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Agmatine sulfate

(4-aminobutyl)guanidinium sulphate

CAS: 2482-00-0

Molecular Formula: C5H16N4O4S

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Agmatine sulfate - Names and Identifiers

Name (4-aminobutyl)guanidinium sulphate
Synonyms Agmatine sulfate
4-GUANIDINOBUTANE SULFATE
2-(4-aminobutyl)guanidine
4-GUANIDINO-BUTYLAMINE SULFATE
1-AMINO-4-GUANIDOBUTANE SULFATE
(4-Aminobutyl)guanidine sulphate
(4-Aminobutyl)guanidinium sulfate
2-(4-aminobutyl)guanidine sulfate
N-(4-AMINOBUTYL)GUANIDINE SULFATE
1-AMINO-4-GUANIDINOBUTANE SULFATE
(4-aminobutyl)guanidinium sulphate
4-GUANIDINO-BUTYLAMINE SULFATE SALT
1-AMINO-4-GUANIDINOBUTANE SULFATE SALT
N-(4-Aminobutyl)guanidine sulfate salt
CAS 2482-00-0
EINECS 219-617-3
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)
InChIKey PTAYFGHRDOMJGC-UHFFFAOYSA-N

Agmatine sulfate - Physico-chemical Properties

Molecular FormulaC5H16N4O4S
Molar Mass228.27
Melting Point234-238°C(lit.)
Boling Point281.4°C at 760 mmHg
Flash Point124°C
Water SolubilitySoluble in water, nearly insoluble in alcohol
Solubility H2O: 50mg/mL
Vapor Presure0.00357mmHg at 25°C
AppearanceWhite to white-like powder
Colorwhite to off-white
Merck14,188
BRN3918807
Storage ConditionKeep in dark place,Inert atmosphere,Room temperature
MDLMFCD00013109

Agmatine sulfate - Risk and Safety

Safety DescriptionS22 - Do not breathe dust.
S24/25 - Avoid contact with skin and eyes.
WGK Germany3
RTECSME8413000
FLUKA BRAND F CODES10
HS Code29252900

Agmatine sulfate - Reference

Reference
Show more
1. Wang Bingxin, Hao Xiaoqing, Wang Cailing, Wu Ning, Li Jin. Effects of agmatine on spatial reference memory in mice under physiological and stress conditions [J]. International Journal of Pharmaceutical Research, 2020,47(09):722-730 737.
2. Zhang Shaohua, Zhang Yanfang, Cao Meng, Li Yan, Liao Lixia, Wang Beibei. Agmatine attenuates propofol-induced neurotoxicity in neonatal rats by modulating Nrf2/HO-1 signaling pathway [J]. Chinese Journal of Comparative Medicine, 2020,30(12):17-22 119.

Agmatine sulfate - Reference Information

background and overview agmatine is a product of arginine decarboxylation catalyzed by L-arginine decarboxylase (L-ADC). It is a neurotransmitter distributed in most organs and tissues of mammals, and its content is organ-specific, such as adrenal chromaffin cells, glial cells and carotid body globular cells. Research data show that agmatine has biological activities such as lowering blood sugar, lowering blood pressure, diuresis, anti-inflammatory, antidepressant, and inhibiting cell proliferation, especially for N-methyl-D-aspartate receptors. The antagonistic effect is strong and long-lasting, and has a abstinence effect on animal morphine. It is a drug detoxification drug with great development value. As a medicinal salt of agmatine, the market application prospect of agmatine sulfate is broad. And agmatine works by stimulating the release of hormones in the hypothalamus, including luteinizing hormone and growth hormone, and increases the content of nitric oxide in two ways: stimulating the release of nitric oxide and inhibiting the synthesis of nitric oxide enzymes, It can improve the body's tolerance, accelerate the body's recovery (generally refers to the recovery after exercise), improve body performance, show amazing and long-term energy transportation, and improve the body composition.
synthetic route route 1: using 1, 4-butyldiamine as raw material, first protect it with monoamine group, and then use 1-nitroguanidinyl -3, 5-dimethylpyrazole to nitroguanidine group of another amine group, and then reduce, deprotect, and salt to finally prepare guanidinylbutylamine sulfate, see the figure for details:

Route 2: First, diethyl adipate is reacted with hydrazine hydrate to prepare adipate dihydrazide, and then it is reacted with sodium nitrite to obtain diazonium salt, heat denitrification to generate 1, 4-diisocyanate butane, hydrolysis to obtain the key intermediate 1, 4-butyldiamine, and then react with S-methyl isothiourea sulfate to prepare guanidyl butylamine sulfate. The specific reaction process is as follows:


route 3: using 1, 4-dibromobutane and potassium phthalamide as raw materials, the three-step reaction of substitution, amination and guanidine is used to obtain guanidine sulfate, the synthesis route has short reaction steps, and the clean guanidine reagent O-methyl isothiourea sulfate is replaced by S-methyl isothiourea sulfate, it has the advantages of simple operation, low cost, low energy consumption, and less emission of three wastes. The specific reaction process is as follows:



Route 4: 1, 4-butyldiamine is used as raw material, and S-methyl isothiourea sulfate is used as guanidine reagent, as shown in the following reaction formula:

Route 5: 1, 4-butyldiamine is used as raw material, using an aqueous solution of cyanamide as a guanidine-based reagent, agmatine is obtained through an addition reaction, and then sulfuric acid is used to form a salt to obtain:

Route 6: A synthesis method of agmatine sulfate, including the following steps: In the reaction solvent, 1,4-butylamine and O-methylisourea sulfate undergo a condensation reaction under the conditions of -20~100°C, TLC detects the reaction to the end point, the reaction solution is filtered, the alcohol solution of sulfuric acid is added dropwise to the obtained filtrate, the pH value of the filtrate is adjusted below 7.0, concentrated to dry, and the residue is recrystallized to obtain agmatine sulfate; The reaction solvent is water or C1-C3 alcohol; The molar ratio of 1, 4-butylene diamine to O-methylisourea sulfate is 1:1~1:2.0; the volume dosage of the reaction solvent is 4-20ml/g based on the mass of O-methylisourea sulfate. The invention has simple and safe operation, high reaction yield, low production cost, basically no "three wastes" discharge, and has great implementation value and social and economic benefits. The specific reaction process is as follows:

Route 7: A biotransformation method of agmatine sulfate, comprising: using L-arginine as a substrate and arginine decarboxylase as a biotransformation catalyst, performing decarboxylation reaction to generate a crude agmatine product, and acidifying the crude agmatine product with dilute sulfuric acid to obtain a crude agmatine sulfate product. The method is simple in process, has no special requirements for equipment, and is suitable for industrial production. Compared with the simple chemical method, the method has mild reaction conditions, simple operation, low cost, less pollution, and can complete the enzyme catalytic reaction that is difficult to carry out in chemical reactions.
application agmatine has biological activities such as lowering blood sugar, lowering blood pressure, diuresis, anti-inflammatory, antidepressant, inhibiting cell proliferation, etc., especially for N-methyl-D-aspartic acid The receptor has a strong and long-lasting antagonistic effect, has a abstinence effect on animal morphine, and is a drug with great development value.
Main references [1] Yan Jianxiang et al. Synthesis method of agmatine sulfate. Application No. CN201410032661.2. Application Date 2014-01-23.
[2] Chen Jianhua. A biotransformation method of agamidine sulfate. Application No.: 201610181488.1 Application Date: 2016-03-28
[3] Ye Shanshan et al. Study on Green Synthesis Process of agamidine sulfate. Zhejiang chemical industry. 2010,41(9):5-7.
[4] Dan Wei Guang et al. A synthesis method of agmatine sulfate. Application No. CN200910154924.6. Application Date 2009-11-30.
biological activity Agmatine sulfate is an active metabolite of arginine, which can increase nitric oxide level, reduce blood sugar level and increase growth hormone level.
TargetValue
Last Update：2024-04-09 19:05:11
Agmatine sulfate
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Agmatine sulfate
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