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2482-00-0

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  • High quality Agmatine sulfate with low price bulk in supply

    Cas No: 2482-00-0

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2482-00-0 Usage

General Uses

Neuroprotective, CNS studies, Autism and depression research Description: Agmatine Sulfate is a polyamine derived from L-arginine decarboxylation and is a known putative endogenous neurotransmitter at imidazoline receptors. Agmatine sulfate displaces clonidine at α2-adrenergic and at imidazoline receptors and was recently shown to exert some neuroprotective effects. It blocks NMDA-receptor associated cation channels. Acts as a competitive inhibitor of nitric oxide synthase (NOS). It functions as neurotransmitter since it is stored in synaptic vesicles and is related from axon terminals by depolarization(1). Protects autistic behavior in rats and reverses depressive like behavior in mice.

Description

Agmatine sulfate is the sulfate of the Agmatine. Agmatine is an aninoguanidine that is naturally derived from the arginine. It can exert modulatory effect on many molecular targets such as neurotransmitter systems, opioid analgesia, ion channels, and nitric oxide (NO) synthesis and polyamine metabolism. It has been also found that it can reverse the pain induced from inflammation, neuropathy, and spinal cord injury. Those effects make it a potential candidate for multiple pharmacological applications in the future.

Chemical Properties

White to off-white powder

Uses

Different sources of media describe the Uses of 2482-00-0 differently. You can refer to the following data:
1. Agmatine Sulfate is a a polyamine derived from L-arginine (A769500) decarboxylation and is a known putative endogenous neurotransmitter at imidazoline receptors. Agmatine sulfate displaces clonidine a t α2-adrenergic and at imidazoline receptors and was recently shown to exert some neuroprotective effects.
2. Agmatine is an intermediate in the biosynthesis of the polyamines putrescine and spermine. Agmatine binds with high affinity to α2-adrenergic receptors and imidazoline binding sites and produces blockade of the NMDA-receptor associated cation channels. Agmatine is a competitive inhibitor of nitric oxide synthase activity owing to mimicry of the natural NOS substrate arginine.

Biological Activity

Arginine metabolite that is synthesized within bovine brain and exhibits clonidine-displacing substance (CDS) activity. Putative endogenous ligand for the imidazoline binding site.

Biochem/physiol Actions

Putative endogenous neurotransmitter at imidazoline receptors; displaces clonidine at α2-adrenergic and at imidazoline receptors; blocks NMDA-activated ion channels in hippocampal neurons.

Purification Methods

Crystallise the salt from aqueous MeOH. The free base has m 101.5-103o, the gold chloride hydrochloride crystallises from H2O with m 223o(dec), and the picrate has m 236-238o. [Odo J Chem Soc Jpn 67 132 1946, Beilstein 4 I 420, 4 II 703, 4 III 575, 4 IV 1291.]

References

Fairbanks, C. A., et al. "Agmatine reverses pain induced by inflammation, neuropathy, and spinal cord injury." Proceedings of the National Academy of Sciences of the United States of America97.19(2000):10584. Kolesnikov, Yuri, S. Jain, and G. W. Pasternak. "Modulation of opioid analgesia by agmatine." European Journal of Pharmacology296.1(1996):17-22. Su, R. B., J. Li, and B. Y. Qin. "A biphasic opioid function modulator: agmatine. "Acta Pharmacologica Sinica24.7(2003):631. Galea, Elena, et al. "Inhibition of mammalian nitric oxide synthases by agmatine, an endogenous polyamine formed by decarboxylation of arginine." Biochemical Journal 316 ( Pt 1).1(1996):247. https://en.wikipedia.org/wiki/Agmatine

Check Digit Verification of cas no

The CAS Registry Mumber 2482-00-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,4,8 and 2 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 2482-00:
(6*2)+(5*4)+(4*8)+(3*2)+(2*0)+(1*0)=70
70 % 10 = 0
So 2482-00-0 is a valid CAS Registry Number.
InChI:InChI=1/C5H14N4.H2O4S/c6-3-1-2-4-9-5(7)8;1-5(2,3)4/h1-4,6H2,(H4,7,8,9);(H2,1,2,3,4)

2482-00-0 Well-known Company Product Price

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  • Alfa Aesar

  • (H55363)  Agmatine sulfate, 97%   

  • 2482-00-0

  • 250mg

  • 530.0CNY

  • Detail
  • Alfa Aesar

  • (H55363)  Agmatine sulfate, 97%   

  • 2482-00-0

  • 1g

  • 773.0CNY

  • Detail
  • Alfa Aesar

  • (H55363)  Agmatine sulfate, 97%   

  • 2482-00-0

  • 5g

  • 2343.0CNY

  • Detail
  • Aldrich

  • (101443)  Agmatine sulfate salt  Enzymatic decarboxylation product of arginine., 97%

  • 2482-00-0

  • 101443-5G

  • 2,439.45CNY

  • Detail

2482-00-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-(4-aminobutyl)guanidine,sulfuric acid

1.2 Other means of identification

Product number -
Other names Prestwick_710

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:2482-00-0 SDS

2482-00-0Synthetic route

2-methylisothiourea sulphate
14527-26-5, 867-44-7

2-methylisothiourea sulphate

1,4-diaminobutane
110-60-1

1,4-diaminobutane

agmatine sulphate
2482-00-0

agmatine sulphate

1,4-diaminobutane
110-60-1

1,4-diaminobutane

S-ethyl-isothiourea sulfate

S-ethyl-isothiourea sulfate

agmatine sulphate
2482-00-0

agmatine sulphate

agmatine sulphate
2482-00-0

agmatine sulphate

acryloyl chloride
814-68-6

acryloyl chloride

N-(4-guanidino-butyl)acrylamide
181147-64-8

N-(4-guanidino-butyl)acrylamide

Conditions
ConditionsYield
Stage #1: agmatine sulphate With potassium carbonate In water at 0 - 5℃; for 0.166667h;
Stage #2: acryloyl chloride In water; acetone at 5℃; for 1h;
Stage #3: With sulfuric acid; potassium carbonate Product distribution / selectivity; more than 3 stages;
95%
Stage #1: agmatine sulphate With sodium hydroxide In water at 0℃; pH=12;
Stage #2: acryloyl chloride With sodium hydroxide In water; acetone at 0 - 20℃; for 2h; pH=11.8;
Stage #3: With sulfuric acid In water; acetone pH=2.5; Product distribution / selectivity;
50%
Stage #1: agmatine sulphate With potassium carbonate In water at 5℃; for 0.166667h; Cooling with ice;
Stage #2: acryloyl chloride In water; acetone at 5℃; for 1h;
With sodium hydrogencarbonate In water at 0℃; for 1.5h;1 g
Stage #1: agmatine sulphate; acryloyl chloride With sodium hydrogencarbonate at 0℃; for 1h;
Stage #2: With hydrogenchloride In water pH=1;
1 g
N-succinimidyl-3-(p-hydroxyphenyl)propionate
34071-95-9

N-succinimidyl-3-(p-hydroxyphenyl)propionate

agmatine sulphate
2482-00-0

agmatine sulphate

3-(4-hydroxyphenyl)propionyl agmatine

3-(4-hydroxyphenyl)propionyl agmatine

Conditions
ConditionsYield
With sodium hydrogencarbonate In acetone for 19h; pH=8;91%
2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzofurane-1,3(2H,9bH)-dione

2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzofurane-1,3(2H,9bH)-dione

agmatine sulphate
2482-00-0

agmatine sulphate

C23H28N4O6

C23H28N4O6

Conditions
ConditionsYield
With triethylamine In ethanol; water at 20℃; for 20h; Inert atmosphere; Reflux;82%
agmatine sulphate
2482-00-0

agmatine sulphate

4-O-metyl-cis-p-coumaryl succinimide ester
672341-25-2

4-O-metyl-cis-p-coumaryl succinimide ester

cis-p-methoxycinnamoylagmatine

cis-p-methoxycinnamoylagmatine

Conditions
ConditionsYield
With sodium hydrogencarbonate In acetone for 72h; pH=8.0;81%
cetyl chloroformate
26272-90-2

cetyl chloroformate

agmatine sulphate
2482-00-0

agmatine sulphate

hexadecyl N-(4-guanidinobutyl)carbamate hydrochloride

hexadecyl N-(4-guanidinobutyl)carbamate hydrochloride

Conditions
ConditionsYield
Stage #1: agmatine sulphate With sodium hydroxide In water; isopropyl alcohol at 10 - 20℃; pH=12 - 13;
Stage #2: cetyl chloroformate With hydrogenchloride In ethyl acetate at 20℃; for 0.5h;
72%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

agmatine sulphate
2482-00-0

agmatine sulphate

4-(tert-Butoxycarbonylamino)butylguanidinium hydrogen carbonate

4-(tert-Butoxycarbonylamino)butylguanidinium hydrogen carbonate

Conditions
ConditionsYield
With sodium hydrogencarbonate In 1,4-dioxane68%
With sodium hydrogencarbonate In 1,4-dioxane at 20℃;68%
agmatine sulphate
2482-00-0

agmatine sulphate

4-hydroxycinnamic acid N-hydroxysuccinimide ester
88492-43-7

4-hydroxycinnamic acid N-hydroxysuccinimide ester

1-(trans-4'-hydroxycinnamoylamino)-4-guanidinobutane

1-(trans-4'-hydroxycinnamoylamino)-4-guanidinobutane

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone for 24h; Ambient temperature; pH: 8;65%
agmatine sulphate
2482-00-0

agmatine sulphate

(S)-2-Benzyloxycarbonylamino-5-tert-butoxycarbonylamino-pentanoic acid 2,5-dioxo-pyrrolidin-1-yl ester
116115-11-8

(S)-2-Benzyloxycarbonylamino-5-tert-butoxycarbonylamino-pentanoic acid 2,5-dioxo-pyrrolidin-1-yl ester

Z-Orn(Boc)-Agm*0.5H2SO4

Z-Orn(Boc)-Agm*0.5H2SO4

Conditions
ConditionsYield
With triethylamine In water; acetonitrile51%
hexadecyl isocyanate
1943-84-6

hexadecyl isocyanate

agmatine sulphate
2482-00-0

agmatine sulphate

1-(4-guanidinobutyl)-3-hexadecyl-urea hydrochloride

1-(4-guanidinobutyl)-3-hexadecyl-urea hydrochloride

Conditions
ConditionsYield
Stage #1: hexadecyl isocyanate; agmatine sulphate With sodium hydroxide In water; isopropyl alcohol at 30℃; pH=13;
Stage #2: With hydrogenchloride In water; ethyl acetate at 20℃; for 2h;
38%
agmatine sulphate
2482-00-0

agmatine sulphate

cis-p-coumaroylsuccinimide
672341-24-1

cis-p-coumaroylsuccinimide

cis-p-coumaroylagmatine

cis-p-coumaroylagmatine

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone Ambient temperature;5.7%
N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

agmatine sulphate
2482-00-0

agmatine sulphate

4-phthalimidobutylguanidine sulfate

4-phthalimidobutylguanidine sulfate

Conditions
ConditionsYield
With sodium hydrogencarbonate In water for 1h; Ambient temperature;225 mg
agmatine sulphate
2482-00-0

agmatine sulphate

γ-guanidino butyraldehyde
14049-14-0

γ-guanidino butyraldehyde

Conditions
ConditionsYield
diamine oxidase and beef liver catalase In various solvent(s) at 36℃;
agmatine sulphate
2482-00-0

agmatine sulphate

putrescine dihydrochloride
333-93-7

putrescine dihydrochloride

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide 1) water, ethanol, reflux, cca. 20 h; 2) r.t.; Yield given. Multistep reaction;
agmatine sulphate
2482-00-0

agmatine sulphate

4-hydroxycinnamic acid N-hydroxysuccinimide ester
88492-43-7

4-hydroxycinnamic acid N-hydroxysuccinimide ester

acetic acid
64-19-7

acetic acid

trans-p-coumaroylagmatine acetate

trans-p-coumaroylagmatine acetate

Conditions
ConditionsYield
With sodium hydrogencarbonate 1.) H2O, Me2CO, RT, 24 h; Yield given. Multistep reaction;
agmatine sulphate
2482-00-0

agmatine sulphate

(3S)-3-methyldecanoic acid N-hydroxysuccinimide ester

(3S)-3-methyldecanoic acid N-hydroxysuccinimide ester

aplysillamide B

aplysillamide B

Conditions
ConditionsYield
With sodium hydrogencarbonate In tetrahydrofuran; water for 44h; Ambient temperature; Yield given;
agmatine sulphate
2482-00-0

agmatine sulphate

4-hydroxycinnamic acid N-hydroxysuccinimide ester
88492-43-7

4-hydroxycinnamic acid N-hydroxysuccinimide ester

trans-p-coumaroylagmatine

trans-p-coumaroylagmatine

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone Ambient temperature;
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid

agmatine sulphate
2482-00-0

agmatine sulphate

trans-feruloylagmatine

trans-feruloylagmatine

Conditions
ConditionsYield
Stage #1: (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid With thionyl chloride for 0.5h; Substitution; Heating;
Stage #2: agmatine sulphate In N,N-dimethyl-formamide at 20℃; for 12h; Condensation;
agmatine sulphate
2482-00-0

agmatine sulphate

(2'E,4'E,6'S)-3-(4''-Guanidinobutyl)-1-(2',6',10'-trimethylundeca-2',4',9'-trienoyl)guanidine

(2'E,4'E,6'S)-3-(4''-Guanidinobutyl)-1-(2',6',10'-trimethylundeca-2',4',9'-trienoyl)guanidine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 68 percent / aq. NaHCO3 / dioxane
2.1: TMSCl; iPr2NEt / CH2Cl2
2.2: 62 percent / iPr2NEt / CH2Cl2
3.1: 84 percent / p-TsOH; 2-methyl-2-butene / methanol
4.1: methanol
5.1: KOH; MeOH
View Scheme
Multi-step reaction with 5 steps
1.1: 68 percent / aq. NaHCO3 / dioxane / 20 °C
2.1: DIPEA; TMSCl / CH2Cl2 / 1 h / 40 °C
2.2: 197 mg / DIPEA / CH2Cl2 / 4 h / 40 °C
3.1: 84 percent / p-TsOH / methanol; various solvent(s) / 20 °C
4.1: 75 percent / Et3N / methanol / 1 h / 20 °C
5.1: KOH / methanol / 4 h / 10 °C
View Scheme
agmatine sulphate
2482-00-0

agmatine sulphate

(2'E,4'E,6'R)-3-(4''-Guanidinobutyl)-1-(2',6',10'-trimethylundeca-2',4',9'-trienoyl)guanidine

(2'E,4'E,6'R)-3-(4''-Guanidinobutyl)-1-(2',6',10'-trimethylundeca-2',4',9'-trienoyl)guanidine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 68 percent / aq. NaHCO3 / dioxane
2.1: TMSCl; iPr2NEt / CH2Cl2
2.2: iPr2NEt / CH2Cl2
3.1: p-TsOH; 2-methyl-2-butene / methanol
4.1: methanol
5.1: KOH; MeOH
View Scheme
Multi-step reaction with 5 steps
1.1: 68 percent / aq. NaHCO3 / dioxane / 20 °C
2.1: DIPEA; TMSCl / CH2Cl2 / 1 h / 40 °C
2.2: 202 mg / DIPEA / CH2Cl2 / 4 h / 40 °C
3.1: 81 percent / p-TsOH / methanol; various solvent(s) / 20 °C
4.1: 83 percent / Et3N / methanol / 1 h / 20 °C
5.1: KOH / methanol / 4 h / 10 °C
View Scheme
agmatine sulphate
2482-00-0

agmatine sulphate

N-(4-amino-butyl)-N',N''-bis-(2,6,10-trimethyl-undeca-2,4,9-trienoyl)-guanidine
345238-71-3

N-(4-amino-butyl)-N',N''-bis-(2,6,10-trimethyl-undeca-2,4,9-trienoyl)-guanidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 68 percent / aq. NaHCO3 / dioxane
2.1: TMSCl; iPr2NEt / CH2Cl2
2.2: iPr2NEt / CH2Cl2
3.1: p-TsOH; 2-methyl-2-butene / methanol
View Scheme
agmatine sulphate
2482-00-0

agmatine sulphate

N-(4-amino-butyl)-N',N''-bis-(2,6,10-trimethyl-undeca-2,4,9-trienoyl)-guanidine
345238-66-6

N-(4-amino-butyl)-N',N''-bis-(2,6,10-trimethyl-undeca-2,4,9-trienoyl)-guanidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 68 percent / aq. NaHCO3 / dioxane
2.1: TMSCl; iPr2NEt / CH2Cl2
2.2: 62 percent / iPr2NEt / CH2Cl2
3.1: 84 percent / p-TsOH; 2-methyl-2-butene / methanol
View Scheme
agmatine sulphate
2482-00-0

agmatine sulphate

{4-[N',N''-bis-(2,6,10-trimethyl-undeca-2,4,9-trienoyl)-guanidino]-butyl}-carbamic acid tert-butyl ester
345238-70-2

{4-[N',N''-bis-(2,6,10-trimethyl-undeca-2,4,9-trienoyl)-guanidino]-butyl}-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 68 percent / aq. NaHCO3 / dioxane
2.1: TMSCl; iPr2NEt / CH2Cl2
2.2: iPr2NEt / CH2Cl2
View Scheme
agmatine sulphate
2482-00-0

agmatine sulphate

{4-[N',N''-bis-(2,6,10-trimethyl-undeca-2,4,9-trienoyl)-guanidino]-butyl}-carbamic acid tert-butyl ester
345238-62-2

{4-[N',N''-bis-(2,6,10-trimethyl-undeca-2,4,9-trienoyl)-guanidino]-butyl}-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 68 percent / aq. NaHCO3 / dioxane
2.1: TMSCl; iPr2NEt / CH2Cl2
2.2: 62 percent / iPr2NEt / CH2Cl2
View Scheme
agmatine sulphate
2482-00-0

agmatine sulphate

N-{4-[N',N''-bis-(2,6,10-trimethyl-undeca-2,4,9-trienoyl)-guanidino]-butyl}-guanidine; compound with sulfurous acid

N-{4-[N',N''-bis-(2,6,10-trimethyl-undeca-2,4,9-trienoyl)-guanidino]-butyl}-guanidine; compound with sulfurous acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 68 percent / aq. NaHCO3 / dioxane
2.1: TMSCl; iPr2NEt / CH2Cl2
2.2: iPr2NEt / CH2Cl2
3.1: p-TsOH; 2-methyl-2-butene / methanol
4.1: methanol
View Scheme
agmatine sulphate
2482-00-0

agmatine sulphate

N-{4-[N',N''-bis-(2,6,10-trimethyl-undeca-2,4,9-trienoyl)-guanidino]-butyl}-guanidine; compound with sulfurous acid

N-{4-[N',N''-bis-(2,6,10-trimethyl-undeca-2,4,9-trienoyl)-guanidino]-butyl}-guanidine; compound with sulfurous acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 68 percent / aq. NaHCO3 / dioxane
2.1: TMSCl; iPr2NEt / CH2Cl2
2.2: 62 percent / iPr2NEt / CH2Cl2
3.1: 84 percent / p-TsOH; 2-methyl-2-butene / methanol
4.1: methanol
View Scheme
agmatine sulphate
2482-00-0

agmatine sulphate

(2'E,4'E,6'R)-3-(4''-Aminobutyl)-1,2-bis(2',6',10'-trimethylundeca-2',4',9'-trienoyl)guanidine
345238-71-3

(2'E,4'E,6'R)-3-(4''-Aminobutyl)-1,2-bis(2',6',10'-trimethylundeca-2',4',9'-trienoyl)guanidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 68 percent / aq. NaHCO3 / dioxane / 20 °C
2.1: DIPEA; TMSCl / CH2Cl2 / 1 h / 40 °C
2.2: 202 mg / DIPEA / CH2Cl2 / 4 h / 40 °C
3.1: 81 percent / p-TsOH / methanol; various solvent(s) / 20 °C
View Scheme
agmatine sulphate
2482-00-0

agmatine sulphate

(2'E,4'E,6'S)-3-(4''-Aminobutyl)-1,2-bis(2',6',10'-trimethylundeca-2',4',9'-trienoyl)guanidine
345238-66-6

(2'E,4'E,6'S)-3-(4''-Aminobutyl)-1,2-bis(2',6',10'-trimethylundeca-2',4',9'-trienoyl)guanidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 68 percent / aq. NaHCO3 / dioxane / 20 °C
2.1: DIPEA; TMSCl / CH2Cl2 / 1 h / 40 °C
2.2: 197 mg / DIPEA / CH2Cl2 / 4 h / 40 °C
3.1: 84 percent / p-TsOH / methanol; various solvent(s) / 20 °C
View Scheme

2482-00-0Relevant articles and documents

PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS

-

, (2010/03/02)

The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.

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