BETAINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C5H11NO2
Molecular Weight	117.1465
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[N+](C)(C)CC(=O)[O-]

InChI

InChIKey=KWIUHFFTVRNATP-UHFFFAOYSA-N

InChI=1S/C5H11NO2/c1-6(2,3)4-5(7)8/h4H2,1-3H3

HIDE SMILES / InChI

Molecular Formula	C5H11NO2
Molecular Weight	117.1465
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15321791 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020576s010lbl.pdf

Betaine is a methyl derivative of glycine first isolated from the juice of sugar beets. Betaine is found in many common foods, but concentrated significantly in beets, spinach, wheat foods, and shellfish. In addition, betaine can be synthesized within the human body. Betaine participates in the methionine cycle, which produces vital biomolecules including proteins, hormones, phospholipids, polyamines, and nutrients. Betaine is used as a dietary supplement and has a beneficial effect on the human health. In the USA, FDA approved a betaine-containing drug Cystadane for the treatment of homocystinuria. The drug acts as a methyl group donor in the remethylation of homocysteine to methionine.

CNS Activity

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Homocystinuria 4 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020576s010lbl.pdf	Primary		Approved 8043	CYSTADANE Approved Use Cystadane is a methylating agent indicated for the treatment of homocystinuria to decrease elevated homocysteine blood levels. Included within the category of homocystinuria are Cystathionine beta-synthase (CBS) deficiency, 5,10-methylenetetrahydrofolate reductase (MTHFR) deficiency, Cobalamin cofactor metabolism (cbl) defect. Launch Date 8.4620162E11

C_max

Value	Dose	Co-administered	Analyte	Population
1.456 mM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12534635	50 mg/kg bw 2 times / day multiple, oral dose: 50 mg/kg bw route of administration: Oral experiment type: MULTIPLE co-administered:		BETAINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
0.939 mM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12534635	50 mg/kg bw single, oral dose: 50 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:		BETAINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
12.528 mM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12534635	50 mg/kg bw 2 times / day multiple, oral dose: 50 mg/kg bw route of administration: Oral experiment type: MULTIPLE co-administered:		BETAINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
5.518 mM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12534635	50 mg/kg bw single, oral dose: 50 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:		BETAINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
41.17 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12534635	50 mg/kg bw 2 times / day multiple, oral dose: 50 mg/kg bw route of administration: Oral experiment type: MULTIPLE co-administered:		BETAINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
14.38 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12534635	50 mg/kg bw single, oral dose: 50 mg/kg bw route of administration: Oral experiment type: SINGLE co-administered:		BETAINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
20 g 1 times / day multiple, oral Highest studied dose Dose: 20 g, 1 times / day Route: oral Route: multiple Dose: 20 g, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020576s014lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020576s014lbl.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/020576s014lbl.pdf

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY34236	https://www.001chemical.com/chem/107-43-7
3B Scientific (Wuhan) Corp	3B1-00584	http://www.3bsc.com/index/pro_info.php?id=20796
AA Blocks	AA00HATM	http://www.aablocks.com/goods/Goods/detail?id=AA00HATM
AHH Chemical co.,ltd	NP-0873	http://www.ahhchemical.com/product/NP-0873.html
AK Scientific, Inc. (AKSCI)	71671	http://www.aksci.com/item_detail.php?cat=71671
Aaron Chemicals	AR00HBLE	http://www.aaronchem.com/107-43-7
Accela ChemBio Inc	SY011295	http://www.accelachem.com/cn/search.html?keyword=SY011295&attname=GoodsCode
Achemo Scientific Limited	AC-14975	http://www.achemo.com/product_view.asp?ID=4865
Achemtek	0104-004453	http://www.achemtek.com/107-43-7
Acorn PharmaTech	ACN-035633	http://www.acornpharmatech.com/
Acros Organics	AC204240050	https://www.fishersci.com/shop/products/betaine-98-analysis-anhydrous-acros-organics-1/AC204240050
Acros Organics	AC204241000	https://www.fishersci.com/shop/products/betaine-98-analysis-anhydrous-acros-organics-1/AC204241000
Acros Organics	AC204240025	https://www.fishersci.com/shop/products/betaine-98-analysis-anhydrous-acros-organics-3/AC204240025
Acros Organics	AC204245000	https://www.fishersci.com/shop/products/betaine-98-analysis-anhydrous-acros-organics/AC204245000
Alfa Aesar	B24397	https://www.alfa.com/en/catalog/B24397/
Alfa Chemistry	AP107437	https://reagents.alfa-chemistry.com/product/betaine-cas-107-43-7-1340.html
Angene	AGN-PC-0OX8FI	http://www.angenechemical.com/productshow/AGN-PC-0OX8FI.html
ApexBio Technology	N1709	http://www.apexbt.com/betaine-14407.html
Ark Pharm	AK161874	http://www.arkpharminc.com/products/107-43-7.html
Ark Pharma Scientific Limited	N-1215	http://www.arkpharmtech.com/product/241556.html
Aurora Fine Chemicals LLC	K02.096.342	http://online.aurorafinechemicals.com/info?ID=K02.096.342
Avantor Inc	BT144585-100G	https://us.vwr.com/store/product/16637042/betaine-anhydrous-98
Avantor Inc	200011-386	https://us.vwr.com/store/product/18600427/betaine-anhydrous-98-for-analysis
Avantor Inc	700007-544	https://us.vwr.com/store/product/9581405/betaine-anhydrous
Avantor Inc	700007-546	https://us.vwr.com/store/product/9581405/betaine-anhydrous
Avantor Inc	700007-550	https://us.vwr.com/store/product/9581405/betaine-anhydrous
BLD Pharm	BD41085	http://www.bldpharm.com/products/107-43-7.html
BenchChem	B521028	https://www.benchchem.com/product/b521028
BioChemPartner	BCP21888	http://www.biochempartner.com/107-43-7-BCP21888
BioCrick	BCN6303	http://www.biocrick.com/Betaine-BCN6303.html
BioSynth	Q-200708	https://www.biosynth.com/en/products/chemical-intermediates/basic-intermediates/products/Q-200708.html
Boerchem	BC653158	http://www.boerchem.com/?product_38944.html
CSNpharm	CSN16679	https://www.csnpharm.com/products/betaine.html
Chem Scene	CS-2947	http://www.chemscene.com/107-43-7.html
ChemFaces	CFN99546	http://www.chemfaces.com/natural/Betaine-CFN99546.html
ChemMol	44013286	http://www.chemmol.com/chemmol/44013286.html
ChemMol	49414342	http://www.chemmol.com/chemmol/49414342.html
ChemMol	49415265	http://www.chemmol.com/chemmol/49415265.html
Chemspace	CSSB00000033712	https://chem-space.com/CSSB00000033712
Clearsynth	CS-T-49071	https://www.clearsynth.com/en/CST49071.html
DC Chemicals	DCT-010	http://www.dcchemicals.com//product_show-Betaine.html
Enamine	Z2756787719	https://www.enaminestore.com/catalog/Z2756787719
Finetech	FT-0622917	http://www.finetechnology-ind.com/prod/detail/pub/107-43-7.html
Glentham Life Sciences	GE1604	http://www.glentham.com/products/product/GE1604/
Hairui	HR130963	http://www.hairuichem.com/en/product/107-43-7.html
Herbest Bio-Tech	HH231683	http://www.bjherbest.com/analytical-standard/alkaloids/betaine-107-43-7.html
LGC Standards	DRE-C10574900	https://www.lgcstandards.com/US/en/p/DRE-C10574900
LGC Standards	MM3894.00-1000	https://www.lgcstandards.com/US/en/p/MM3894.00-1000
Lab Network	LN00194831	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00194831
MedChem Express	HY-B0710	http://www.medchemexpress.com/betaine.html
Molcore	MC34236	https://www.molcore.com/product/107-43-7
MuseChem	I000342	https://www.musechem.com/product/I000342.html
Parchem	18343	http://www.parchem.com/chemical-supplier-distributor/Caprylic-Amidopropyl-Betaine-008343.aspx
Parchem	5509	http://www.parchem.com/chemical-supplier-distributor/Trimethylglycine-007278.aspx
Parchem	19622	http://www.parchem.com/chemical-supplier-distributor/betaine-009622.aspx
Shanghai Send Pharmaceutical Technology Co., Ltd	send36394	http://shsendpharm.com/
Smolecule	S521028	http://www.smolecule.com/products/s521028
TCI (Tokyo Chemical Industry)	B0455	http://www.tcichemicals.com/eshop/en/us/commodity/B0455/index.html
THE BioTek	bt-261765	https://www.thebiotek.com/product/inhibitors/bt-261765
VladaChem	VL140518	https://www.vladachem.com/product.php?products=107-43-7
VladaChem	VL267574-100G	https://www.vladachem.com/product.php?products=107-43-7
Yuhao Chemical	HL1358	http://www.chemyuhao.com/107-43-7.html
abcr GmbH	AB131717	http://www.abcr.com/shop/en/AB131717
iChemical	EBD2156815	http://www.ichemical.com/products/107-43-7.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-8745470661	https://mcule.com/MCULE-8745470661/

PubMed

Title	Date	PubMed
Isolation of glycine betaine and proline betaine from human urine. Assessment of their role as osmoprotective agents for bacteria and the kidney.	1987 Mar	3546377
Strychnine-dependent allodynia in the urethane-anesthetized rat is segmentally distributed and prevented by intrathecal glycine and betaine.	1995 Dec	8834483
Simple method for the routine determination of betaine and N,N-dimethylglycine in blood and urine.	1998 Sep	9732980
Betaine and homocysteine concentrations in infant formulae and breast milk.	2001 Dec	11737741
An open-label, 24-week pilot study of the methyl donor betaine in Alzheimer disease patients.	2001 Jul-Sep	11522934
Betaine, a promising new agent for patients with nonalcoholic steatohepatitis: results of a pilot study.	2001 Sep	11569700
Mechanism of the inhibitory effect of zwitterionic drugs (levofloxacin and grepafloxacin) on carnitine transporter (OCTN2) in Caco-2 cells.	2006 Nov	16928358
Consideration of betaine and one-carbon sources of N5-methyltetrahydrofolate for use in homocystinuria and neural tube defects.	2007 Apr	17413090
Betaine-homocysteine S-methyltransferase-2 is an S-methylmethionine-homocysteine methyltransferase.	2008 Apr 4	18230605
Long follow up of betaine therapy in two Japanese siblings with cystathionine beta-synthase deficiency.	2008 Oct	19261122
Assessment of the effect of betaine on p16 and c-myc DNA methylation and mRNA expression in a chemical induced rat liver cancer model.	2009 Jul 30	19642983
Identification of a novel organic anion transporter mediating carnitine transport in mouse liver and kidney.	2010	20332632
Effects of betaine on lipopolysaccharide-induced memory impairment in mice and the involvement of GABA transporter 2.	2011 Nov 4	22053950
Dietary supplementation with methyl donors reduces fatty liver and modifies the fatty acid synthase DNA methylation profile in rats fed an obesogenic diet.	2013 Jan	22648174
Alterations in hepatic metabolism of sulfur amino acids in non-obese type-2 diabetic Goto-Kakizaki rats.	2013 Jul 5	23665415
Survival and psychomotor development with early betaine treatment in patients with severe methylenetetrahydrofolate reductase deficiency.	2014 Feb	24323041
Betaine supplementation protects against renal injury induced by cadmium intoxication in rats: role of oxidative stress and caspase-3.	2014 Mar	24632105
Betanin reduces the accumulation and cross-links of collagen in high-fructose-fed rat heart through inhibiting non-enzymatic glycation.	2015 Feb 5	25559852
Regulation of signal transducer and activator of transcription 3 and apoptotic pathways by betaine attenuates isoproterenol-induced acute myocardial injury in rats.	2015 May	25080425

Patents

Sample Use Guides

In Vivo Use Guide

The usual dosage in adult and pediatric patients is 6 grams per day administered orally in divided doses of 3 grams twice daily. In pediatric patients less than 3 years of age, dosage may be started at 100 mg/kg/day divided in twice daily doses, and then increased weekly by 50 mg/kg increments.

Route of Administration: Oral

In Vitro Use Guide

HeLa cells were treated with 0.1, 1.0, 5.0, 20.0, 100.0 mg/ml of betaine to evaluate the anticancer efficacy of the compound. The percentage of S phase cells in the low dose groups (< 5mg/ml) were distinctly higher than in high dose groups, and the rates of Sub-G1 phase were the opposite. A high concentration of betaine (>5.0mg/ml) significantly promoted the apoptosis of HeLa cells.

Substance Class	Chemical Created by `admin` on `Sat Jun 26 09:17:44 UTC 2021` Edited by `admin` on `Sat Jun 26 09:17:44 UTC 2021`
Record UNII	3SCV180C9W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BETAINE

Official Name

English

BETAINE [ORANGE BOOK]

Common Name

English

BETAINE [MI]

Common Name

English

(TRIMETHYLAMMONIO)ACETATE

Systematic Name

English

METHANAMINIUM, 1-CARBOXY-N,N,N-TRIMETHYL-

Systematic Name

English

BETAINE [FCC]

Common Name

English

BETAINE [WHO-DD]

Common Name

English

FEMA NO. 4223

Code

English

(CARBOXYMETHYL)TRIMETHYLAMMONIUM

Systematic Name

English

BETAINE [HSDB]

Common Name

English

BETAINE ANHYDROUS

Common Name

English

BETAINE [MART.]

Common Name

English

BETAINE [USP-RS]

Common Name

English

BETAINE [INCI]

Common Name

English

BETAINE [VANDF]

Common Name

English

NSC-166511

Code

English

TRIMETHYLGLYCINE

Systematic Name

English

ABROMINE

Common Name

English

BETAINE [JAN]

Common Name

English

BETAINE, ANHYDROUS

Common Name

English

BETAINE [FHFI]

Common Name

English

BETAINE ANHYDROUS [EMA EPAR]

Common Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

103669