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Trimethylglycine information


Trimethylglycine
Names
IUPAC name
(Trimethylammonio)acetate
Other names
  • Betaine
  • TMG
  • glycine betaine
  • N,N,N-trimethylglycine
  • Cystadane
  • Amversio
Identifiers
CAS Number
  • 107-43-7 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
3537113
ChEBI
  • CHEBI:17750 ☒N
ChEMBL
  • ChEMBL1182 checkY
ChemSpider
  • 242 checkY
DrugBank
  • DB06756 ☒N
ECHA InfoCard 100.003.174 Edit this at Wikidata
EC Number
  • 203-490-6
Gmelin Reference
26434
IUPHAR/BPS
  • 4550
KEGG
  • C00719
MeSH Betaine
PubChem CID
  • 247
UNII
  • 3SCV180C9W checkY
CompTox Dashboard (EPA)
  • DTXSID8022666 Edit this at Wikidata
InChI
  • InChI=1S/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3 checkY
    Key: KWIUHFFTVRNATP-UHFFFAOYSA-N checkY
  • InChI=1/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3
    Key: KWIUHFFTVRNATP-UHFFFAOYAI
SMILES
  • C[N+](C)(C)CC(=O)[O-]
Properties
Chemical formula
C5H11NO2
Molar mass 117.146
Appearance White solid
Melting point 180 °C (356 °F; 453 K)[1] (decomposes)
Solubility in water
Soluble
Solubility Methanol
Acidity (pKa) 1.84
Pharmacology
ATC code
A16AA06 (WHO)
License data
  • EU EMA: by Betaine anhydrous
Routes of
administration
By mouth
Legal status
  • CA: OTC[2]
  • US: ℞-only[3]
  • EU: Rx-only[4][5]
Hazards
GHS labelling:
Pictograms
GHS07: Exclamation mark
Signal word
Warning
Hazard statements
H315, H319
Precautionary statements
P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362
Related compounds
Related amino acids
Glycine
Methylglycine
Dimethylglycine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Trimethylglycine is an amino acid derivative that occurs in plants. Trimethylglycine was the first betaine discovered; originally it was simply called betaine because, in the 19th century, it was discovered in sugar beets (Beta vulgaris subsp. vulgaris).[6]

  1. ^ Acheson RM, Bond GJ (1956). "52. Addition reactions of heterocyclic compounds. Part II. Phenanthridine and methyl acetylenedicarboxylate in methanol". J. Chem. Soc. 1956: 246. doi:10.1039/JR9560000246.
  2. ^ "Notice of Amendment: Betaine removed from the Prescription Drug List (PDL)". Health Canada. 6 January 2023. Retrieved 3 January 2024.
  3. ^ "Cystadane- betaine powder, for solution". DailyMed. 3 October 2019. Archived from the original on 4 August 2021. Retrieved 29 July 2022.
  4. ^ "Cystadane EPAR". European Medicines Agency. 17 September 2018. Archived from the original on 1 July 2022. Retrieved 29 July 2022. Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
  5. ^ "Amversio EPAR". European Medicines Agency. 21 February 2022. Archived from the original on 30 July 2022. Retrieved 29 July 2022. Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
  6. ^ Schiweck H, Clarke M, Pollach G. "Sugar". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a25_345.pub2. ISBN 978-3527306732.

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Trimethylglycine

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Trimethylglycine is an amino acid derivative that occurs in plants. Trimethylglycine was the first betaine discovered; originally it was simply called...

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Choline

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donor in metabolic one-carbon chemistry. The compound is related to trimethylglycine in the latter respect. It is a cation with the chemical formula [(CH3)3NCH2CH2OH]+...

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Betaine

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adjacent to the cationic site. Historically, the term was reserved for trimethylglycine (TMG), which is involved in methylation reactions and detoxification...

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Zwitterion

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This allows experimental analysis of the equilibrium. The compound trimethylglycine, which was isolated from sugar beet, was named as "betaine". Later...

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Sarcosine

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glycine. Sarcosine, like the related compounds dimethylglycine (DMG) and trimethylglycine (betaine, TMG), is formed via the metabolism of nutrients such as choline...

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Betaine reductase

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thioredoxin disulfide ⇌ {\displaystyle \rightleftharpoons } N,N,N-trimethylglycine + phosphate + thioredoxin The 3 substrates of this enzyme are acetyl...

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Glycine

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determination). With methyl iodide, the amine becomes quaternized to give trimethylglycine, a natural product: H 3N+ CH 2COO− + 3 CH3I → (CH 3) 3N+ CH 2COO− +...

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Lipotropic

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Betaine itself (in a non-hydrochloric form, also known as TMG or Trimethylglycine) also has a lipotropic effect. Quinoa is high in betaine.[citation...

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Dimethylglycine

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found in beans and liver, and has a sweet taste. It can be formed from trimethylglycine upon the loss of one of its methyl groups. It is also a byproduct of...

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Homocystinuria

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(especially monitoring methionine), and most will need treatment with trimethylglycine. A normal dose of folic acid supplement and occasionally adding cysteine...

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Methionine

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Homocysteine can also be remethylated using glycine betaine (N,N,N-trimethylglycine, TMG) to methionine via the enzyme betaine-homocysteine methyltransferase...

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TMG

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for detecting muscle properties Tetramethylguanidine, a superbase Trimethylglycine, an amino acid derivative Trimethylgallium, Ga(CH3)3 Touring motor...

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C5H11NO2

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3-Methyl-GABA N-Methylmorpholine N-oxide Norvaline Pentyl nitrite Trimethylglycine Valine This set index page lists chemical structure articles associated...

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Hyperhomocysteinemia

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homocysteine back to methionine also exists, involving methylation with trimethylglycine (also called betaine or abbreviated to TMG) as a methyl donor. The...

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Chloral betaine

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Mead Johnson in the United States in 1963. It is a betaine complex of trimethylglycine with chloral hydrate, which acts as an extended-acting formulation...

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Arsenobetaine

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main source of arsenic found in fish. It is the arsenic analog of trimethylglycine, commonly known as betaine. The biochemistry and its biosynthesis are...

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Osmotic shock

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Myo-Inositol Taurine and Taurine-transporting ATPase Creatine Betaines Trimethylglycine – A Betaine and metabolite of Choline Sorbitol Glycerophosphocholine...

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Trimethyl ammonium compounds

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its derivatives Choline and its derivatives Methacholine Muscarine Trimethylglycine Benzyltrimethylammonium Trimethyl+ammonium+compounds at the U.S. National...

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Autism therapies

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peer-reviewed studies have addressed treatment with the related compound trimethylglycine. Melatonin is sometimes used to manage sleep problems. Adverse effects...

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Remethylation

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involves betaine-homocysteine methyltransferase (BHMT) and requires trimethylglycine as a cofactor. Remethylation also has a role in epigenetics and neuroplasticity...

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Colin Raston

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comparatively low toxicity. Arsenobetaine is an analog of betaine (trimethylglycine) and with similar biosynthesis to choline and betaines. He later received...

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