20-25 ° C 8H, carefully neutralized with concentrated hydrochloric acid and the reaction mixturewas adjusted to pH 7, and then settle out fine β-(p-chlorophenyl)-γ-amino - butyric acid was crystallized and then recrystallized from water, m.p. 206-208 ° C.