S-Adenosyl-L-methionine tosylate is endogenously produced from methionine and ATP through the action of methionine adenosyltransferase and is an important orally bioactive methyl donor. S-Adenosyl-L-methionine tosylate is a dietary supplement with potent antidepressant effects that has been studied for pain relief and has been studied in liver disease and osteoarthritis.

Physicochemical Properties

Molecular Formula	C22H30N6O8S2
Molecular Weight	570.64
Exact Mass	570.156
CAS #	52248-03-0
Related CAS #	S-Adenosyl-DL-methionine;17176-17-9;S-Adenosyl-L-methionine disulfate tosylate;97540-22-2;S-Adenosyl-L-methionine iodide;3493-13-8;S-Adenosyl-L-methionine;29908-03-0;S-Adenosyl-L-methionine (1,4-butanedisulfonate);200393-05-1
PubChem CID	10153079
Appearance	White to yellow solid powder
LogP	1.339
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	7
Heavy Atom Count	38
Complexity	726
Defined Atom Stereocenter Count	5
SMILES	C[S+](CC[C@@H](C(=O)[O-])N)C[C@@H]1[C@H]([C@H]([C@H](N2C=NC3=C(N)N=CN=C32)O1)O)O.CC1=CC=C(C=C1)S(=O)(=O)O
InChi Key	VHPOFDUCFKOUHV-XKGORWRGSA-N
InChi Code	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
Chemical Name	[(3S)-3-amino-3-carboxypropyl]-[[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl]-methylsulfanium;4-methylbenzenesulfonate
Synonyms	52248-03-0; AdoMet; DTXSID40436187; RefChem:553108; DTXCID70387012; ((3S)-3-amino-3-carboxypropyl)-(((2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl)methyl)-methylsulfanium; (2S)-4-(((2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl)methyl-methylsulfonio)-2-azaniumylbutanoate; 5'-[[(3S)-3-Amino-3-carboxypropyl]methylsulfonio]-5'-deoxy-Adenosine tosylate;
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 Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	Endogenous Metabolite - Methyltransferases (including DNA methyltransferases and histone methyltransferases) as a methyl group donor - Methionine adenosyltransferases (MAT) encoded by MAT1A and MAT2A - Glycine N-methyltransferase (GNMT)
ln Vitro	- In hepatocyte models, SAMe regulates methyl group transfer reactions, supporting transmethylation of DNA, proteins, and phospholipids. It enhances glutathione synthesis and reduces oxidative stress markers . Ademetonine, also known as S-Adenosyl-L-methionine tosylate, is involved in three primary metabolic pathways: 1) methylation, which is the body's primary source of methyl groups; 2) transsulfuration, in which Ademetonine forms S-Adenosylhomocysteine (SAH), which is subsequently transformed into homocysteine (Hcy), which can be transformed into cystathionine, and finally into cysteine and sulfate (SO4) to supply additional metabolic intermediates; and 3) Aminopropylation, as Ademetonine is crucial to the synthesis of polyamines, which in turn forms and recycles methionine [2]. Studies conducted in vitro with human articular chondrocytes have demonstrated increases in rabbit proteoglycan production and proliferation rates driven by S-Adenosyl-L-methionine [2].
ln Vivo	- In patients with depression, SAMe (200–1600 mg/day, oral or parenteral) significantly reduces depressive symptoms, with efficacy comparable to tricyclic antidepressants and a faster onset of action . - In a double-blind crossover trial for osteoarthritis, SAMe showed comparable efficacy to celecoxib in relieving pain and improving joint function, as assessed by validated clinical scales . - In MAT1A knockout mice, SAMe supplementation mitigates hepatic oxidative stress, steatohepatitis, and reduces the incidence of hepatocellular carcinoma (HCC) . - In GNMT knockout mice, excessive hepatic SAMe levels induce liver injury, fibrosis, and HCC, which can be partially reversed by dietary methionine restriction . Hepatic S-Adenosyl-L-methionine levels are decreased in mice lacking methionine adenosyltransferase 1a (Mat1a), and they also experience oxidative stress, steatohepatitis, and hepatocellular carcinoma (HCC). On the other hand, persistently elevated liver S-Adenosyl-L-methionine levels may potentially result in damage and HCC. Therefore, to preserve liver health and guard against harm and HCC, appropriate hepatic S-Adenosyl-L-methionine levels are required [3].
Enzyme Assay	- Methyltransferase activity assay: Recombinant methyltransferases are incubated with SAMe and substrate molecules. Methylation efficiency is quantified by measuring S-adenosylhomocysteine (SAH) production or radiolabeled methyl group incorporation . - MAT activity assay: Hepatocyte lysates are incubated with methionine and ATP in the presence of SAMe, and enzyme activity is determined by measuring SAMe synthesis .
Cell Assay	- Hepatocyte culture: Isolated hepatocytes are treated with SAMe to assess changes in glutathione levels, oxidative stress markers (e.g., ROS, lipid peroxides), and gene expression related to methyl metabolism .
Animal Protocol	- MAT1A knockout mouse model: Mice are administered SAMe via oral gavage or intraperitoneal injection at varying doses for 4–12 weeks. Hepatic tissue is collected to evaluate histopathology, oxidative stress, and gene expression . - GNMT knockout mouse model: Mice receive SAMe supplementation in drinking water or diet. Liver triglyceride levels, mitochondrial function, and citric acid cycle flux are measured after 8–16 weeks .
ADME/Pharmacokinetics	- Absorption: Oral bioavailability of SAMe is low due to extensive first-pass metabolism in the liver . - Distribution: Concentrates in the liver, where ~85% of transmethylation reactions occur . - Metabolism: Converted to SAH by methyltransferases, further metabolized to homocysteine .
Toxicity/Toxicokinetics	Effects During Pregnancy and Lactation ◉ Summary of Use during Lactation SAM-e (S-adenosylmethionine) is a naturally occurring methyl radical donor involved in enzymatic transmethylation reactions in humans and animals. SAM-e has no specific lactation-related uses, but it has been used therapeutically for treating postpartum depression, cholestatic jaundice, osteoarthritis and numerous other conditions. SAM-e has poor oral bioavailability. SAM-e is generally well tolerated in adults. The most frequent adverse effects reported are gastrointestinal, such as nausea. Skin rashes have also been reported. No information is available on the clinical use of SAM-e during breastfeeding. However, use of SAM-e by a nursing mother would not be expected to cause any adverse effects in breastfed infants, especially if the infant is older than 2 months. Dietary supplements do not require extensive pre-marketing approval from the U.S. Food and Drug Administration. Manufacturers are responsible to ensure the safety, but do not need to prove the safety and effectiveness of dietary supplements before they are marketed. Dietary supplements may contain multiple ingredients, and differences are often found between labeled and actual ingredients or their amounts. A manufacturer may contract with an independent organization to verify the quality of a product or its ingredients, but that does not certify the safety or effectiveness of a product. Because of the above issues, clinical testing results on one product may not be applicable to other products. More detailed information about dietary supplements is available elsewhere on the LactMed Web site. ◉ Effects in Breastfed Infants Relevant published information was not found as of the revision date. ◉ Effects on Lactation and Breastmilk Relevant published information was not found as of the revision date. - Chronic excessive SAMe levels (e.g., in GNMT deficiency) cause liver injury, fibrosis, and HCC . - In clinical trials, SAMe is well-tolerated with rare adverse effects; manic episodes reported in bipolar patients . - No significant hepatotoxicity observed at therapeutic doses in humans .
References	[1]. S-adenosyl-l-methionine (SAMe) as antidepressant: meta-analysis of clinical studies. Acta Neurol Scand Suppl. 1994;154:7-14. [2]. 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. [3]. S-adenosylmethionine in liver health, injury, and cancer. Physiol Rev. 2012 Oct;92(4):1515-42.
Additional Infomation	- Mechanism: Acts as the primary biological methyl donor, regulating epigenetic modifications, redox balance, and neurotransmitter synthesis (e.g., serotonin, dopamine) . - Clinical Uses: Approved in Europe for depression, osteoarthritis, and cholestasis; used as a dietary supplement in the U.S. . - Liver Health: Critical for maintaining hepatic methyl balance; deficiency linked to liver disease progression . Physiologic methyl radical donor involved in enzymatic transmethylation reactions and present in all living organisms. It possesses anti-inflammatory activity and has been used in treatment of chronic liver disease. (From Merck, 11th ed)

Solubility Data

Solubility (In Vitro)	H2O: 150 mg/mL (262.86 mM)
Solubility (In Vivo)	Solubility in Formulation 1: 100 mg/mL (175.24 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	1.7524 mL	8.7621 mL	17.5242 mL
	5 mM	0.3505 mL	1.7524 mL	3.5048 mL
	10 mM	0.1752 mL	0.8762 mL	1.7524 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.