Glycocyamine

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Glycocyamine
Other names

2-Guanidinoacetic acid[citation needed]

Identifiers
CAS number 352-97-6 YesY
PubChem 763
ChemSpider 743 YesY
UNII GO52O1A04E YesY
EC number 206-529-5
DrugBank DB02751
KEGG C00581 YesY
MeSH glycocyamine
ChEBI CHEBI:16344 YesY
ChEMBL CHEMBL281593 YesY
Beilstein Reference 1759179
3DMet B00139
Jmol-3D images {{#if:[nH]:c(:[nH2]):[nH]Cc(:[o]):[oH]NC(=N)NCC(O)=O|Image 1
Image 2
Properties
Molecular 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 (pKa) 3.414
Basicity (pKb) 10.583
Hazards
GHS pictograms
GHS signal word WARNING
GHS hazard statements H315, H319, H335
GHS precautionary statements P261, P305+351+338
EU classification Xi
R-phrases R36/37/38
S-phrases S26, S36
Related compounds
Related alkanoic acids
Related compounds Dimethylacetamide
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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 overal, 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

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

See also

K→acetyl-CoA
G
G→pyruvate→citrate
G→glutamate→
α-ketoglutarate
other
G→fumarate
G→oxaloacetate
Other

M: MET

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m (A16/C10), i (k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)

  • Biochemical families: carbohydrates
    • alcohols
    • glycoproteins
    • glycosides
  • lipids
    • eicosanoids
    • fatty acids / intermediates
    • phospholipids
    • sphingolipids
    • steroids
  • nucleic acids
    • constituents / intermediates
  • proteins
    • Amino acids / intermediates
  • tetrapyrroles / intermediates
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