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Thiazolium,3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-5-(2-hydroxyethyl)-4-methyl-chloride (1:1), hydrochloride (1:1)(CAS No. 67-03-8)

Thiazolium,3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-5-(2-hydroxyethyl)-4-methyl-chloride (1:1), hydrochloride (1:1) C12H17ClN4OS.HCl (cas 67-03-8) Molecular Structure

67-03-8 Structure

Identification and Related Records

【Name】
Thiazolium,3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-5-(2-hydroxyethyl)-4-methyl-chloride (1:1), hydrochloride (1:1)
【CAS Registry number】
67-03-8
【Synonyms】
Thiamine,monohydrochloride (8CI)
Thiazolium,3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-5-(2-hydroxyethyl)-4-methyl-chloride, monohydrochloride (9CI)
Thiamol
Thiavit
Tiamidon
Vetalin S
Vitaneuron
3-(4-Amino-2-methylpyrimidyl-5-methyl)-4-methyl-5,b-hydroxyethylthiazolium chloride hydrochloride
Aneurine hydrochloride
Apate drops
Beatine
Bedome
Benerva
Bequin
Berin
Bethiazine
Beuion
Bewon
Biuno
Bivita
Clotiamina
Eskaphen
Lixa-Beta
Slowten
Thiamindichloride
Thiaminal
Thiamine chloride
Thiaminechloride hydrochloride
Thiamine dichloride
Thiaminiumchloride
Thiaminium chloride hydrochloride
Vitamin B1 Hcl
【EINECS(EC#)】
200-641-8
【Molecular Formula】
C12H17ClN4OS.HCl (Products with the same molecular formula)
【Molecular Weight】
337.27
【Inchi】
InChI=1/C12H17N4OS.2ClH/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);2*1H/q+1;;/p-1
【Canonical SMILES】
CC1=C(SC=[N+]1CC2=CN=C(N=C2N)C)CCO.Cl.[Cl-]
【MOL File】
67-03-8.mol

Chemical and Physical Properties

【Appearance】
white crystal powder
【Density】
1.401 g/cm3
【Melting Point】
246-254℃
【Flash Point】
100 C
【Water】
1 g/mL
【Solubilities】
100 g/100 ml
【Color/Form】
Crystals from water
【Stability】
Stable. Combustible. Incompatible with strong oxidizing agents, strong reducing agents.
【Storage temp】
2-8°C
【Computed Properties】
Molecular Weight:337.26852 [g/mol]
Molecular Formula:C12H18Cl2N4OS
H-Bond Donor:3
H-Bond Acceptor:3
Rotatable Bond Count:4
Tautomer Count:3
Exact Mass:336.057837
MonoIsotopic Mass:336.057837
Topological Polar Surface Area:104
Heavy Atom Count:20
Formal Charge:0
Complexity:269
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:3

Safety and Handling

【Hazard Codes】
Xi:Irritant
【Risk Statements】
R36/37/38
【Safety Statements 】
S26;S37/39
【Sensitive】
Light Sensitive & Hygroscopic
【Transport】
25kgs
【Formulations/Preparations】
Bulk Powder, Oral: Tablets: 25 mg, 50 mg, 100 mg, 250 mg, 500 mg. Parenteral Injection: 100 mg/mL. NOTE: Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name.
【Disposal Methods】
SRP: Criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

... /A method for the chemical synthesis of thiamine/ constructs the thiazole ring on a preformed pyrimidine intermediate. Thiamine manufacturers generally follow this approach. Some use malonitrile as the starting material for construction of the 4-amino-5-aminomethyl-2-methylpyrimidine ring (also called Grewe diamine). Others start with acrylonitrile but all proceed via the key Grewe diamine intermediate through to thiothiamine.
... /A method for the chemical synthesis of thiamine consists of separate syntheses of 4-amino-5-bromomethyl-2-methylpyrimidine hydrobromide and of the thiazole moiety or its acetate. Condensation of the two intermediate heterocycles gives thiamine bromide hydrobromide which is converted to thiamine chloride hydrochloride by treatment with silver chloride in methanol or with an ion-exchange resin.
Reaction of 5-(beta-hydroxyethyl)-4-methylthiazole with 2-methyl-4-amino-5-bromomethylpyrimidine, hydrogen bromide salt, followed by neutralization and reaction with hydrochloric acid
U.S. Exports

(1972) 1.34 X 10+7 g
(1975) 5.78 X 10+6 g
(1984) 3.36 X 10+7 g
U.S. Imports

(1972) 1.09 X 10+8 g
(1975) 1.60 X 10+8 g (Vitamin B1)
(1984) 2.80X10+8 g /Vitamin B1, Thiamine hydrochloride or Thiamine Mononitrate, synthetic/
U.S. Production

(1972) Probably > 4.54 x 10+5 grams
(1975) Probably > 4.54 x 10+5 grams
(1986) No data
Consumption Patterns

100% in prevention and treatment of vitamin B1 deficiency (1975)
【Usage】

Nutritional supplement.

Biomedical Effects and Toxicity

【Therapeutic Uses】
Thiamine is used to prevent and to treat thiamine deficiency syndromes including beriberi, Wernicke's encephalopathy syndrome, delirium, and peripheral neuritis associated with pellagra or neuritis of pregnancy (if associated with severe vomiting).
Although thiamine has not been shown by well-controlled trials to have any therapeutic value, the drug has been used for the management of poor appetite, ulcerative colitis, chronic diarrhea, other GI disorders, and the cerebellar syndrome. Thiamine has also been used orally as an insect repellent, but there is a lack of adequate evidence to establish the efficacy of thiamine for this use.
Low plasma thiamine concentrations have been found in patients with type 1 and type 2 diabetes mellitus. In a small placebo-controlled study, benfotiamine /a related vitamin B1 substance/ 100 mg given four times daily by mouth significantly improved neuropathic pain in patients with diabetic polyneuropathy. /Benfotiamine/
/This study assessed/ the effect of thiamine repletion on thiamine status, functional capacity, and left ventricular ejection fraction (LVEF) in patients with moderate to severe congestive heart failure (CHF) who had received furosemide in doses of 80 mg/d or more for at least 3 months. PATIENTS AND METHODS: Thirty patients were randomized to 1 week of double-blind inpatient therapy with either iv thiamine 200 mg/d or placebo (n = 15 each). All previous drugs were continued. Following discharge, all 30 patients received oral thiamine 200 mg/d as outpatients for 6 weeks. Thiamine status was determined by the erythrocyte thiamine-pyrophosphate effect (TPPE). LVEF was determined by echocardiography. RESULTS: TPPE, diuresis, and LVEF were unchanged with iv placebo. After iv thiamine, TPPE decreased (11.7% +/- 6.5% to 5.4% +/- 3.2%; P < 0.01). LVEF increased (0.28 +/- 0.11 to 0.32 +/- 0.09; P < 0.05), as did diuresis (1,731 +/- 800 mL/d to 2,389 +/- 752 mL/d; P < 0.02), and sodium excretion (84 +/- 52 mEq/d to 116 +/- 83 mEq/d, P < 0.05). In the 27 patients completing the full 7-week intervention, LVEF rose by 22% (0.27 +/- 0.10 to 0.33 +/- 0.11, P < 0.01). CONCLUSIONS: Thiamine repletion can improve left ventricular function and biochemical evidence of thiamine deficiency in some patients with moderate-to-severe CHF who are receiving longterm furosemide therapy. [Shimon I et al; Am J Med 98 (5): 485-90 (1995). Available from, as of March 15, 2010:]
【Biomedical Effects and Toxicity】
Absorption of thiamin occurs mainly in the jejunum. At low concentrations of thiamin, absorption occurs by an active transport system that involves phosphyrylation; at higher concentrations, absorption occurs by passive diffusion. Only a small percentage of a high dose of thiamin is absorbed, and elevated serum values result in active urinary excretion of the vitamin.
Thiamin is transported in blood in both erythrocytes and plasma and is excreted in the urine.
Thiamine is absorbed from the small intestine and is phosphorylated in the intestinal mucosa.
The B vitamins are readily absorbed from the gastrointestinal tract, except in malabsorption syndromes. Thiamine is absorbed mainly in the duodenum.
The fat-soluble vitamins ... are absorbed from the skin, as are the fat-insoluble vitamins thiamine ...
Thiamine is widely distributed into body tissues. Body stores of thiamine have been estimated to be about 30 mg with about a 1 mg daily turnover. About 100-200 ug of thiamine is distributed daily into the milk of nursing women receiving a normal diet.
Only a small percentage of a high dose of thiamin is absorbed, and elevated serum values result in active urinary excretion of the vitamin. After an oral dose of thiamin, peak excretion occurs in about 2 hours, and excretion is nearly complete after 4 hours. A 10-mg oral dose of thiamin was given in water, and the mean serum thiamin peaked at 24 nmol/L (7.2 ug/L) -42 percent above baseline. Within 6 hours the serum thiamin concentration had returned to baseline, 17 nmol/L (5.2 ug/L). Prompt urinary excretion of thiamin was also reported.
The apparent lack of toxicity of supplemental thiamin may be explained by the rapid decline in absorption that occurs at intakes above 5 mg and the rapid urinary excretion of thiamin.

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