3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium

• ChemBase ID: 38
• Molecular Formular: C12H17N4OS+
• Molecular Mass: 265.35458
• Monoisotopic Mass: 265.11230718
• SMILES: s1c(c([n+](Cc2c(nc(nc2)C)N)c1)C)CCO
• Canonical SMILES: OCCc1sc[n+](c1C)Cc1cnc(nc1N)C
• InChI: InChI=1S/C12H17N4OS/c1-8-11(3-4-17)18-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7,17H,3-4,6H2,1-2H3,(H2,13,14,15)/q+1
• InChIKey: JZRWCGZRTZMZEH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium
• IUPAC Traditional name: thiamine
• Brand Name: Aneurin; Antiberiberi Factor; Betalin S; Betaxin; Bewon; Biamine; Cernevit-12; Infuvite Pediatric; M.V.I.-12 Lyophilized; Vitaped; Vitaneuron
• Synonyms: Thiamine Hcl; Thiamin; Vitamin B1; Thiadoxine; Thiamine

Database IDs

• CAS Number: 59-43-8
• PubChem SID: 160963501; 46507321
• PubChem CID: 1130

CALCULATED PROPERTIES

JChem

• Acid pKa: 15.504604
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -3.4096768
• LogD (pH = 7.4): -3.1032324
• Log P: -3.0974126
• Molar Refractivity: 73.3997 cm^3
• Polarizability: 26.833982 Å^3
• Polar Surface Area: 75.91 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.11
• LOG S: -4.29
• Solubility (Water): 1.53e-02 g/l

PROPERTIES

Physical Property

• Solubility: 500 mg/mL [MERCK INDEX (1996); approx.]
• Hydrophobicity(logP): -3.93 (HCl salt)

DETAILS

DrugBank - DB00152

• Drug Groups: approved; nutraceutical
• Description: Thiamine or thiamin, also known as vitamin B1, is a colorless compound with the chemical formula C12H17N4OS. It is soluble in water and insoluble in alcohol. Thiamine decomposes if heated. Thiamine was first discovered by Umetaro Suzuki in Japan when researching how rice bran cured patients of Beriberi. Thiamine plays a key role in intracellular glucose metabolism and it is thought that thiamine inhibits the effect of glucose and insulin on arterial smooth muscle cell proliferation. Thiamine plays an important role in helping the body convert carbohydrates and fat into energy. It is essential for normal growth and development and helps to maintain proper functioning of the heart and the nervous and digestive systems. Thiamine cannot be stored in the body; however, once absorbed, the vitamin is concentrated in muscle tissue.
• Indication: For the treatment of thiamine and niacin deficiency states, Korsakov's alcoholic psychosis, Wernicke-Korsakov syndrome, delirium, and peripheral neuritis.
• Pharmacology: Thiamine is a vitamin with antioxidant, erythropoietic, cognition-and mood-modulatory, antiatherosclerotic, putative ergogenic, and detoxification activities. Thiamine has been found to protect against lead-induced lipid peroxidation in rat liver and kidney. Thiamine deficiency results in selective neuronal death in animal models. The neuronal death is associated with increased free radical production, suggesting that oxidative stress may play an important early role in brain damage associated with thiamine deficiency. Thiamine plays a key role in intracellular glucose metabolism and it is thought that thiamine inhibits the effect of glucose and insulin on arterial smooth muscle cell proliferation. Inhibition of endothelial cell proliferation may also promote atherosclerosis. Endothelial cells in culture have been found to have a decreased proliferative rate and delayed migration in response to hyperglycemic conditions. Thiamine has been shown to inhibit this effect of glucose on endothelial cells.
• Toxicity: Thiamine toxicity is uncommon; as excesses are readily excreted, although long-term supplementation of amounts larger than 3 gram have been known to cause toxicity. Oral mouse LD₅₀ = 8224 mg/kg, oral rat LD₅₀ = 3710 mg/kg.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Absorbed mainly from duodenum, by both active and passive processes
• Protein Binding: 90-94%
• References: Slater PV: Multi-level preparation for nursing impact on nursing practice. Aust Nurses J. 1978 Jun;7(11):40-3. [Pubmed] ; Kopriva V, Bilkovic R, Licko T: [Tumours of the small intestine (author's transl)] Cesk Gastroenterol Vyz. 1977 Dec;31(8):549-53. [Pubmed] ; Beissel J: [The role of right catheterization in valvular prosthesis surveillance (author's transl)] Ann Cardiol Angeiol (Paris). 1977 Dec;26(6):587-9. [Pubmed] ; Lonsdale D, Shamberger RJ, Audhya T: Treatment of autism spectrum children with thiamine tetrahydrofurfuryl disulfide: a pilot study. Neuro Endocrinol Lett. 2002 Aug;23(4):303-8. [Pubmed] ; Lonsdale D: A review of the biochemistry, metabolism and clinical benefits of thiamin(e) and its derivatives. Evid Based Complement Alternat Med. 2006 Mar;3(1):49-59. [Pubmed]
• External Links: Wikipedia; Drugs.com

REFERENCES

• Slater PV: Multi-level preparation for nursing impact on nursing practice. Aust Nurses J. 1978 Jun;7(11):40-3. Pubmed
• Kopriva V, Bilkovic R, Licko T: [Tumours of the small intestine (author's transl)] Cesk Gastroenterol Vyz. 1977 Dec;31(8):549-53. Pubmed
• Beissel J: [The role of right catheterization in valvular prosthesis surveillance (author's transl)] Ann Cardiol Angeiol (Paris). 1977 Dec;26(6):587-9. Pubmed
• Lonsdale D, Shamberger RJ, Audhya T: Treatment of autism spectrum children with thiamine tetrahydrofurfuryl disulfide: a pilot study. Neuro Endocrinol Lett. 2002 Aug;23(4):303-8. Pubmed
• Lonsdale D: A review of the biochemistry, metabolism and clinical benefits of thiamin(e) and its derivatives. Evid Based Complement Alternat Med. 2006 Mar;3(1):49-59. Pubmed