S-Adenosyl-L-methionine tosylate

• CAT Number: R065242
• CAS Number: 52248-03-0
• Molecular Formula: C22H30N6O8S2
• Molecular Weight: 570.64
• Purity: ≥95%
• Synonyms: [(3S)-3-amino-3-carboxypropyl]-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl]-methylsulfanium;4-methylbenzenesulfonate
• InChI: InChI=1S/C15H22N6O5S.C7H8O3S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21;1-6-2-4-7(5-3-6)11(8,9)10/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25);2-5H,1H3,(H,8,9,10)/t7-,8+,10+,11+,14+,27?;/m0./s1
• InChIKey: VHPOFDUCFKOUHV-XKGORWRGSA-N
• SMILES: CC1=CC=C(C=C1)S(=O)(=O)[O-].C[S+](CCC(C(=O)O)N)CC1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)O

S-Adenosyl-L-methionine tosylate is produced endogenously from methionine and ATP by action of the enzyme methionine adenosyltransferase and is an important orally active methyl group donor. S-Adenosyl-L-methionine tosylate is a dietary supplement with potent antidepressant and analgesic effects, and has the potential for liver disease and osteoarthritis research[1][2][3].
S-Adenosyl-L-methionine (Ademetionine) is involved in three main metabolic pathways: 1) methylation, as the principal source of methyl groups in the body; 2) transsulfuration, S-Adenosyl-L-methionine forms S-Adenosylhomocysteine (SAH) and then converted to homocysteine (Hcy) which can be converted to cystathionine then to cysteine and the sulfate (SO4) donated to other metabolic intermediates; and 3) aminopropylation, as S-Adenosyl-L-methionine plays an important role in the synthesis of polyamines which can eventually form and recycle methionine[2].?
In vitro studies using human articular chondrocytes have shown S-Adenosyl-L-methionine-induced increases in proteoglycan synthesis and proliferation rates in rabbits[2].
Mice lacking methionine adenosyltransferase 1a (Mat1a) have reduced hepatic S-Adenosyl-L-methionine levels and develop oxidative stress, steatohepatitis, and hepatocellular carcinoma (HCC).? However, injury and HCC also occur if hepatic S-Adenosyl-L-methionine level is excessive chronically. Thus a normal hepatic S-Adenosyl-L-methionine level is necessary to maintain liver health and prevent injury and HCC[3].

Reference

[1]. G M Bressa. et al. S-adenosyl-l-methionine (SAMe) as antidepressant: meta-analysis of clinical studies. Acta Neurol Scand Suppl. 1994;154:7-14.
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[2]. Wadie I Najm, et al. S-adenosyl methionine (SAMe) versus celecoxib for the treatment of osteoarthritis symptoms: a double-blind cross-over trial. [ISRCTN36233495]. BMC Musculoskelet Disord. 2004 Feb 26;5:6.
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[3]. Shelly C Lu, et al. S-adenosylmethionine in liver health, injury, and cancer. Physiol Rev. 2012 Oct;92(4):1515-42.
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