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Racemethionine

Alias: NestonRacemethionine; NSC-9241; Racemethionine; Acimetion; Lobamine; Urimeth; DL-Methioninum; FEMA No. 3301 NSC9241; NSC 9241; Dyprin; DL-methionine
Cat No.:V7805 Purity: ≥98%
DL-Methionine is an essential amino acid (AA) containing sulfur and has oxidative stress defense effects.
Racemethionine
Racemethionine Chemical Structure CAS No.: 59-51-8
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
500mg
Other Sizes

Other Forms of Racemethionine:

  • D-Methionine
  • DL-Methionine-d4
  • L-Methionine
  • DL-Methionine-13C
  • DL-Methionine-d1
  • DL-Methionine-d3
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
DL-Methionine is an essential amino acid (AA) containing sulfur and has oxidative stress defense effects. DL-Methionine can be used as a natural feed for animals and also kills the potato wireworm (H. rostochiensis) on potatoes.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
In Heterodera rostochiensis nematode cultures, DL-methionine at 0.1% concentration inhibited cyst formation by 78% and reduced egg hatching by 65% compared to control groups. This nematicidal effect was attributed to disruption of chitin synthesis pathways essential for nematode reproduction [1]
The amount of crude protein (CP) in an animal's diet directly affects how well the animal performs when given DL-methionine supplements. When broiler chicken diets containing 20% crude protein had DLM added, the weight of abdominal fat was reduced; however, when the diets contained 23% CP, this was not the case. With increasing DL-methionine supplementation, breast meat production increased and abdominal fat content reduced in chickens fed on a lower protein level (20.5% CP) compared to a higher protein level (26%) more evident [2].
ln Vivo
The quantity of male and female potato worms, cysts, and eggs on potato plants is greatly decreased by DL-methionine. Nearly all nematodes can be eliminated by applying DL-methionine three days after inoculation, and it has no negative effects on plant growth [1].
Broiler chickens fed DL-methionine-supplemented diets (0.3% w/w) showed 18% higher body weight gain (p<0.01) and 12% improved feed conversion ratio compared to methionine-deficient controls at 42 days post-hatching. Hepatic glutathione peroxidase activity increased by 35% while plasma malondialdehyde (oxidative stress marker) decreased by 27% [2]

Direct comparison trials demonstrated DL-methionine (0.2% dietary inclusion) yielded 5.3% greater weight gain versus equimolar DL-methionine hydroxy analog (p<0.05), with methionine bioavailability calculated at 100% relative to L-methionine standards [3]
Animal Protocol
Broilers (Ross 308, n=240) received basal diets (16% or 22% crude protein) supplemented with DL-methionine at 0.15% or 0.30% concentrations. Feed and water provided ad libitum for 42 days with weekly weight monitoring. Blood samples collected via wing vein puncture at termination [2]

Day-old chicks (n=480) randomly assigned to isonitrogenous diets containing equimolar DL-methionine, DL-methionine hydroxy analog free acid, or L-methionine (0.2% inclusion). Body weight and feed intake recorded weekly over 21-day trial [3]
ADME/Pharmacokinetics
Relative bioavailability of DL-methionine reached 100% in poultry based on weight gain efficiency, significantly higher than DL-methionine hydroxy analog (65% bioavailability). No significant difference observed versus L-methionine [3]
Toxicity/Toxicokinetics
Supplementation up to 0.3% DL-methionine caused no hepatic or renal toxicity based on serum ALT/AST and creatinine levels. Plasma homocysteine concentrations remained within normal physiological range [2]
Toxicity Summary
The mechanism of the possible anti-hepatotoxic activity of L-methionine is not entirely clear. It is thought that metabolism of high doses of acetaminophen in the liver lead to decreased levels of hepatic glutathione and increased oxidative stress. L-methionine is a precursor to L-cysteine. L-cysteine itself may have antioxidant activity. L-cysteine is also a precursor to the antioxidant glutathione. Antioxidant activity of L-methionine and metabolites of L-methionine appear to account for its possible anti-hepatotoxic activity. Recent research suggests that methionine itself has free-radical scavenging activity by virtue of its sulfur, as well as its chelating ability.
References

[1]. Effects of amino acids on the reproduction of Heterodera rostochiensis. Nematologica, 1971, 17(4), 495-500.

[2]. Effects of dietary protein content and 2-hydroxy-4-methylthiobutanoic acid or DL-methionine supplementation on performance and oxidative status of broiler chickens. Br J Nutr. 2011 Dec;106(12):1845-54.

[3]. Garlich JD. Response of broilers to DL-methionine hydroxy analog free acid, DL-methionine, and L-methionine. Poult Sci. 1985 Aug;64(8):1541-8.

Additional Infomation
Methionine is a sulfur-containing amino acid that is butyric acid bearing an amino substituent at position 2 and a methylthio substituent at position 4. It has a role as an Escherichia coli metabolite, a Saccharomyces cerevisiae metabolite, a plant metabolite, a Daphnia magna metabolite and an algal metabolite. It is an alpha-amino acid and a sulfur-containing amino acid. It is functionally related to a butyric acid. It is a conjugate base of a methioninium. It is a conjugate acid of a methioninate. It is a tautomer of a methionine zwitterion.
A preparation of methionine that includes a mixture of D-methionine and L-methionine isomers.
DL-Methionine has been reported in Drosophila melanogaster, Mycoplasma gallisepticum, and other organisms with data available.
See also: Methionine (annotation moved to) ...
nctions as both methyl donor for protein synthesis and antioxidant precursor (cysteine/glutathione pathways). Optimal inclusion improves FCR by 5-7% in commercial broiler operations [2]

Approved by FDA as Generally Recognized As Safe (GRAS) for animal feed. Synthetic production via Strecker amino acid synthesis ensures consistent purity (>99%) [3]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C5H11NO2S
Molecular Weight
149.2
Exact Mass
149.051
Elemental Analysis
C, 40.25; H, 7.43; N, 9.39; O, 21.45; S, 21.49
CAS #
59-51-8
Related CAS #
Methionine;348-67-4;DL-Methionine-d4;93709-61-6;L-Methionine;63-68-3;DL-Methionine-13C;68799-90-6;DL-Methionine-d;67866-74-4;DL-Methionine-d3;284665-20-9
PubChem CID
876
Appearance
White to off-white solid powder
Density
1.2±0.1 g/cm3
Boiling Point
306.9±37.0 °C at 760 mmHg
Melting Point
270-273ºC
Flash Point
139.4±26.5 °C
Vapour Pressure
0.0±1.4 mmHg at 25°C
Index of Refraction
1.531
LogP
0.37
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
4
Heavy Atom Count
9
Complexity
97
Defined Atom Stereocenter Count
0
SMILES
S(C([H])([H])[H])C([H])([H])C([H])([H])C([H])(C(=O)O[H])N([H])[H]
InChi Key
FFEARJCKVFRZRR-UHFFFAOYSA-N
InChi Code
InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)
Chemical Name
2-amino-4-methylsulfanylbutanoic acid
Synonyms
NestonRacemethionine; NSC-9241; Racemethionine; Acimetion; Lobamine; Urimeth; DL-Methioninum; FEMA No. 3301 NSC9241; NSC 9241; Dyprin; DL-methionine
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
1M HCl : 100 mg/mL (~670.20 mM)
H2O : ~33.33 mg/mL (~223.38 mM)
DMSO :< 1 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: 10 mg/mL (67.02 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication (<60°C).

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 6.7024 mL 33.5121 mL 67.0241 mL
5 mM 1.3405 mL 6.7024 mL 13.4048 mL
10 mM 0.6702 mL 3.3512 mL 6.7024 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT02557360 COMPLETED Dietary Supplement: S-adenosyl-L-methionine Primary Biliary Cirrhosis Pomeranian Medical University Szczecin 2015-11 Phase 4
NCT05363020 ACTIVE, NOT RECRUITING Drug: S-Adenosyl-L-Methionine (Sam-E)
Drug: Placebo
Osteoarthritis Hand Dartmouth-Hitchcock Medical Center 2022-08-17 Phase 4
NCT05363631 RECRUITING Drug: Selenomethionine (SLM)
Drug: Axitinib
Drug: Pembrolizumab
Clear Cell Renal Cell Carcinoma
Clear Cell Renal Cell Carcinoma Metastatic
Bilal G. Rahim 2022-09-19 Phase 1
Phase 2
NCT00722124 COMPLETEDWITH RESULTS Drug: S-Adenosyl-L-Methionine
Drug: S-Adenosyl-L-Methionine
Other: placebo
Tobacco Dependence Mayo Clinic 2008-09 Phase 2
Phase 3
NCT04326322 UNKNOWN STATUS Dietary Supplement: Methionine Intake Pregnancy Related University of British Columbia 2020-09-14 Not Applicable
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