Glycocyamine

Glycocyamine
Names



Other names 2-Guanidinoacetic acid
Identifiers
CAS Number	352-97-6^Y
3DMet	B00139
Beilstein Reference	1759179
ChEBI	CHEBI:16344^N
ChEMBL	ChEMBL281593^N
ChemSpider	743^N
DrugBank	DB02751^N
EC Number	206-529-5
Jmol interactive 3D	Image Image
KEGG	C00581^N
MeSH	glycocyamine
PubChem	763
UNII	GO52O1A04E^Y
InChI InChI=1S/C3H7N3O2/c4-3(5)6-1-2(7)8/h1H2,(H,7,8)(H4,4,5,6)^N Key: BPMFZUMJYQTVII-UHFFFAOYSA-N^N
SMILES [nH]:c(:[nH2]):[nH]Cc(:[o]):[oH] NC(=N)NCC(O)=O
Properties
Chemical formula	C₃H₇N₃O₂
Molar mass	117.11 g·mol⁻¹
Appearance	White crystals
Odor	Odourless
Melting point	300 °C (572 °F; 573 K)
log P	−1.11
Acidity (pK_a)	3.414
Basicity (pK_b)	10.583
Hazards
GHS pictograms
GHS signal word	WARNING
GHS hazard statements	H315, H319, H335
GHS precautionary statements	P261, P305+351+338
EU classification (DSD)	Xi
R-phrases	R36/37/38
S-phrases	S26, S36
Related compounds
Related alkanoic acids	Sarcosine Dimethylglycine Creatine N-Methyl-D-aspartic acid beta-Methylamino-L-alanine Guanidinopropionic acid
Related compounds	Dimethylacetamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

Glycocyamine (or guanidinoacetate) is a metabolite of glycine in which the amino group has been converted into a guanidine.

Glycocyamine is a direct precursor of creatine and is used as a supplement. However the metabolism of creatine from glycocyamine in the liver causes a depletion of methyl groups. This causes homocysteine levels to rise, which has been shown to produce cardiovascular and skeletal problems.

Uses

A series of studies showed that a combination of betaine and glycocyamine improves the symptoms of patients with chronic illness, including heart disease, without toxicity. Betaine can provide a methyl group to glycocyamine, via methionine, for the formation of creatine. ^[1] In overall, such treatment led to less fatigue, greater strength and endurance, and an improved sense of well-being. The patients with cardiac decompensation (arteriosclerosis or rheumatic disease) ^[2] and congestive heart failure ^[3] had improved cardiac function. The patients gained weight (improved nitrogen balance) and saw lessened symptoms of arthritis and asthma and increased libido, and those people suffering from hypertension experienced transient reduced blood pressure. Also the studies shows the increase of glucose tolerance in both diabetic subjects and subjects without diabetes. ^[4]

References

↑ Borsook H, Borsook ME. The biochemical basis of betaine-glycocyamine therapy. Ann West Med Surg 1951;5:825–9.
↑ Borsook ME, Borsook H. Treatment of cardiac decompensation with betaine and glycocyamine. Ann West Med Surg 1951;5:830–55.
↑ Van Zandt V, Borsook H. New biochemical approach to the treatment of congestive heart failure. Ann West Med Surg 1951;5:856–62.
↑ Stuart AS Craig (September 2004). "Betaine in human nutrition". American Journal of Clinical Nutrition 80 (3): 539–549. PMID 15321791. Retrieved 2010-02-10.

lysine→	Saccharopine Allysine α-Aminoadipic acid α-Ketoadipate Glutaryl-CoA Glutaconyl-CoA Crotonyl-CoA β-Hydroxybutyryl-CoA

leucine→	α-Ketoisocaproic acid Isovaleryl-CoA 3-Methylcrotonyl-CoA 3-Methylglutaconyl-CoA HMG-CoA

tryptophan→alanine→	N'-Formylkynurenine Kynurenine Anthranilic acid 3-Hydroxykynurenine 3-Hydroxyanthranilic acid 2-Amino-3-carboxymuconic semialdehyde 2-Aminomuconic semialdehyde 2-Aminomuconic acid Glutaryl-CoA

G→pyruvate→citrate

glycine→serine→	3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine

G→glutamate→
α-ketoglutarate

histidine→	Urocanic acid Imidazol-4-one-5-propionic acid Formiminoglutamic acid Glutamate-1-semialdehyde

proline→	1-Pyrroline-5-carboxylic acid

arginine→	Agmatine Ornithine Cadaverine Putrescine

other	cysteine+glutamate→glutathione: γ-Glutamylcysteine

G→propionyl-CoA→
succinyl-CoA

valine→	α-Ketoisovaleric acid Isobutyryl-CoA Methacrylyl-CoA 3-Hydroxyisobutyryl-CoA 3-Hydroxyisobutyric acid 2-Methyl-3-oxopropanoic acid

isoleucine→	2,3-Dihydroxy-3-methylpentanoic acid 2-Methylbutyryl-CoA Tiglyl-CoA 2-Methylacetoacetyl-CoA

methionine→	generation of homocysteine: S-Adenosyl methionine S-Adenosyl-L-homocysteine Homocysteine conversion to cysteine: Cystathionine alpha-Ketobutyric acid+Cysteine

threonine→	α-Ketobutyric acid

propionyl-CoA→	Methylmalonyl-CoA

G→fumarate

phenylalanine→tyrosine→	4-Hydroxyphenylpyruvic acid Homogentisic acid 4-Maleylacetoacetic acid

G→oxaloacetate

see urea cycle

Other

Cysteine metabolism	Cysteine sulfinic acid

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Glycocyamine

Uses

References

See also