U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C5H11NO2S
Molecular Weight 149.211
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RACEMETHIONINE

SMILES

CSCCC(N)C(O)=O

InChI

InChIKey=FFEARJCKVFRZRR-UHFFFAOYSA-N
InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)

HIDE SMILES / InChI
DL-Methionine is a racemic form of the respective sulfur aminoacid. DL-Methionine participates in synthesis of tissue proteins, vitamins, enzymes and hormones taking part in nitrogen, carbohydrate and fat metabolisms, and it is the important source of methyl groups for synthesis of all nucleic acids, as well as the sulfur source for sulfonic compounds. Methionine is used to prevent liver damage in acetaminophen (Tylenol) poisoning. It is also used for increasing the acidity of urine, treating liver disorders, and improving wound healing. Other uses include treating depression, alcoholism, allergies, asthma, copper poisoning, radiation side effects, schizophrenia, drug withdrawal, and Parkinson's disease. It is also used as a food additive in livestock to boost performance. DL-Methionin is the first limiting amino acid in poultry, and probably also in high-yielding cows, and is the second or third limiting amino acid in pigs fed conventional diets.

Approval Year

Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Involvement of pro-enkephalin-derived peptides in immunity.
2001 Apr
Elevation of asymmetrical dimethylarginine may mediate endothelial dysfunction during experimental hyperhomocyst(e)inaemia in humans.
2001 Feb
Effects of acute methionine loading and vitamin C on endogenous fibrinolysis, endothelium-dependent vasomotion and platelet aggregation.
2001 Feb
Rapid acquisition of entire DNA polymerase gene of a novel herpesvirus from green turtle fibropapilloma by a genomic walking technique.
2001 Feb
In situ kinetic characterization of methylthioadenosine transport by the adenosine transporter (P2) of the African Trypanosoma brucei brucei and Trypanosoma brucei rhodesiense.
2001 Feb 15
A mutation in alpha-tropomyosin(slow) affects muscle strength, maturation and hypertrophy in a mouse model for nemaline myopathy.
2001 Feb 15
Trp 346 and Leu 352 residues in protective antigen are required for the expression of anthrax lethal toxin activity.
2001 Feb 16
Intestinal disappearance and mesenteric and portal appearance of amino acids in dairy cows fed ruminally protected methionine.
2001 Jan
Lack of association between the Met196Arg polymorphism in the TNFR2 gene and autoimmune diseases accompanied by vasculitis including SLE in Japanese.
2001 Jan
Impaired response to interferon-gamma in activated macrophages due to tyrosine nitration of STAT1 by endogenous nitric oxide.
2001 Jan
Acute methionine loading does not alter arterial stiffness in humans.
2001 Jan
Maternal plasma homocysteine levels in women with preterm premature rupture of membranes.
2001 Jan
An in vivo study of ovine placental transport of essential amino acids.
2001 Jan
Cloning and functional analysis of the Sry-related HMG box gene, Sox18.
2001 Jan 10
Selective degradation of oxidized calmodulin by the 20 S proteasome.
2001 Jan 12
Increased susceptibility to Kuru of carriers of the PRNP 129 methionine/methionine genotype.
2001 Jan 15
Thromboangiitis obliterans (Buerger's disease).
2001 Jan 18
Evaluation of lysine and methionine production in some Lactobacilli and yeasts from ogi.
2001 Jan 22
The effects of processing methods on the levels of lysine, methionine and the general acceptability of ogi processed using starter cultures.
2001 Jan 22
Eukaryotic translation initiation factor 5 (eIF5) acts as a classical GTPase-activator protein.
2001 Jan 9
Crystallization and preliminary X-ray crystallographic studies of recombinant human betaine-homocysteine S-methyltransferase.
2001 Mar
Synthesis of active high mannose-type lipoprotein lipase in human adipose tissues.
2001 Mar
Evidence against oxidative stress as mechanism of endothelial dysfunction in methionine loading model.
2001 Mar
COMT-dependent protection of dopaminergic neurons by methionine, dimethionine and S-adenosylmethionine (SAM) against L-dopa toxicity in vitro.
2001 Mar 2
Prostaglandin endoperoxide H synthase-1: the functions of cyclooxygenase active site residues in the binding, positioning, and oxygenation of arachidonic acid.
2001 Mar 30
Transporters on demand: intrahepatic pools of canalicular ATP binding cassette transporters in rat liver.
2001 Mar 9
Uptake of tritiated thymidine, deoxyglucose and methionine in three lung cancer cell lines: deoxyglucose uptake mirrors tritiated thymidine uptake.
2001 Mar-Apr
Patents

Sample Use Guides

For acetaminophen (Tylenol) poisoning: 2.5 grams of methionine every 4 hours for 4 doses to prevent liver damage and death. Methionine must be given within 10 hours of taking the acetaminophen.
Route of Administration: Oral
Name Type Language
RACEMETHIONINE
USAN   USP-RS   VANDF  
USAN  
Official Name English
METHIONINE DL-FORM
MI  
Common Name English
DL-2-AMINO-4-(METHYLTHIO)-BUTYRIC ACID
Common Name English
LOBAMINE
Common Name English
DL-METHIONINE [WHO-IP]
Common Name English
DL-METHIONINE [EP MONOGRAPH]
Common Name English
RACEMETHIONINE [USAN]
Common Name English
D,L-METHIONINE
FHFI  
Common Name English
D,L-METHIONINE [FHFI]
Common Name English
DL-METHIONINE [JAN]
Common Name English
DL-METHIONINE [FCC]
Common Name English
DL-METHIONINE [EP IMPURITY]
Common Name English
DL-METHIONINE
EP   FCC   JAN   MART.   WHO-DD   WHO-IP  
Systematic Name English
DL-METHIONINE [MART.]
Common Name English
NSC-9241
Code English
RACEMETHIONINE [USP-RS]
Common Name English
PEDAMETH
Brand Name English
FEMA NO. 3301
Code English
Dl-methionine [WHO-DD]
Common Name English
METHIONINE DL-FORM [MI]
Common Name English
ACIMETION
Common Name English
DL-METHIONINUM [WHO-IP LATIN]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 172.320
Created by admin on Fri Dec 15 15:01:06 GMT 2023 , Edited by admin on Fri Dec 15 15:01:06 GMT 2023
JECFA EVALUATION DL-METHIONINE
Created by admin on Fri Dec 15 15:01:06 GMT 2023 , Edited by admin on Fri Dec 15 15:01:06 GMT 2023
NCI_THESAURUS C2081
Created by admin on Fri Dec 15 15:01:06 GMT 2023 , Edited by admin on Fri Dec 15 15:01:06 GMT 2023
DSLD 56 (Number of products:121)
Created by admin on Fri Dec 15 15:01:06 GMT 2023 , Edited by admin on Fri Dec 15 15:01:06 GMT 2023
Code System Code Type Description
RXCUI
9100
Created by admin on Fri Dec 15 15:01:06 GMT 2023 , Edited by admin on Fri Dec 15 15:01:06 GMT 2023
PRIMARY RxNorm
RS_ITEM_NUM
1643292
Created by admin on Fri Dec 15 15:01:06 GMT 2023 , Edited by admin on Fri Dec 15 15:01:06 GMT 2023
PRIMARY
PUBCHEM
876
Created by admin on Fri Dec 15 15:01:06 GMT 2023 , Edited by admin on Fri Dec 15 15:01:06 GMT 2023
PRIMARY
ChEMBL
CHEMBL274119
Created by admin on Fri Dec 15 15:01:06 GMT 2023 , Edited by admin on Fri Dec 15 15:01:06 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-432-1
Created by admin on Fri Dec 15 15:01:06 GMT 2023 , Edited by admin on Fri Dec 15 15:01:06 GMT 2023
PRIMARY
DRUG BANK
DB13972
Created by admin on Fri Dec 15 15:01:06 GMT 2023 , Edited by admin on Fri Dec 15 15:01:06 GMT 2023
PRIMARY
EVMPD
SUB13641MIG
Created by admin on Fri Dec 15 15:01:06 GMT 2023 , Edited by admin on Fri Dec 15 15:01:06 GMT 2023
PRIMARY
CAS
59-51-8
Created by admin on Fri Dec 15 15:01:06 GMT 2023 , Edited by admin on Fri Dec 15 15:01:06 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
RACEMETHIONINE
Created by admin on Fri Dec 15 15:01:06 GMT 2023 , Edited by admin on Fri Dec 15 15:01:06 GMT 2023
PRIMARY Description: An almost white, crystalline powder or small flakes. Solubility: Sparingly soluble in water; very slightly soluble in ethanol (~750 g/l) TS. It dissolves in dilute acids and in dilute solutions of the alkali hydroxides. Category: Antidote.Storage: DL-Methionine should be protected from light. Additional information: Melting temperature, about 270 ?C.Requirements: DL-Methionine contains not less than 99.0% and not more than 101.0% of C5H11NO2S, calculated with reference to the dried substance.
NSC
9241
Created by admin on Fri Dec 15 15:01:06 GMT 2023 , Edited by admin on Fri Dec 15 15:01:06 GMT 2023
PRIMARY
FDA UNII
73JWT2K6T3
Created by admin on Fri Dec 15 15:01:06 GMT 2023 , Edited by admin on Fri Dec 15 15:01:06 GMT 2023
PRIMARY
JECFA MONOGRAPH
1414
Created by admin on Fri Dec 15 15:01:06 GMT 2023 , Edited by admin on Fri Dec 15 15:01:06 GMT 2023
PRIMARY
EPA CompTox
DTXSID9020821
Created by admin on Fri Dec 15 15:01:06 GMT 2023 , Edited by admin on Fri Dec 15 15:01:06 GMT 2023
PRIMARY
MERCK INDEX
m7317
Created by admin on Fri Dec 15 15:01:06 GMT 2023 , Edited by admin on Fri Dec 15 15:01:06 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C84131
Created by admin on Fri Dec 15 15:01:06 GMT 2023 , Edited by admin on Fri Dec 15 15:01:06 GMT 2023
PRIMARY
SMS_ID
100000089062
Created by admin on Fri Dec 15 15:01:06 GMT 2023 , Edited by admin on Fri Dec 15 15:01:06 GMT 2023
PRIMARY
DAILYMED
73JWT2K6T3
Created by admin on Fri Dec 15 15:01:06 GMT 2023 , Edited by admin on Fri Dec 15 15:01:06 GMT 2023
PRIMARY
CHEBI
16811
Created by admin on Fri Dec 15 15:01:06 GMT 2023 , Edited by admin on Fri Dec 15 15:01:06 GMT 2023
PRIMARY