35404-50-3

Usage

Uses

Used in Pharmaceutical Industry:
CYCLOCREATINE is used as a regulatory agent for creatine biosynthesis, specifically by suppressing the level of arginine:glycine amidinotransferase in chick liver. This application is essential for maintaining the balance of creatine production in the body, which is vital for various physiological processes and energy metabolism.
Used in Research and Development:
CYCLOCREATINE is also utilized in research and development for studying the mechanisms of creatine biosynthesis and its role in cellular energy production. This knowledge can be applied to develop new therapeutic strategies and interventions for conditions related to energy metabolism and muscle function.

InChI:InChI=1/C5H9N3O2/c6-5-7-1-2-8(5)3-4(9)10/h1-3H2,(H2,6,7)(H,9,10)

Synthetic route

CYANAMID (420-04-2) + N-(2-Aminoethyl)glycine (24123-14-6) → 1-carboxymethyl-2-iminoimidazolidine (35404-50-3)

Conditions	Yield
In water at 70℃; for 27.5h; Temperature;	58%

1-carboxymethyl-3-benzyl-2-iminoimidazolidine (63784-10-1) → 1-carboxymethyl-2-iminoimidazolidine (35404-50-3)

Conditions	Yield
With sodium In water Product distribution / selectivity;

1-carboxymethyl-2-iminoimidazolidine (35404-50-3) → dilithium 1-carboxymethyl-3-phosphono-2-iminoimidazolidine

Conditions	Yield
Stage #1: 1-carboxymethyl-2-iminoimidazolidine With lithium hydroxide; trichlorophosphate for 2h; Heating / reflux; Stage #2: With hydrogenchloride In water Product distribution / selectivity;
Stage #1: 1-carboxymethyl-2-iminoimidazolidine With lithium hydroxide; water; trichlorophosphate In water at -20 - 0℃; for 2h; Stage #2: With hydrogenchloride In water pH=7.2; Product distribution / selectivity;

maleic acid (110-16-7) + 1-carboxymethyl-2-iminoimidazolidine (35404-50-3) → cyclocreatine maleate

Conditions	Yield
In ethanol; water for 0.0833333h;

oxalic acid (144-62-7) + 1-carboxymethyl-2-iminoimidazolidine (35404-50-3) → cyclocreatine oxalate

Conditions	Yield
In ethanol; water for 0.0833333h;

benzenesulfonic acid (98-11-3) + 1-carboxymethyl-2-iminoimidazolidine (35404-50-3) → cyclocreatine benzenesulfonate

Conditions	Yield
In dichloromethane; water for 0.166667h;

Upstream product

• 420-04-2 CYANAMID 
• 24123-14-6 N-(2-Aminoethyl)glycine 
• 63784-10-1 1-carboxymethyl-3-benzyl-2-iminoimidazolidine 

Relevant academic research and scientific papers

SYNTHESIS OF CYCLOCREATINE AND ANALOGS THEREOF

Provided herein is a process and intermediates for the preparation of a compound of formula (I): or a pharmaceutically acceptable salt thereof, using cyanamide in the reaction.

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

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.

Methods and compositions for diagnosing and treating arthritic disorders and regulating bone mass

The present invention relates to improved diagnostic methods for early detection of a risk for developing an arthritic disorder in humans, and screening assays for therapeutic agents useful in the treatment of arthritic disorders, by comparing the levels of one or more indicators of altered mitochondrial function. Indicators of altered mitochondrial function include enzymes such as mitochondrial enzymes and ATP biosynthesis factors. Other indicators of altered mitochondrial function include mitochondrial mass, mitochondrial number and mitochondrial DNA content, cellular responses to elevated intracellular calcium and to apoptogens, and free radical production. Methods of treating, and of stratifying, human patients as such methods relate to disclosed indicators of altered mitchondrial function are also provided.

PHOSPHAGEN SYNTHESIS

Cyclocreatine phosphate can be prepared in large quantities from inexpensive starting materials to afford a stable product.