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Details

Stereochemistry ACHIRAL
Molecular Formula C5H12NO2.Cl
Molecular Weight 153.607
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Betaine hydrochloride

SMILES

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

InChI

InChIKey=HOPSCVCBEOCPJZ-UHFFFAOYSA-N
InChI=1S/C5H11NO2.ClH/c1-6(2,3)4-5(7)8;/h4H2,1-3H3;1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C5H11NO2
Molecular Weight 117.1463
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

1996
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.456 mM
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
12.528 mM × h
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
41.17 h
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
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

Doses

DosePopulationAdverse 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:
unhealthy, adult
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Isolation of glycine betaine and proline betaine from human urine. Assessment of their role as osmoprotective agents for bacteria and the kidney.
1987 Mar
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
Cerebrospinal fluid and plasma total homocysteine and related metabolites in children with cystathionine beta-synthase deficiency: the effect of treatment.
1997 Nov
Simple method for the routine determination of betaine and N,N-dimethylglycine in blood and urine.
1998 Sep
An open-label, 24-week pilot study of the methyl donor betaine in Alzheimer disease patients.
2001 Jul-Sep
Determination of choline, betaine, and dimethylglycine in plasma by a high-throughput method based on normal-phase chromatography-tandem mass spectrometry.
2003 Feb
Homocysteine-betaine interactions in a murine model of 5,10-methylenetetrahydrofolate reductase deficiency.
2003 Mar
Betaine. Monograph.
2003 May
Muscle metabolites, detected in urine by proton spectroscopy, correlate with disease damage in juvenile idiopathic inflammatory myopathies.
2005 Aug 15
Consideration of betaine and one-carbon sources of N5-methyltetrahydrofolate for use in homocystinuria and neural tube defects.
2007 Apr
Betaine-homocysteine S-methyltransferase-2 is an S-methylmethionine-homocysteine methyltransferase.
2008 Apr 4
Characteristics of transport of selenoamino acids by epithelial amino acid transporters.
2009 Feb 12
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
Mechanism for prevention of alcohol-induced liver injury by dietary methyl donors.
2010 May
Effects of betaine on lipopolysaccharide-induced memory impairment in mice and the involvement of GABA transporter 2.
2011 Nov 4
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
Betaine supplementation protects against renal injury induced by cadmium intoxication in rats: role of oxidative stress and caspase-3.
2014 Mar
Proteomics analysis of altered cellular metabolism induced by insufficient copper level.
2014 Nov 10
5-Methyl phenazine-1-carboxylic acid: a novel bioactive metabolite by a rhizosphere soil bacterium that exhibits potent antimicrobial and anticancer activities.
2015 Apr 25
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
Betanin reduces the accumulation and cross-links of collagen in high-fructose-fed rat heart through inhibiting non-enzymatic glycation.
2015 Feb 5
Regulation of signal transducer and activator of transcription 3 and apoptotic pathways by betaine attenuates isoproterenol-induced acute myocardial injury in rats.
2015 May
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:23:20 GMT 2023
Edited
by admin
on Fri Dec 15 15:23:20 GMT 2023
Record UNII
JK8U8K4D6K
Record Status Validated (UNII)
Record Version
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Name Type Language
Betaine hydrochloride
MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common Name English
BETAINE HYDROCHLORIDE [VANDF]
Common Name English
BETAINUM MURIATICUM
HPUS  
Common Name English
NSC-32191
Code English
BETAINUM MURIATICUM [HPUS]
Common Name English
BETAINE HYDROCHLORIDE [MART.]
Common Name English
NSC-3976
Code English
METHANAMINIUM, 1-CARBOXY-N,N,N-TRIMETHYL-, CHLORIDE
Systematic Name English
Betaine hydrochloride [WHO-DD]
Common Name English
BETAINE HYDROCHLORIDE [USP-RS]
Common Name English
(CARBOXYMETHYL)TRIMETHYLAMMONIUM CHLORIDE
Systematic Name English
BETAINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
BETAINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
BETAINE HCL
Common Name English
CYSTADANE
Brand Name English
BETAINE HYDROCHLORIDE [USP IMPURITY]
Common Name English
Classification Tree Code System Code
WHO-ATC A09AB02
Created by admin on Fri Dec 15 15:23:20 GMT 2023 , Edited by admin on Fri Dec 15 15:23:20 GMT 2023
EMA ASSESSMENT REPORTS CYSTADANE (AUTHORIZED: HOMOCYSTINURIA)
Created by admin on Fri Dec 15 15:23:20 GMT 2023 , Edited by admin on Fri Dec 15 15:23:20 GMT 2023
DSLD 19 (Number of products:1116)
Created by admin on Fri Dec 15 15:23:20 GMT 2023 , Edited by admin on Fri Dec 15 15:23:20 GMT 2023
WHO-VATC QA09AB02
Created by admin on Fri Dec 15 15:23:20 GMT 2023 , Edited by admin on Fri Dec 15 15:23:20 GMT 2023
CFR 21 CFR 310.540
Created by admin on Fri Dec 15 15:23:20 GMT 2023 , Edited by admin on Fri Dec 15 15:23:20 GMT 2023
Code System Code Type Description
RXCUI
81965
Created by admin on Fri Dec 15 15:23:20 GMT 2023 , Edited by admin on Fri Dec 15 15:23:20 GMT 2023
PRIMARY RxNorm
EVMPD
SUB13059MIG
Created by admin on Fri Dec 15 15:23:20 GMT 2023 , Edited by admin on Fri Dec 15 15:23:20 GMT 2023
PRIMARY
NCI_THESAURUS
C82301
Created by admin on Fri Dec 15 15:23:20 GMT 2023 , Edited by admin on Fri Dec 15 15:23:20 GMT 2023
PRIMARY
RS_ITEM_NUM
1065709
Created by admin on Fri Dec 15 15:23:20 GMT 2023 , Edited by admin on Fri Dec 15 15:23:20 GMT 2023
PRIMARY
EPA CompTox
DTXSID0044446
Created by admin on Fri Dec 15 15:23:20 GMT 2023 , Edited by admin on Fri Dec 15 15:23:20 GMT 2023
PRIMARY
MERCK INDEX
m2451
Created by admin on Fri Dec 15 15:23:20 GMT 2023 , Edited by admin on Fri Dec 15 15:23:20 GMT 2023
PRIMARY Merck Index
CAS
590-46-5
Created by admin on Fri Dec 15 15:23:20 GMT 2023 , Edited by admin on Fri Dec 15 15:23:20 GMT 2023
PRIMARY
NCI_THESAURUS
C1505
Created by admin on Fri Dec 15 15:23:20 GMT 2023 , Edited by admin on Fri Dec 15 15:23:20 GMT 2023
CONCEPT Dietary Supplement
SMS_ID
100000092033
Created by admin on Fri Dec 15 15:23:20 GMT 2023 , Edited by admin on Fri Dec 15 15:23:20 GMT 2023
PRIMARY
NSC
3976
Created by admin on Fri Dec 15 15:23:20 GMT 2023 , Edited by admin on Fri Dec 15 15:23:20 GMT 2023
PRIMARY
PUBCHEM
11545
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PRIMARY
ECHA (EC/EINECS)
209-683-1
Created by admin on Fri Dec 15 15:23:20 GMT 2023 , Edited by admin on Fri Dec 15 15:23:20 GMT 2023
PRIMARY
DRUG BANK
DBSALT001448
Created by admin on Fri Dec 15 15:23:20 GMT 2023 , Edited by admin on Fri Dec 15 15:23:20 GMT 2023
PRIMARY
FDA UNII
JK8U8K4D6K
Created by admin on Fri Dec 15 15:23:20 GMT 2023 , Edited by admin on Fri Dec 15 15:23:20 GMT 2023
PRIMARY
DAILYMED
JK8U8K4D6K
Created by admin on Fri Dec 15 15:23:20 GMT 2023 , Edited by admin on Fri Dec 15 15:23:20 GMT 2023
PRIMARY
ChEMBL
CHEMBL95889
Created by admin on Fri Dec 15 15:23:20 GMT 2023 , Edited by admin on Fri Dec 15 15:23:20 GMT 2023
PRIMARY
NSC
32191
Created by admin on Fri Dec 15 15:23:20 GMT 2023 , Edited by admin on Fri Dec 15 15:23:20 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY