D-methionine

Names

[ CAS No. ]:
348-67-4

[ Name ]:
D-methionine

[Synonym ]:
R-Methionine
(R)-2-amino-4-(methylthio)butanoic acid
Methionine, D-
D-Methionin
d-Met
(2R)-2-amino-4-(methylsulfanyl)butanoic acid
(R)-methionine
D-Methionine
(R)-2-Amino-4-(methylmercapto)butyric acid (D-2-Amino-4-(methylthio)butanoic acid
EINECS 206-483-6
(2R)-2-amino-4-methylsulfanylbutanoic acid
H-D-Met-OH
MFCD00002622
H-D-Met-OEt.HCl
MRX-1024

Biological Activity

[Description]:

Methionine (MRX-1024) is an effective chemoprotective agent which can also inhibit the neuronal activity through GABAA receptor activation.

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> GABA Receptor

Signaling Pathways >> Neuronal Signaling >> GABA Receptor

Research Areas >> Cancer

Research Areas >> Neurological Disease

[Target]

GABAA receptor[1]

[In Vitro]

The incubation of human plasma with Methionine (D-methionine) and CP leads to the formation of a Pt-D-methionine complex independent of the order of addition. In plasma, an early CP hydrolysis product reacts with Methionine to form a 1:1 complex that is followed by the formation of a 2:1 compound at a later time point. The formation of these Pt-D-methionine species plays an important role in the processes by which Methionine protects mammalian organisms against CP-induced toxicities[2].

[In Vivo]

When Methionine (D-methionine) is administered along with cisplatin the cell density is 0.8±0.070 (SEM), significantly larger than in rats treated with only cisplatin (P<0.01) while not significantly different from controls or from animals treated only with D-methionine (P>0.05). When Methionine is administered alone the average cell density is 0.95±0.099 (SEM) and not significantly different from controls (P>0.05)[3].

[Cell Assay]

Plasma (2.0 mL) is spiked with 81 mL of the CP stock solution, incubated at 37°C for 30 min and then 20 mL of theMethionine (D-methionine) stock solution (40.7 mg/mL) is added. The obtained mixture is analyzed after 10 min and 50 min of incubation at 37°C[2].

[Animal admin]

Three sham controls receive 0.9% saline instead of cisplatin. Three rats receive only cisplatin. Another three rats receive Methionine (D-methionine) 30 minutes prior to treatment with cisplatin. Injection of Methionine prior to cisplatin treatment ensures that it is already taken up before cisplatin is applied. Finally, three rats are treated only with Methionine. All 12 rats are sacrificed at day 7 post-treatment. For prescreening, two further rats are treated with cisplatin alone and sacrificed 2 or 21 days later. All rats are hydrated with 0.9% saline[3].

[References]

[1]. Wu C, et al. Antioxidants L-carnitine and D-methionine modulate neuronal activity through GABAergic inhibition. J Neural Transm (Vienna). 2014 Jul;121(7):683-93.

[2]. Sooriyaarachchi M, et al. Chemoprotection by D-methionine against cisplatin-induced side-effects: insight from in vitrostudies using human plasma. Metallomics. 2014 Mar;6(3):532-41.

[3]. Hinduja S, et al. D-methionine protects against cisplatin-induced neurotoxicity in the hippocampus of the adult rat. Neurotox Res. 2015 Apr;27(3):199-204.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
306.9±37.0 °C at 760 mmHg

[ Melting Point ]:
273-275ºC

[ Molecular Formula ]:
C₅H₁₁NO₂S

[ Molecular Weight ]:
149.211

[ Flash Point ]:
139.4±26.5 °C

[ Exact Mass ]:
149.051056

[ PSA ]:
88.62000

[ LogP ]:
0.37

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.531

[ Storage condition ]:
2~8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: PD0455000

CHEMICAL NAME :: Methionine, D-

CAS REGISTRY NUMBER :: 348-67-4

LAST UPDATED :: 199709

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C5-H11-N-O2-S

MOLECULAR WEIGHT :: 149.23

WISWESSER LINE NOTATION :: QVYZ2S1 -D

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 5223 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Lungs, Thorax, or Respiration - dyspnea Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: ABBIA4 Archives of Biochemistry and Biophysics. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.31- 1951- Volume(issue)/page/year: 64,319,1956 *** REVIEWS *** TOXICOLOGY REVIEW JAFCAU Journal of Agricultural and Food Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB 57136, West End Stn., Washington, DC 20037) V.1- 1953- Volume(issue)/page/year: 22,2,1974

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R33

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
PD0455000

[ HS Code ]:
2930400000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2930909090

[ Summary ]:
2930909090. other organo-sulphur compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

Ectodermal-neural cortex 1 down-regulates Nrf2 at the translational level.

PLoS ONE 4(5) , e5492, (2009)

The transcription factor Nrf2 is the master regulator of a cellular defense mechanism against environmental insults. The Nrf2-mediated antioxidant response is accomplished by the transcription of a ba...

Antioxidants L-carnitine and D-methionine modulate neuronal activity through GABAergic inhibition.

J. Neural Transm. Gen. Sect. 121(7) , 683-93, (2014)

Antioxidants are well known for their neuroprotective properties against reactive oxygen species in cortical neurons and auditory cells. We recently identified L-carnitine and D-methionine to be among...

D-methionine (D-met) significantly rescues noise-induced hearing loss: timing studies.

Hear. Res. 282 , 138-144, (2011)

We have previously reported rescue from noise-induced auditory brainstem response (ABR) threshold shifts with d-methionine (d-met) administration 1 h after noise exposure. The present study investigat...