S-(5'-Adenosyl)-L-methionine iodide (S-Adenosyl-L-methionine iodide) is an important methyl donor present in all organisms.

Physicochemical Properties

Molecular Formula	C15H23IN6O5S
Molecular Weight	526.35
Exact Mass	526.05
CAS #	3493-13-8
Related CAS #	S-Adenosyl-L-methionine tosylate;52248-03-0;S-Adenosyl-L-methionine;29908-03-0
PubChem CID	10143006
Appearance	White to off-white solid powder
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	7
Heavy Atom Count	28
Complexity	533
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.I
InChi Key	XQMWYLXPEGFCFT-XKGORWRGSA-N
InChi Code	InChI=1S/C15H22N6O5S.HI/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;/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25);1H/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;iodide
Synonyms	EINECS 222-486-5; S-(5'-Deoxy-5'-adenosyl)methionine iodide; RefChem:884153; 222-486-5; 3493-13-8; AKOS024284735; ST078876; 2-amino-6-[5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]-5-methyl-5-thiahexa noic acid, iodide
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)

Biological Activity

Targets	Endogenous Metabolite
ln Vitro	1. Analytical Method Development: - A reversed-phase HPLC method was established using a C18 column (250×4.6 mm, 5 μm) with UV detection at 254 nm. The mobile phase was 0.1 M potassium dihydrogen phosphate (pH 3.5)-methanol (90:10, v/v), enabling simultaneous quantification of S-Adenosyl-L-methionine iodide (SAMe iodide) and S-adenosyl-L-homocysteine (SAH) in mouse liver. Detection limits were 0.15 μmol/g (SAMe iodide) and 0.20 μmol/g (SAH). Recovery rates were 92.1±3.8% (SAMe iodide) and 90.5±4.2% (SAH), with intra- and inter-day precision RSD <5% [1] 2. Effect of Methionine Supplementation: - Oral administration of methionine (200 mg/kg) to mice significantly increased hepatic SAMe iodide concentrations from baseline (3.2±0.3 μmol/g) to 5.8±0.4 μmol/g within 2 hours, without altering SAH levels. The SAMe/SAH ratio remained unchanged (1.8±0.2 vs. 1.7±0.1), indicating methionine primarily enhances SAMe iodide synthesis rather than inhibiting SAH hydrolysis [1] According to She et al., the process of perchloric acid extraction results in the conversion of SAM into S-adenosyl-L-homocysteine by donating the methyl group. SAM and (SAH) separation[1].
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.
References	[1]. Reversed-phase high-performance liquid chromatography procedure for the simultaneous determination of S-adenosyl-L-methionine and S-adenosyl-L-homocysteine in mouse liver and the effect of methionine on their concentrations. J Chromatogr B Biomed Sci Appl. 2001 Oct 5;762(1):59-65.
Additional Infomation	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)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	1.8999 mL	9.4994 mL	18.9988 mL
	5 mM	0.3800 mL	1.8999 mL	3.7998 mL
	10 mM	0.1900 mL	0.9499 mL	1.8999 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.