Synthesis of creatine (kreatin; N-methyl-N-guanylglycine)

Preparation of creatine

Preparation of creatine from raw meat

500 g of meat, separated from fat, are put through a sausage machine or finely chopped and digested with half a liter of water at 50-60° C, and well stirred from time to time. It is filtered through cloth, and is then digested with a further 250 ml of water in the same way filtered, and the cloth removed from the frame and squeezed into the filtrate. The filtrate is heated to boiling to coagulate the protein, and, on cooling, filtered. Basic acetate of lead (prepared by boiling a solution of lead acetate with excess of lead oxide and filtering when cold) is carefully added, just sufficient to precipitate the soluble protein. The liquid is again filtered through a fluted filler and the lead removed with hydrogen sulfide, which is passed into the warm liquid. The filtrate from the lead sulfide is concentrated, and then transferred to a vacuum desiccator, dried over sulfuric acid. In a short time, more quickly on the addition of a crystal of creatine, crystalline needles begin to separate, and, when no further crystallization is observed, the crystals, which have a brown color, are brought on to a porcelain funnel and washed with a little spirit. They are recrystallized from a little hot water with the addition of activated charcoal. The yield is about 1 gram.

A Class-Book of Organic Chemistry, by J. B. Cohen, 55-56, 1919

IUPAC Name

2-[carbamimidoyl(methyl)amino]acetic acid

InChI

InChI=1S/C4H9N3O2/c1-7(4(5)6)2-3(8)9/h2H2,1H3,(H3,5,6)(H,8,9)

InChI Key

CVSVTCORWBXHQV-UHFFFAOYSA-N

Canonical SMILES

CN(CC(=O)O)C(=N)N

MeSH Synonyms

Creatine

Depositor-Supplied Synonyms

creatine, Creatin, Kreatin, Krebiozon, N-methyl-N-guanylglycine, N-amidinosarcosine, 57-00-1, (alpha-Methylguanido)acetic acid, Creatine, hydrate, Pyrolysate, Glycine, N-(aminoiminomethyl)-N-methyl-, methylglycocyamine, 2-(1-Methylguanidino)acetic acid, Creatine (8CI), Methylguanidoacetic acid, Phosphagen, Creatine anhydrous, Cosmocair C 100, N-carbamimidoyl-N-methylglycine, alpha-Methylguanidino acetic acid, UNII-MU72812GK0, CHEBI:16919, NSC8752, CVSVTCORWBXHQV-UHFFFAOYSA-N, (.alpha.-Methylguanido)acetic acid, NSC 8752, (N-methylcarbamimidamido)acetic acid, N-(aminoiminomethyl)-N-methylglycine, N-(Aminoiminomethyl)-N-methyl-glycine, 2-(1-methylcarbamimidamido)acetic acid, 2-[carbamimidoyl(methyl)amino]acetic acid, AI3-15320, ((amino(imino)methyl)(methyl)amino)acetic acid, N-[(E)-AMINO(IMINO)METHYL]-N-METHYLGLYCINE, 2-(amidinomethylamino)acetic acid, ((amino(imino)methyl)(methyl)amino)acetate, [[Amino(imino)methyl](methyl)amino]acetate, [[Amino(imino)methyl](methyl)amino]acetic acid, Methylguanidoacetate, bmse000078, bmse000950, bmse000999, AC1Q3X9W, AC1Q3X9X, (alpha-Methylguanido)acetate, ACMC-1AN76, SCHEMBL21567, KSC489M9H, C0780_SIGMA, Creatine, hydrate (Salt/Mix), 291196_ALDRICH, AC1L19K7, CHEMBL283800, GTPL4496, 2-(Methylguanidino)ethanoic acid, CTK3I9693, HMDB00064, HSDB 7336, MolPort-001-785-682, BB_NC-2326, MU72812GK0, NSC-8752, EINECS 200-306-6, BBL012187, SBB028240, STL163516, AKOS005717096, DB00148, MCULE-3625061513, N-[amino(imino)methyl]-N-methylglycine, RTR-019943, AJ-46230, AK113717, AN-23572, KB-49125, H6237, ST24027430, ST51010435, 2302-EP2295061A1, 2302-EP2298783A1, 2302-EP2301536A1, 2302-EP2301538A1, 2302-EP2311455A1, 2302-EP2316452A1, C00300, [[Amino(imino)methyl](methyl)amino]acetic acid #, I14-7700, 3B3-033099

Removed Synonyms

Creatine hydrate, Unknown Ligand, Creatine monohydrate, CID586, c0396, (DIAMINOMETHYL-METHYL-AMINO)-ACETIC ACID, D003401, CRN, 6020-87-7, IOM, UNL

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