Edit filter log

'{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 419118341 |ImageFile=Betain2.svg |ImageSize= |ImageFile1=Betaine-from-xtal-1999-3D-balls.png |IUPACName=2-trimethylammonioacetate |OtherNames= {{unbulleted list|Betaine|TMG|glycine betaine|''N'',''N'',''N''-trimethylglycine}} |Section1= {{Chembox Identifiers | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 3SCV180C9W | InChI = 1/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3 | InChIKey = KWIUHFFTVRNATP-UHFFFAOYAI | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 1182 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = KWIUHFFTVRNATP-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo=107-43-7 | PubChem=247 | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 17750 | SMILES=C[N+](C)(C)CC(=O)[O-] | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 242 | MeSHName=Betaine | ATCCode_prefix = A16 | ATCCode_suffix = AA06 }} |Section2= {{Chembox Properties | Formula=C₅H₁₁NO₂ | MolarMass=117.146 | Appearance=White solid | Density= | Melting_ref = <ref>{{cite journal|last1=Acheson|first1=R. M.|last2=Bond|first2=G. J. F.|title=52. Addition reactions of heterocyclic compounds. Part II. Phenanthridine and methyl acetylenedicarboxylate in methanol|journal=Journal of the Chemical Society (Resumed)|pages=246|doi=10.1039/JR9560000246}}</ref> | Melting_notes = (decomposes) | MeltingPtC = 180 | BoilingPt= | Solubility= Soluble | SolubleOther = Methanol }} |Section3= {{Chembox Hazards | MainHazards= | FlashPt= | Autoignition= }} |Section8= {{Chembox Related | OtherFunctn= [[Glycine]]<br>[[Sarcosine|Methylglycine]]<br>[[Dimethylglycine]] | Function= [[amino acid]]s }} }} '''Trimethylglycine''' ('''TMG''') is an [[organic compound]] 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 beet]]s.<ref name=Ullmann>Hubert Schiweck, Margaret Clarke, Günter Pollach "Sugar” in Ullmann’s Encyclopedia of Industrial Chemistry 2007, Wiley-VCH, Weinheim.{{DOI|10.1002/14356007.a25_345.pub2}}</ref> Since then, many other betaines have been discovered, and the more specific name ''glycine betaine'' distinguishes this one. == Structure and reactions == Trimethylglycine is an N-trimethylated amino acid. This [[quaternary ammonium cation|quaternary ammonium]] exists as the [[zwitterion]] at neutral pH. Strong acids such as [[hydrochloric acid]] convert TMG to various salts, with [[Hydrochloric acid|HCl]] yielding betaine hydrochloride: :(CH₃)₃N⁺CH₂CO₂^- + HCl → [(CH₃)₃N⁺CH₂CO₂H]Cl^- [[Demethylation]] of TMG gives [[dimethylglycine]]. Degradation of TMG yields [[trimethylamine]], the scent of putrifying fish. ==Production and biochemical processes== [[Food processing|Processing]] [[sucrose]] from sugar beets yields glycine betaine as a [[byproduct]]. The value of the TMG rivals that of the sugar content in sugar beets.<ref name=Makela/> Glycine betaine production involves [[chromatography|chromatographic separation]]. === Biosynthesis === In most organisms, glycine betaine is biosynthesized by oxidation of [[choline]] in two steps. The intermediate, [[betaine aldehyde]], is generated by the action of the enzyme mitochondrial choline oxidase ([[choline dehydrogenase]], EC 1.1.99.1). Betaine aldehyde is further oxidised in the [[mitochondria]] or cytoplasm to betaine by the enzyme called betaine aldehyde dehydrogenase (EC 1.1.1.8).<ref name=Kempf>Kempf, B.; Bremer, E."Uptake and synthesis of compatible solutes as microbial stress responses to high-osmolality environments" Arch Microbiol. 1998, volume 170, pp. 319-30. {{DOI|10.1074/jbc.M210970200}}<!--PMID 981835--></ref> === Biological function === TMG is an organic [[osmolyte]] that occurs in high concentrations (10s of millimolar) in many marine invertebrates, such as crustaceans and molluscs. It serves as a potent appetitive attractant to generalist carnivores such as the predatory sea-slug ''Pleurobranchaea californica''.<ref>{{cite journal | pmid = 10737805 | volume=97 | issue=7 | title=Cost-benefit analysis potential in feeding behavior of a predatory snail by integration of hunger, taste, and pain | pmc=16283 |date=March 2000 | journal=Proc. Natl. Acad. Sci. U.S.A. | pages=3585–90 | author=Gillette R, Huang RC, Hatcher N, Moroz LL | doi=10.1073/pnas.97.7.3585}}</ref> TMG is an important [[Cofactor (biochemistry)|cofactor]] in [[methylation]], a process that occurs in every cell of mammals to synthesize and donate [[methyl group]]s (CH₃) for other processes in the body. These processes include the synthesis of [[neurotransmitter]]s such as [[dopamine]], [[serotonin]]. Methylation is also required for the biosynthesis of [[melatonin]] and the [[electron transport chain]] constituent [[coenzyme Q10]]. The major step in the methylation cycle is the remethylation of homocysteine, which can occur via either of two pathways. The major pathway involves the enzyme [[methionine synthase]], which requires vitamin B₁₂ as a cofactor, and also depends indirectly on [[folate]] and various other B vitamins. The minor pathway involves [[betaine-homocysteine methyltransferase]] and requires TMG as a cofactor. Betaine is thus involved in the synthesis of many biologically important molecules, and may be even more important in situations where the major pathway for the regeneration of methionine from homocysteine has been compromised by genetic polymorphisms. ==TMG in agriculture and aquaculture== [[Factory farming|Factory farms]] supplement [[fodder]] with TMG and [[lysine]] to increase livestocks' [[muscle mass]] (and, therefore, "carcass yield", the amount of usable meat). [[Salmon farm]]s apply TMG to relieve the osmotic pressure on salmons' cells when workers transfer the fish from freshwater to saltwater.<ref name="Makela">P. Mäkelä "Agro-industrial uses of glycinebetaine" Sugar Tech 2004 Volume 6, 207-212. {{DOI|10.1007/BF02942500}}</ref><ref name="Xue">Xue, M. Xie, S. & Cui Y. (2004). Effect of a feeding stimulant on feeding adaptation of gibel carp ''Carassius auratus gibelio'' (Bloch), fed diets with replacement of fish meal by meat and bone meal. Aquaculture Research, 35: 473-482.</ref> TMG supplementation decreases the amount of [[adipose tissue]] in pigs; however, research in human subjects has shown no effect on body weight, body composition, or resting energy expenditure.<ref name="pmid12399266">{{cite journal |author=Schwab U, Törrönen A, Toppinen L, et al. |title=Betaine supplementation decreases plasma homocysteine concentrations but does not affect body weight, body composition, or resting energy expenditure in human subjects |journal=Am. J. Clin. Nutr. |volume=76 |issue=5 |pages=961–7 |date=November 2002 |pmid=12399266 |doi= |url=http://www.ajcn.org/cgi/pmidlookup?view=long&pmid=12399266}}</ref> == TMG in the human diet == {| class="wikitable" |+ TMG in foods |- ! Food ! TMG per 100g |- | [[Quinoa]] | 630&nbsp;mg |- | [[Spinach]] | 577&nbsp;mg |- | [[Wheat]] [[bran]] | 360&nbsp;mg |- | [[Lamb's quarters]] | 332&nbsp;mg |- | [[Beet]] | 256&nbsp;mg |} === Nutritional supplement === Although TMG supplementation decreases the amount of [[adipose tissue]] in pigs, research on human subjects has shown no effect on body weight, body composition, or resting energy expenditure when used in conjunction with a hypoenergetic diet.<ref name="pmid12399266"/> The Food and Drug Administration of the United States approved '''anhydrous trimethylglycine''' (also known by the brand name '''Cystadane''') for the treatment of [[homocystinuria]], a disease caused by abnormally high [[homocysteine]] levels at birth.<ref name="homocysteine">{{cite journal | pmid = 15550695 | doi=10.1161/01.ATV.0000151283.33976.e6 | volume=25 | issue=2 | title=Betaine and folate status as cooperative determinants of plasma homocysteine in humans |date=February 2005 | journal=Arterioscler. Thromb. Vasc. Biol. | pages=379–85 | author=Holm PI, Ueland PM, Vollset SE, et al.}}</ref> TMG supplementation may cause [[diarrhea]], stomach upset, or [[nausea]]. Obese persons or those with kidney disease supplementing with TMG, [[folic acid]], and [[vitamin B6]] can experience an increase in total cholesterol levels.<ref>http://www.umm.edu/altmed/articles/betaine-000287.htm</ref> === Other uses: PCR ===<!--seems highly specialized--> Trimethylglycine can act as an [[adjuvant]] of the [[polymerase chain reaction]] (PCR) process, and other [[DNA polymerase]]-based assays such as [[DNA sequencing]]. By an unknown mechanism, it aids in the prevention of secondary structures in the DNA molecules, and prevents problems associated with the amplification and sequencing of GC-rich regions. Trimethylglycine makes [[guanosine]] and [[cytidine]] (strong binders) behave with thermodynamics similar to those of [[thymidine]] and [[adenosine]] (weak binders). It has been determined under experiment that it is best used at a final concentration of 1M.<ref name="pmid9380524">{{cite journal |author=Henke W, Herdel K, Jung K, Schnorr D, Loening SA |title=Betaine improves the PCR amplification of GC-rich DNA sequences. |journal=Nucleic Acids Res |volume=25 |issue=19 |pages=3957–8 |date=October 1997 |pmid=9380524 |doi= 10.1093/nar/25.19.3957|url=http://www.pubmed.com/9380524 |pmc=146979}}</ref> === Speculative uses ===<!--for lack of a better term--> Laboratory studies and two clinical trials have indicated that TMG is a potential treatment of non-alcoholic [[steatohepatitis]].<ref>{{cite journal | author = Angulo P, Lindor KD | title = Treatment of nonalcoholic fatty liver: present and emerging therapies | journal =Semin Liver Dis | volume =21 | issue =1 | pages =81–88 | year =2001 | doi = 10.1055/s-2001-12931 | pmid = 11296699}}</ref><ref>{{cite journal |author=Abdelmalek MF, Sanderson SO, Angulo P, et al. |title=Betaine for nonalcoholic fatty liver disease: results of a randomized placebo-controlled trial |journal=Hepatology |volume=50 |issue=6 |pages=1818–26 |date=December 2009 |pmid=19824078 |doi=10.1002/hep.23239 |url=}}</ref><ref>{{cite journal |author=Miglio F, Rovati LC, Santoro A, Setnikar I |title=Efficacy and safety of oral betaine glucuronate in non-alcoholic steatohepatitis. A double-blind, randomized, parallel-group, placebo-controlled prospective clinical study |journal=Arzneimittelforschung |volume=50 |issue=8 |pages=722–7 |date=August 2000 |pmid=10994156 |doi= 10.1055/s-0031-1300279|url=}}</ref> TMG is sometimes used as a treatment for depression, as it can increase [[S-adenosylmethionine]] (SAMe) by remethylating homocysteine. SAMe has been shown to work as a nonspecific antidepressant in several studies.<ref> {{cite web | title = Investigating SAM-e | publisher = Geriatric Times | year = 2001 | url = http://www.geriatrictimes.com/g010923.html | accessdate = 2006-12-08 }} </ref><ref> {{cite journal | title = Oral S-adenosylmethionine in depression: a randomized, double-blind, placebo-controlled trial | last=Kagan | first=BL |author2=Sultzer, DL |author3=Rosenlicht, N |author4= Gerner, RH | journal = Am J Psychiatry | date = May 1, 1990 | volume = 147 | pages = 591–5 | pmid = 2183633 | url = http://www.ajp.psychiatryonline.org/cgi/content/abstract/147/5/591 | accessdate = 2007-02-16 | issue = 5 }} </ref><ref> {{cite journal | title = The antidepressant potential of oral S-adenosyl-l-methionine | last=Rosenbaum | first=JF |author2=Fava, M |author3=Falk, WE |author4=Pollack, MH |author5=Cohen, LS |author6=Cohen, BM |author7= Zubenko, GS | journal = [[Acta Psychiatrica Scandinavica]] |date=May 1990 | volume = 81 | issue = 5 | pages = 432–6 | pmid = 2113347 | doi = 10.1111/j.1600-0447.1990.tb05476.x }} </ref> === IEX Ion Exchange Chromatography === In the book from Amersham Biosciences/GE Healthcare, Ion Exchange Chromatography & Chromatofocusing - Principles and Methods, page48. "Zwitterionic additives such as betaine can prevent precipitation and can be used at high concentrations without interfering with the gradient elution" == References == {{Reflist|2}} == External links == * [http://www.ars.usda.gov/SP2UserFiles/Place/12354500/Data/Choline/Choln02.pdf USDA Database for the Choline Content of Common Foods] - including the data on choline metabolites, such as betaine, in 434 food items. * [http://nootropicfish.com/trimethylglycne/ Article] at [[Trimethylglycine -Nootropic Fish]] {{Neurotransmitters}} {{Glycinergics}} [[Category:Amino acids]] [[Category:Quaternary ammonium compounds]] [[Category:Zwitterions]]'