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Details

Stereochemistry RACEMIC
Molecular Formula C5H11NO2S
Molecular Weight 149.2126
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RACEMETHIONINE

SMILES

CSCCC(C(=O)O)N

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
Palladium(II) and platinum(II) complexes as synthetic peptidases.
2001
Involvement of pro-enkephalin-derived peptides in immunity.
2001 Apr
Bus, a bushy Arabidopsis CYP79F1 knockout mutant with abolished synthesis of short-chain aliphatic glucosinolates.
2001 Feb
Measurement of the synthesis, turnover, and assembly of alpha- and beta-erythroid and nonerythroid spectrins in cultured rat hippocampal neurons.
2001 Feb
Intestinal uptake of betaine in vitro and the distribution of methyl groups from betaine, choline, and methionine in the body of broiler chicks.
2001 Feb
A bifunctional dihydrofolate synthetase--folylpolyglutamate synthetase in Plasmodium falciparum identified by functional complementation in yeast and bacteria.
2001 Feb
The amino acid profiles of the whole plant and of four plant residues from temperate and tropical forages.
2001 Feb
[Inhibition effect of Amaryllidaceae alkaloids, lycorine and lycoricidinol on macrophage TNF-alpha production].
2001 Feb
Similarity between condensed phase and gas phase chemistry: fragmentation of peptides containing oxidized cysteine residues and its implications for proteomics.
2001 Feb
Vibrational spectroscopic study of DL-methionine dihydrogen phosphate.
2001 Feb
Lowered weight gain during pregnancy and risk of neural tube defects among offspring.
2001 Feb
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
Is there a role of cyclosporine A on total homocysteine export from human renal proximal tubular epithelial cells?
2001 Feb
Homocysteine metabolism in renal failure.
2001 Feb
The folate cycle and disease in humans.
2001 Feb
Therapeutic targets in radiotherapy.
2001 Feb 1
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
Trp 346 and Leu 352 residues in protective antigen are required for the expression of anthrax lethal toxin activity.
2001 Feb 16
Extracellular amino acid profiles in the paraventricular nucleus of the rat hypothalamus are influenced by diet composition.
2001 Feb 23
Steroidogenic acute regulatory protein expression is dependent upon post-translational effects of cAMP-dependent protein kinase A.
2001 Feb 28
Orientations of Tyr 21 and Tyr 24 in the capsid of filamentous virus Ff determined by polarized Raman spectroscopy.
2001 Feb 6
[Homocysteine, endothelial dysfunction and cardiovascular risk: pathomechanisms and therapeutic options].
2001 Jan
Intestinal disappearance and mesenteric and portal appearance of amino acids in dairy cows fed ruminally protected methionine.
2001 Jan
Retarded myelination in the lumbar spinal cord of piglets born with spread-leg syndrome.
2001 Jan
Near-infrared reflectance spectroscopy enables the fast and accurate prediction of the essential amino acid contents in soy, rapeseed meal, sunflower meal, peas, fishmeal, meat meal products, and poultry meal.
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
Identification and characterization of novel chromogranin B-derived peptides from porcine chromaffin granules by liquid chromatography/electrospray tandem MS.
2001 Jan
Characterization of promoter region and genomic structure of the murine and human genes encoding Src like adapter protein.
2001 Jan 10
Cloning and functional analysis of the Sry-related HMG box gene, Sox18.
2001 Jan 10
Sec63p and Kar2p are required for the translocation of SRP-dependent precursors into the yeast endoplasmic reticulum in vivo.
2001 Jan 15
Thromboangiitis obliterans (Buerger's disease).
2001 Jan 18
Comparison of Vif sequences from diverse geographical isolates of HIV type 1 and SIV(cpz) identifies substitutions common to subtype C isolates and extensive variation in a proposed nuclear transport inhibition signal.
2001 Jan 20
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
Electronic characterization of the oxidized state of the blue copper protein rusticyanin by 1H NMR: is the axial methionine the dominant influence for the high redox potential?
2001 Jan 23
Mapping the energy surface for the folding reaction of the coiled-coil peptide GCN4-p1.
2001 Jan 23
The additional methionine residue at the N-terminus of bacterially expressed human interleukin-2 affects the interaction between the N- and C-termini.
2001 Jan 30
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
Structure of the M148Q mutant of rusticyanin at 1.5 A: a model for the copper site of stellacyanin.
2001 Mar
Synthesis of active high mannose-type lipoprotein lipase in human adipose tissues.
2001 Mar
Inhibitory effect of reactive oxygen species on angiotensin I-converting enzyme (kininase II).
2001 Mar
The effects of oral methionine and homocysteine on endothelial function.
2001 Mar
Evidence against oxidative stress as mechanism of endothelial dysfunction in methionine loading model.
2001 Mar
Kinetics of the reactions of hypochlorous acid and amino acid chloramines with thiols, methionine, and ascorbate.
2001 Mar 1
Relative reactivities of N-chloramines and hypochlorous acid with human plasma constituents.
2001 Mar 1
Thermodynamics of the helix-coil transition: Binding of S15 and a hybrid sequence, disulfide stabilized peptide to the S-protein.
2001 Mar 1
COMT-dependent protection of dopaminergic neurons by methionine, dimethionine and S-adenosylmethionine (SAM) against L-dopa toxicity in vitro.
2001 Mar 2
Axon terminals containing CGRP-immunoreactivity form synapses with CRF- and Met-enkephalin-immunopositive neurons in the laterodorsal division of the bed nucleus of the stria terminalis in the rat.
2001 Mar 2
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   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-METHIONINE [EP]
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 Jun 25 21:10:47 UTC 2021 , Edited by admin on Fri Jun 25 21:10:47 UTC 2021
JECFA EVALUATION DL-METHIONINE
Created by admin on Fri Jun 25 21:10:47 UTC 2021 , Edited by admin on Fri Jun 25 21:10:47 UTC 2021
NCI_THESAURUS C2081
Created by admin on Fri Jun 25 21:10:47 UTC 2021 , Edited by admin on Fri Jun 25 21:10:47 UTC 2021
DSLD 56 (Number of products:121)
Created by admin on Fri Jun 25 21:10:47 UTC 2021 , Edited by admin on Fri Jun 25 21:10:47 UTC 2021
Code System Code Type Description
RXCUI
9100
Created by admin on Fri Jun 25 21:10:47 UTC 2021 , Edited by admin on Fri Jun 25 21:10:47 UTC 2021
PRIMARY RxNorm
PUBCHEM
876
Created by admin on Fri Jun 25 21:10:47 UTC 2021 , Edited by admin on Fri Jun 25 21:10:47 UTC 2021
PRIMARY
ChEMBL
CHEMBL274119
Created by admin on Fri Jun 25 21:10:47 UTC 2021 , Edited by admin on Fri Jun 25 21:10:47 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-432-1
Created by admin on Fri Jun 25 21:10:47 UTC 2021 , Edited by admin on Fri Jun 25 21:10:47 UTC 2021
PRIMARY
DRUG BANK
DB13972
Created by admin on Fri Jun 25 21:10:47 UTC 2021 , Edited by admin on Fri Jun 25 21:10:47 UTC 2021
PRIMARY
EVMPD
SUB13641MIG
Created by admin on Fri Jun 25 21:10:47 UTC 2021 , Edited by admin on Fri Jun 25 21:10:47 UTC 2021
PRIMARY
CAS
59-51-8
Created by admin on Fri Jun 25 21:10:47 UTC 2021 , Edited by admin on Fri Jun 25 21:10:47 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
RACEMETHIONINE
Created by admin on Fri Jun 25 21:10:47 UTC 2021 , Edited by admin on Fri Jun 25 21:10:47 UTC 2021
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.
FDA UNII
73JWT2K6T3
Created by admin on Fri Jun 25 21:10:47 UTC 2021 , Edited by admin on Fri Jun 25 21:10:47 UTC 2021
PRIMARY
EPA CompTox
59-51-8
Created by admin on Fri Jun 25 21:10:47 UTC 2021 , Edited by admin on Fri Jun 25 21:10:47 UTC 2021
PRIMARY
MERCK INDEX
M7317
Created by admin on Fri Jun 25 21:10:47 UTC 2021 , Edited by admin on Fri Jun 25 21:10:47 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C84131
Created by admin on Fri Jun 25 21:10:47 UTC 2021 , Edited by admin on Fri Jun 25 21:10:47 UTC 2021
PRIMARY
USP_CATALOG
1643292
Created by admin on Fri Jun 25 21:10:47 UTC 2021 , Edited by admin on Fri Jun 25 21:10:47 UTC 2021
PRIMARY USP-RS