Trimethylglycine

Trimethylglycine
Names
	IUPAC name (Trimethylammonio)acetate
	Other names Betaine; TMG; glycine betaine; N,N,N-trimethylglycine; Cystadane; Amversio;
Identifiers
CAS Number	107-43-7 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	3537113
ChEBI	CHEBI:17750 ;
ChEMBL	ChEMBL1182 ;
ChemSpider	242 ;
DrugBank	DB06756 ;
ECHA InfoCard	100.003.174
EC Number	203-490-6;
Gmelin Reference	26434
IUPHAR/BPS	4550;
KEGG	C00719;
MeSH	Betaine
PubChem CID	247;
UNII	3SCV180C9W ;
CompTox Dashboard (EPA)	DTXSID8022666 ;
	InChI InChI=1S/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3 Key: KWIUHFFTVRNATP-UHFFFAOYSA-N ; 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) (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; US: ℞-only; EU: Rx-only;
Hazards
	GHS labelling:
Pictograms
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). verify (what is ?) Infobox references

Trimethylglycine is an amino acid derivative with the formula (CH₃)₃N⁺CH₂CO−2. A colorless, water-soluble solid, it occurs in plants.^[5] Trimethylglycine is a zwitterion: the molecule contains both a quaternary ammonium group and a carboxylate group. Trimethylglycine was the first betaine discovered; originally it was simply called betaine because it was discovered in sugar beets (Beta vulgaris subsp. vulgaris).^[6] Several other betaines are now known.

^ "Notice of Amendment: Betaine removed from the Prescription Drug List (PDL)". Health Canada. 6 January 2023. Retrieved 3 January 2024.
^ "Cystadane- betaine powder, for solution". DailyMed. 3 October 2019. Archived from the original on 4 August 2021. Retrieved 29 July 2022.
^ "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.
^ "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.
^ Ashraf M, Foolad M (2007). "Roles of glycine betaine and proline in improving plant abiotic stress resistance". Environmental and Experimental Botany. 59 (2): 206–216. Bibcode:2007EnvEB..59..206A. doi:10.1016/j.envexpbot.2005.12.006.
^ Schiweck H, Clarke M, Pollach G. "Sugar". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a25_345.pub2. ISBN 978-3-527-30673-2.

[1] "Notice of Amendment: Betaine removed from the Prescription Drug List (PDL)". Health Canada. 6 January 2023. Retrieved 3 January 2024.

[Cystadane_FDA_label-2] "Cystadane- betaine powder, for solution". DailyMed. 3 October 2019. Archived from the original on 4 August 2021. Retrieved 29 July 2022.

[Cystadane_EPAR-3] "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.

[Amversio_EPAR-4] "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.

[Ashraf-5] Ashraf M, Foolad M (2007). "Roles of glycine betaine and proline in improving plant abiotic stress resistance". Environmental and Experimental Botany. 59 (2): 206–216. Bibcode:2007EnvEB..59..206A. doi:10.1016/j.envexpbot.2005.12.006.

[Ullmann-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 978-3-527-30673-2.

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