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1078-21-3

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Factory bulk supply high quality nootropic Phenibut raw powder Phenibut
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4-Amino-3-phenylbutanoic acid
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4-Amino-3-phenylbutyric acid CAS:1078-21-3 Phenibut
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1078-21-3 Usage

Description

Phenibut, also known as fenibut, phenigamma, and beta-phenyl-gamma-aminobutyric acid, is a derivative of the neurotransmitter GABA. It was developed in Russia,and there it has been used clinically since the 1960s to treat anxiety and related conditions,including insomnia(Lapin,2001). Phenibut has anxiolytic properties and is commonlycompared to benzodiazepines and baclofen.Structurally,phenibut issimilar to GABA, with the addition of the phenyl ring. This allows thecompound to more easily cross the blood-brain barrier, but also changesits activity profile (Shulgina,1986). Scientific studies demonstrate that phenibut can be safely used to treat anxiety, depression,epilepsy, speech disorders, and insomnia.

Uses

4-amino-3-phenylbutanoic acid (cas# 1078-21-3) is a GABAA receptor agonist, used for treatment of disorders influenced by dysfunction of pancreatic β cells and also used in combination with other agents.

Preparation

Phenibut was synthesized by Perekalin and his associates at the Department of Organic Chemistry of the Herzen Pedagogic Institute in St. Petersburg, the Russian Federation. In initial publications phenibut was known as phenigamma (Lapin, 2001, V. V. Perekalin, 1954).Fenibut synthesis: from benzoyl chloride and ethyl acetoacetate as raw materials, through condensation and hydrolysis of ethyl benzoyl acetate, and then condensation of benzaldehyde and nitromethane to generate trans-nitrostyrene, and then the two are combined. Micheal addition, the adduct is then catalytically hydrogenated with Raney nickel, and finally hydrolyzed in concentrated hydrochloric acid to produce phenibate.Synthesis of Phenibut (16) and Baclofen (17).

Application

Phenibut is an anxiolytic and nootropic drug, discovered in the Soviet Union used to treat several psychiatric disorders. It can be used in the treatment of anxiety, depression, asthenia, post-traumatic stress disorder, stuttering, and vestibular disorders.

Safety Profile

Moderately toxic by intraperitoneal route. Human systemic effects by ingestion: somnolence, hallucinations, distorted perception. Used as a mood elevator and tranquilizer. When heated to decomposition it emits toxic fumes of NOx.

Regulatory Status

USA - Phenibut is still an uncontrolled substance in the United States, and it is legal to sell and possess phenibut. It has not been approved for clinical use in the United States. Europe - Unscheduled. It is not regulated by the European Medicines Agency. However, some nootropic substances such as piracetam are available only on prescription in some European Union countries and are freely available in others. Russia - Phenibut is a licensed prescription medication used for a variety of conditions including anxiety, insomnia, post-traumatic stress disorders, depression, stuttering, tics, attention deficit disorders, and vestibular disorders. Russian cosmonauts were reported to have been supplied with the substance to help relieve tension, anxiety and fear (Buckley 2006).
InChI:InChI=1/C10H13NO2.ClH/c11-7-9(6-10(12)13)8-4-2-1-3-5-8;/h1-5,9H,6-7,11H2,(H,12,13);1H

1078-21-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Amino-3-phenylbutyric acid hydrochloride

1.2 Other means of identification

Product number -
Other names fenigama

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1078-21-3 SDS

1078-21-3Synthetic route

4-nitro-3-phenylbutanoic acid
41441-41-2

4-nitro-3-phenylbutanoic acid

4-amino-3-phenylbutanoic acid
1078-21-3

4-amino-3-phenylbutanoic acid

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 60℃; under 45004.5 Torr;98%
4-(1,3-dioxoisoindolin-2-yl)-3-phenyl-N-(quinolin-8-yl)butanamide

4-(1,3-dioxoisoindolin-2-yl)-3-phenyl-N-(quinolin-8-yl)butanamide

4-amino-3-phenylbutanoic acid
1078-21-3

4-amino-3-phenylbutanoic acid

Conditions
ConditionsYield
With hydrogenchloride In water at 130℃; for 24h; Sealed tube;95%
2-oxo-4-phenyl-3-ethoxycarbonylpyrrolidine
52450-32-5

2-oxo-4-phenyl-3-ethoxycarbonylpyrrolidine

4-amino-3-phenylbutanoic acid
1078-21-3

4-amino-3-phenylbutanoic acid

Conditions
ConditionsYield
With hydrogenchloride
4-phenylpyrrolidin-2-one

4-phenylpyrrolidin-2-one

4-amino-3-phenylbutanoic acid
1078-21-3

4-amino-3-phenylbutanoic acid

Conditions
ConditionsYield
With hydrogenchloride Heating;
3-cyano-3-phenyl propionic acid
14387-18-9

3-cyano-3-phenyl propionic acid

4-amino-3-phenylbutanoic acid
1078-21-3

4-amino-3-phenylbutanoic acid

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In acetic acid under 15200 Torr;
(+-)-3-phenyl-glutaramic acid

(+-)-3-phenyl-glutaramic acid

4-amino-3-phenylbutanoic acid
1078-21-3

4-amino-3-phenylbutanoic acid

Conditions
ConditionsYield
With sodium hydroxide; sodium hypobromide
hydrogenchloride
7647-01-0

hydrogenchloride

3-phenyl-glutaric acid dihydrazide
72976-16-0

3-phenyl-glutaric acid dihydrazide

isopentyl nitrite
110-46-3

isopentyl nitrite

A

B

4-amino-3-phenylbutanoic acid
1078-21-3

4-amino-3-phenylbutanoic acid

Conditions
ConditionsYield
at 25℃; Kochen mit Bromwasserstoffsaeure;
benzyl alcohol

benzyl alcohol

4-amino-3-phenylbutanoic acid
1078-21-3

4-amino-3-phenylbutanoic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; sodium hypochlorite; potassium bromide / water; dichloromethane / 0.21 h / 0 °C
2.1: potassium tert-butylate / toluene; methanol / 0.17 h / 20 °C / 4500.45 Torr / Inert atmosphere
2.2: 0.11 h / 25 °C / 4500.45 Torr / Inert atmosphere
3.1: tetrabutyl ammonium fluoride / toluene; tetrahydrofuran / 1 h / 50 °C / 6000.6 Torr
4.1: lithium hydroxide; water / toluene / 1 h / 50 °C / 3750.38 Torr
5.1: hydrogen; palladium 10% on activated carbon / methanol / 60 °C / 45004.5 Torr
View Scheme
benzaldehyde
100-52-7

benzaldehyde

4-amino-3-phenylbutanoic acid
1078-21-3

4-amino-3-phenylbutanoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium tert-butylate / toluene; methanol / 0.17 h / 20 °C / 4500.45 Torr / Inert atmosphere
1.2: 0.11 h / 25 °C / 4500.45 Torr / Inert atmosphere
2.1: tetrabutyl ammonium fluoride / toluene; tetrahydrofuran / 1 h / 50 °C / 6000.6 Torr
3.1: lithium hydroxide; water / toluene / 1 h / 50 °C / 3750.38 Torr
4.1: hydrogen; palladium 10% on activated carbon / methanol / 60 °C / 45004.5 Torr
View Scheme
methyl cinnamate
103-26-4

methyl cinnamate

4-amino-3-phenylbutanoic acid
1078-21-3

4-amino-3-phenylbutanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetrabutyl ammonium fluoride / toluene; tetrahydrofuran / 1 h / 50 °C / 6000.6 Torr
2: lithium hydroxide; water / toluene / 1 h / 50 °C / 3750.38 Torr
3: hydrogen; palladium 10% on activated carbon / methanol / 60 °C / 45004.5 Torr
View Scheme
4-nitro-3-phenylbutanoic acid methyl ester
34687-03-1

4-nitro-3-phenylbutanoic acid methyl ester

4-amino-3-phenylbutanoic acid
1078-21-3

4-amino-3-phenylbutanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium hydroxide; water / toluene / 1 h / 50 °C / 3750.38 Torr
2: hydrogen; palladium 10% on activated carbon / methanol / 60 °C / 45004.5 Torr
View Scheme
4-amino-3-phenylbutanoic acid
1078-21-3

4-amino-3-phenylbutanoic acid

2-Fluorobenzaldehyde
446-52-6

2-Fluorobenzaldehyde

methyl 2,4-dioxopentanoate
20577-61-1

methyl 2,4-dioxopentanoate

4-[3-acetyl-2-(2-fluoro-phenyl)-4-hydroxy-5-oxo-2,5-dihydro-pyrrol-1-yl]-3-phenyl-butyric acid

4-[3-acetyl-2-(2-fluoro-phenyl)-4-hydroxy-5-oxo-2,5-dihydro-pyrrol-1-yl]-3-phenyl-butyric acid

Conditions
ConditionsYield
In ethanol; water at 20℃; for 12h; Condensation;78%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

4-amino-3-phenylbutanoic acid
1078-21-3

4-amino-3-phenylbutanoic acid

4-((tert-butoxycarbonyl)amino)-3-phenylbutanoic acid
189014-01-5

4-((tert-butoxycarbonyl)amino)-3-phenylbutanoic acid

Conditions
ConditionsYield
With sodium hydroxide In water; tert-butyl alcohol at 0 - 20℃;73%
4-amino-3-phenylbutanoic acid
1078-21-3

4-amino-3-phenylbutanoic acid

benzyl alcohol
100-51-6

benzyl alcohol

C17H19NO2*(x)ClH

C17H19NO2*(x)ClH

Conditions
ConditionsYield
With thionyl chloride at 0 - 20℃; for 16h;66%
4-amino-3-phenylbutanoic acid
1078-21-3

4-amino-3-phenylbutanoic acid

N,N'-diisopropyl-O-methylisourea
54648-79-2

N,N'-diisopropyl-O-methylisourea

C13H19NO2
129453-46-9

C13H19NO2

Conditions
ConditionsYield
In methanol for 120h; Ambient temperature;65%
phthalic anhydride
85-44-9

phthalic anhydride

4-amino-3-phenylbutanoic acid
1078-21-3

4-amino-3-phenylbutanoic acid

4-(1,3-dioxoisoindolin-2-yl)-3-phenylbutanoic acid

4-(1,3-dioxoisoindolin-2-yl)-3-phenylbutanoic acid

Conditions
ConditionsYield
In ethanol for 3h; Reflux;62%
4-amino-3-phenylbutanoic acid
1078-21-3

4-amino-3-phenylbutanoic acid

4-phenylpyrrolidin-2-one
1198-97-6

4-phenylpyrrolidin-2-one

Conditions
ConditionsYield
With potassium hydroxide
4-amino-3-phenylbutanoic acid
1078-21-3

4-amino-3-phenylbutanoic acid

(RS)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide
77472-70-9

(RS)-2-(2-oxo-4-phenylpyrrolidin-1-yl)acetamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium hydroxide / ethanol / 65 - 75 °C
2: ethanol / 65 - 75 °C
3: acetic acid / ethanol
4: Heating
View Scheme
4-amino-3-phenylbutanoic acid
1078-21-3

4-amino-3-phenylbutanoic acid

4-[(2-amino-2-oxoethyl)amino]-3-phenylbutanoic acid

4-[(2-amino-2-oxoethyl)amino]-3-phenylbutanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium hydroxide / ethanol / 65 - 75 °C
2: ethanol / 65 - 75 °C
3: acetic acid / ethanol
View Scheme
4-amino-3-phenylbutanoic acid
1078-21-3

4-amino-3-phenylbutanoic acid

4-[bis(2-amino-2-oxoethyl)amino]-3-phenylbutanoic acid sodium salt

4-[bis(2-amino-2-oxoethyl)amino]-3-phenylbutanoic acid sodium salt

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: potassium hydroxide / ethanol / 65 - 75 °C
2: ethanol / 65 - 75 °C
3: acetic acid / ethanol
4: sodium hydroxide / ethanol / 65 - 75 °C
5: ethanol / 65 - 75 °C
View Scheme
4-amino-3-phenylbutanoic acid
1078-21-3

4-amino-3-phenylbutanoic acid

C10H12NO2(1-)*K(1+)

C10H12NO2(1-)*K(1+)

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 65 - 75℃;
4-amino-3-phenylbutanoic acid
1078-21-3

4-amino-3-phenylbutanoic acid

C12H15N2O3(1-)*K(1+)

C12H15N2O3(1-)*K(1+)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium hydroxide / ethanol / 65 - 75 °C
2: ethanol / 65 - 75 °C
View Scheme
4-amino-3-phenylbutanoic acid
1078-21-3

4-amino-3-phenylbutanoic acid

C12H15N2O3(1-)*Na(1+)

C12H15N2O3(1-)*Na(1+)

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium hydroxide / ethanol / 65 - 75 °C
2: ethanol / 65 - 75 °C
3: acetic acid / ethanol
4: sodium hydroxide / ethanol / 65 - 75 °C
View Scheme
4-amino-3-phenylbutanoic acid
1078-21-3

4-amino-3-phenylbutanoic acid

N-(4-hydroxy-2-phenylbutyl)-2H-benzo[e][1,2,4]thiadiazine-3-carboxamide 1,1-dioxide

N-(4-hydroxy-2-phenylbutyl)-2H-benzo[e][1,2,4]thiadiazine-3-carboxamide 1,1-dioxide

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sodium hydroxide / water; tert-butyl alcohol / 0 - 20 °C
2.1: potassium carbonate / tetrahydrofuran / 0.25 h / 20 °C
2.2: 20 °C
3.1: hydrogenchloride / ethyl acetate / 3 h / 20 °C
4.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 20 °C
5.1: sodium hydroxide / 3 h / 20 °C
6.1: borane-THF / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere
View Scheme
4-amino-3-phenylbutanoic acid
1078-21-3

4-amino-3-phenylbutanoic acid

tert-butyl (3-amino-2-phenylpropyl)carbamate
437708-57-1

tert-butyl (3-amino-2-phenylpropyl)carbamate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ethanol / 3 h / Reflux
2: triethylamine; diphenyl phosphoryl azide / 1,4-dioxane / 100 °C
3: hydrazine hydrate / ethanol / 2 h / 80 °C
View Scheme
4-amino-3-phenylbutanoic acid
1078-21-3

4-amino-3-phenylbutanoic acid

tert-butyl (3-(1,1-dioxido-2H-benzo[e][1,2,4]thiadiazine-3-carboxamido)-2-phenylpropyl)carbamate

tert-butyl (3-(1,1-dioxido-2H-benzo[e][1,2,4]thiadiazine-3-carboxamido)-2-phenylpropyl)carbamate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: ethanol / 3 h / Reflux
2.1: triethylamine; diphenyl phosphoryl azide / 1,4-dioxane / 100 °C
3.1: hydrazine hydrate / ethanol / 2 h / 80 °C
4.1: sodium hydrogencarbonate / dichloromethane / 0.17 h / 20 °C
4.2: 1 h / 20 °C
View Scheme
4-amino-3-phenylbutanoic acid
1078-21-3

4-amino-3-phenylbutanoic acid

N-(3-amino-2-phenylpropyl)-2H-benzo[e][1,2,4]thiadiazine-3-carboxamide 1,1-dioxide hydrochloride

N-(3-amino-2-phenylpropyl)-2H-benzo[e][1,2,4]thiadiazine-3-carboxamide 1,1-dioxide hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: ethanol / 3 h / Reflux
2.1: triethylamine; diphenyl phosphoryl azide / 1,4-dioxane / 100 °C
3.1: hydrazine hydrate / ethanol / 2 h / 80 °C
4.1: sodium hydrogencarbonate / dichloromethane / 0.17 h / 20 °C
4.2: 1 h / 20 °C
5.1: hydrogenchloride / ethyl acetate / 2 h / 20 °C
View Scheme
4-amino-3-phenylbutanoic acid
1078-21-3

4-amino-3-phenylbutanoic acid

methyl 4-amino-3-phenylbutanoate hydrochloride
25271-46-9

methyl 4-amino-3-phenylbutanoate hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydroxide / water; tert-butyl alcohol / 0 - 20 °C
2.1: potassium carbonate / tetrahydrofuran / 0.25 h / 20 °C
2.2: 20 °C
3.1: hydrogenchloride / ethyl acetate / 3 h / 20 °C
View Scheme
4-amino-3-phenylbutanoic acid
1078-21-3

4-amino-3-phenylbutanoic acid

methyl 4-(1,1-dioxido-2H-benzo[e][1,2,4]thiadiazine-3-carboxamido)-3-phenylbutanoate

methyl 4-(1,1-dioxido-2H-benzo[e][1,2,4]thiadiazine-3-carboxamido)-3-phenylbutanoate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydroxide / water; tert-butyl alcohol / 0 - 20 °C
2.1: potassium carbonate / tetrahydrofuran / 0.25 h / 20 °C
2.2: 20 °C
3.1: hydrogenchloride / ethyl acetate / 3 h / 20 °C
4.1: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 20 °C
View Scheme
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