Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C5H11NO2.H2O |
| Molecular Weight | 135.1616 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.C[N+](C)(C)CC([O-])=O
InChI
InChIKey=NJZRLXNBGZBREL-UHFFFAOYSA-N
InChI=1S/C5H11NO2.H2O/c1-6(2,3)4-5(7)8;/h4H2,1-3H3;1H2
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 |
|---|---|---|---|---|
| Primary | CYSTADANE Approved UseCystadane 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 Date1996 |
Cmax
| 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 |
T1/2
| 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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| The clinical potential of ademetionine (S-adenosylmethionine) in neurological disorders. | 1994 Aug |
|
| Strychnine-dependent allodynia in the urethane-anesthetized rat is segmentally distributed and prevented by intrathecal glycine and betaine. | 1995 Dec |
|
| Betaine supplementation decreases plasma homocysteine concentrations but does not affect body weight, body composition, or resting energy expenditure in human subjects. | 2002 Nov |
|
| Carbon tetrachloride-induced nephrotoxicity and protective effect of betaine in Sprague-Dawley rats. | 2003 Aug |
|
| Determination of choline, betaine, and dimethylglycine in plasma by a high-throughput method based on normal-phase chromatography-tandem mass spectrometry. | 2003 Feb |
|
| Betaine. Monograph. | 2003 May |
|
| Muscle metabolites, detected in urine by proton spectroscopy, correlate with disease damage in juvenile idiopathic inflammatory myopathies. | 2005 Aug 15 |
|
| Betaine suppresses proinflammatory signaling during aging: the involvement of nuclear factor-kappaB via nuclear factor-inducing kinase/IkappaB kinase and mitogen-activated protein kinases. | 2005 Oct |
|
| Mechanism of the inhibitory effect of zwitterionic drugs (levofloxacin and grepafloxacin) on carnitine transporter (OCTN2) in Caco-2 cells. | 2006 Nov |
|
| Maternal methyl supplements increase offspring DNA methylation at Axin Fused. | 2006 Sep |
|
| Consideration of betaine and one-carbon sources of N5-methyltetrahydrofolate for use in homocystinuria and neural tube defects. | 2007 Apr |
|
| Alleviation of dimethylnitrosamine-induced liver injury and fibrosis by betaine supplementation in rats. | 2009 Feb 12 |
|
| Characteristics of transport of selenoamino acids by epithelial amino acid transporters. | 2009 Feb 12 |
|
| S-Adenosylhomocysteine increases beta-amyloid formation in BV-2 microglial cells by increased expressions of beta-amyloid precursor protein and presenilin 1 and by hypomethylation of these gene promoters. | 2009 Jul |
|
| 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 |
|
| Identification of a novel organic anion transporter mediating carnitine transport in mouse liver and kidney. | 2010 |
|
| Chemical chaperones improve protein secretion and rescue mutant factor VIII in mice with hemophilia A. | 2012 |
|
| Wilson's disease: changes in methionine metabolism and inflammation affect global DNA methylation in early liver disease. | 2013 Feb |
|
| Survival and psychomotor development with early betaine treatment in patients with severe methylenetetrahydrofolate reductase deficiency. | 2014 Feb |
|
| The organic osmolyte betaine induces keratin 2 expression in rat epidermal keratinocytes - A genome-wide study in UVB irradiated organotypic 3D cultures. | 2015 Dec 25 |
Patents
Sample Use Guides
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
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.
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590-47-6
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m2451
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83815
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TPU0ITR2BR
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SUB13060MIG
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DTXSID7049421
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100000077392
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209-684-7
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
