Thiamine hydrochloride

Iupac Name：2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethanol;chloride;hydrochloride

CAS No.: 67-03-8

Molecular Weight：337.263

Modify Date.: 2022-11-22 15:45

Introduction: Thiamine Hydrochloride is the hydrochloride salt form of thiamine (vitamin B1), a vitamin essential for aerobic metabolism, cell growth, transmission of nerve impulses and acetylcholine synthesis. Vitamin B1 helps prevent various health problems including heart damage.Thiamine hydrochloride is used to prevent and treat thiamine deficiency states, which may occur as a result of inadequate nutrition or intestinal malabsorption. It is also used for the treatment of Wernicke-Korsakoff syndrome, beriberi and thiamine deficiency related to chronic alcoholism. Thiamine hydrochloride is used as a food additive to add brothy/meaty flavor to gravies or soups. It is used also as a food supplement and flavoring ingredient with a bitter taste. View more+

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1. Names and Identifiers

1.1 Name: Thiamine hydrochloride
1.2 Synonyms: Aneurine hydrochloride EINECS 200-641-8 MFCD00012780 THIAMINE THIAMINE CHLORIDE HYDROCHLORIDE THIAMINE HCL Thiazolium,3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-5-(2-hydroxyethyl)-4-methyl-chloride (1:1), hydrochloride (1:1) TIMTEC-BB SBB001377 VIT B1 VITAMIN B1 HCL VITAMIN B1 HYDROCHLORIDE

1.3 CAS No.: 67-03-8

1.4 CID: 6202

1.5 EINECS(EC#): 200-425-3; 200-641-8

1.6 Molecular Formula: C12H18Cl2N4OS (isomer)

1.7 Inchi: InChI=1S/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

1.8 InChkey: DPJRMOMPQZCRJU-UHFFFAOYSA-M

1.9 Canonical Smiles: CC1=C(SC=[N+]1CC2=CN=C(N=C2N)C)CCO.Cl.[Cl-]

1.10 Isomers Smiles: CC1=C(SC=[N+]1CC2=CN=C(N=C2N)C)CCO.Cl.[Cl-]

2. Properties

2.1 Density: 1.401

2.1 Melting point: 246-254℃

2.1 Refractive index: 1.6000 (estimate)

2.1 Flash Point: 100 C

2.1 Precise Quality: 336.05800

2.1 PSA: 104.15000

2.1 logP: -1.00510

2.1 Solubility: 1 g/mL

2.2 AnalyticLaboratory Methods: AOAC Method 986.27- Fluorometric Method. The thiamine; content of the sample is estimated by oxidizing thiamine; to thiochrome; and measuring fluorescence. Intensity of fluorescence is proportional to thiamine; concentration.

2.3 Appearance: White to almost white Crystalline Powder

2.4 Storage: Hygroscopic. Light Sensitive. Ambient temperatures.

2.5 Chemical Properties: White or almost white, crystalline powder or colourless crystals.

2.6 Color/Form: Crystals from water

2.7 Decomposition: When heated to decomposition it emits very toxic fumes of /nitric oxide;/, /sulfur oxide;/, and /chlorine;/.

2.8 Odor: SLIGHT, CHARACTERISTIC

2.9 PH: 2.7-3.3

2.10 pKa: pKa 4.8 (Uncertain);9.0 (Uncertain)

2.11 Water Solubility: H2O: 0.1?g/mL at?20?°C, clear, colorless

2.12 Stability: Stable. Combustible. Incompatible with strong oxidizing agents, strong reducing agents.

2.13 StorageTemp: room temp

3. Use and Manufacturing

3.1 Definition: ChEBI: A hydrochloride obtained by combining thiamine chloride with one molar equivalent of hydrochloric acid.

3.2 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 179 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 160 of 179 companies. For more detailed information, please visit ECHA C&L website

Of the 7 notification(s) provided by 19 of 179 companies with hazard statement code(s):

H302 (10.53%): Harmful if swallowed [Warning Acute toxicity, oral]
H315 (84.21%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (84.21%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (73.68%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501

3.3 Methods of Manufacturing: Vitamin B1 naturally exists in foods such as rice bran, bran, lean meat, peanuts, etc. Pure products are usually prepared by chemical synthesis.?Excess acetamidine hydrochloride is condensed with α-dimethoxy-β-methoxypropionitrile to 3, 6-dimethyl-1, 2-dihydro-2 in alkaline (methanol and sodium methoxide) medium. 4, 5, 7-tetraazanaphthalene, then hydrolyzed at 98～100℃, then ring-opened under alkaline conditions to generate 2-methyl-4-amino-5-aminomethylpyrimidine; then it reacts with carbon disulfide and ammonia water , And then condensed with acetic acid-γ-chloro-γ-levulinic acid ester, and then hydrolyzed and cyclically synthesized thiothiamine hydrochloride in hydrochloric acid at 75～78℃, and finally neutralized with ammonia water, hydrogen peroxide, Acidification with hydrochloric acid yields thiamine hydrochloride.

3.4 Purification Methods: The hydrochloride crystallises from 95% EtOH (solubility is ca 1%). The monohydrate is dehydrated at 100o in vacuo over H2SO4, but is hygroscopic and picks up one molecule of H2O readily. It can be sterilised at 100o if the pH of the solution is below 5.5. The nitrate has m 196-200o(dec) and is more stable than the hydrochloride. The picrolonate crystallises from H2O and is dimorphic, m 164-165o and 228-229o(dec). [Todd & Bergel J Chem Soc 364, 367 1937, J Am Chem Soc 58 1063, 1504 1936, 59 526 1937, Beilstein 27 IV 1766.] Thiamine hydrochloride Preparation Products And Raw materials Raw materials

3.5 Usage: Thiamine is the water-soluble vitamin b1, required for normal digestion and functioning of nerve tissues and in the prevention of beriberi. It also acts as a coenzyme in the metabolism of carbohydrates. During processing, the higher and longer the heating period, the greater the loss. The loss is reduced in the presence of acid. Thiamine hydrochloride and thiamine mononitrate are two available forms. The mononitrate form is less hygroscopic and more stable than the hydrochloride form, making it suitable for use in beverage powders. It is used in enriched flour and is found as thiamine mononitrite in frozen egg substitute and crackers.

4. Safety and Handling

4.1 Symbol: GHS02, GHS06, GHS08

4.1 Hazard Codes: Xi

4.1 Signal Word: Danger

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S26;S37/39

4.1 Hazard Declaration: H225-H301 + H311 + H331-H370

4.1 DisposalMethods: 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.

4.2 RIDADR: 25kgs

4.2 Safety Profile: Poison by intravenousand intraperitoneal routes. Mildly toxic byingestion. The vitamin is destroyed byalkalies and alkaline drugs such asphenobarbital sodium and by oxidzing andreducing agents. When heated todecomposition it emits very toxic fumes ofHCl, Cl-, SOx, and NOx.

4.3 Caution Statement: P210-P260-P280-P301 + P310-P311

4.3 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.

4.4 WGK Germany: 1

4.4 RTECS: XI7350000

4.4 Sensitive: Light Sensitive & Hygroscopic

4.5 Toxicity: LD50 in mice (mg/kg): 89.2 i.v.; 8224 orally (Winter)

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : in D2O

13C NMR : Predict

1H NMR : 400 MHz in DMSO-d6

7. Synthesis Route

67-03-8Total: 7 Synthesis Route

13051-49-5 20 Suppliers

67-03-8 299 Suppliers

Literatures:
Contant; Forzy; Hengartner; Moine Helvetica Chimica Acta, 1990 , vol. 73, # 5 p. 1300 - 1305
Yield: null

137-00-8 280 Suppliers

73-66-5 5 Suppliers

67-03-8 299 Suppliers

Literatures:
Litvak Pharmaceutical Chemistry Journal, 1999 , vol. 33, # 2 p. 101 - 103
Yield: null

31375-20-9

13051-49-5 20 Suppliers

67-03-8 299 Suppliers

Literatures:
Bergel; Todd Journal of the Chemical Society, 1938 , p. 26 Full Text Show Details Andersag; Westphal Chemische Berichte, 1937 , vol. 70, p. 2035,2044 Full Text Show Details Todd; Bergel Journal of the Chemical Society, 1937 , p. 367 Journal of the Chemical Society, 1938 , p. 28
Yield: null

View all

8. Precursor and Product

precursor:

137-00-8

55289-66-2

64-18-6

13051-49-5

31375-19-6

73-66-5

7732-18-5

31375-20-9

663179-26-8

50596-94-6

24361-62-4

product :

137-00-8

1137181-42-0

154-87-0

10023-48-0

59-43-8

299-88-7

63423-50-7

15743-04-1

59-58-5

532-40-1

28168-40-3

15666-52-1

532-43-4

View all

9. Other Information

9.0 Storage Conditions: Vitamin B1 naturally exists in foods such as rice bran, bran, lean meat, peanuts, etc. Pure products are usually prepared by chemical synthesis.?Excess acetamidine hydrochloride is condensed with α-dimethoxy-β-methoxypropionitrile to 3, 6-dimethyl-1, 2-dihydro-2 in alkaline (methanol and sodium methoxide) medium. 4, 5, 7-tetraazanaphthalene, then hydrolyzed at 98～100℃, then ring-opened under alkaline conditions to generate 2-methyl-4-amino-5-aminomethylpyrimidine; then it reacts with carbon disulfide and ammonia water , And then condensed with acetic acid-γ-chloro-γ-levulinic acid ester, and then hydrolyzed and cyclically synthesized thiothiamine hydrochloride in hydrochloric acid at 75～78℃, and finally neutralized with ammonia water, hydrogen peroxide, Acidification with hydrochloric acid yields thiamine hydrochloride.

9.1 Experimental Properties: Monoclinic plates in rosette-like clusters. Slight thiazole odor; bitter taste; decomposes at 248 °C. One gram dissolves in approximately 1 mL water, 18 mL glycerol, 100 mL 95% alcohol, 315 mL absolute alcohol; more soluble in methanol. Soluble in propylene glycol. Practically insoluble in ether, benzene, hexane, chloroform. pH of 1% wt/vol solution in water 3.13; pH of 0.1% wt/vol solution in water 3.58. On exposure to air of average humidity, the vitamin absorbs an amount of water corresponding to nearly one mole, forming a hydrate.|HYGROSCOPIC; NUT-LIKE ODOR /HYDROCHLORIDE/|READILY SPLIT BY SULFITE INTO ITS PYRIMIDINE & THIAZOLE CONSTITUENTS|Crystals. MP: 196-200 °C, decomposes; practically nonhygroscopic; pKa = 4.9. Solubility in water (g/100 mL): 2.7 (25 °C); approximately 30 (100 °C). pH of 2% aqueous solution 6.5 to 7.1, more stable than the hydrochloride; suitable for enrichment of flours and feeds, multivitamin preparations /Mononitrate/|SMALL WHITE CRYSTALS OR CRYSTALLINE POWDER /HYDROCHLORIDE/|Thiamine hydrochloride in the dry state is stable. Acidic solutions having a pH below 5.5 preferably from 5.0 to 3.5 are also relatively stable. Alkalies destroy it. It is precipitated from solution by several of the alkaloidal reagents such as mercuric chloride, iodine, picric acid, tannin, and Mayer's reagent. It is sensitive to both oxidizing and reducing agents. /Hydrochloride/|For more Other Experimental Properties (Complete) data for Vitamin B1 (6 total), please visit the HSDB record page.

9.2 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.

9.3 Special Reports: NAS, Food and Nutrition Board, Institute of Medicine; Dietary Reference Intakes for Thiamin, Riboflavin, Niacin, Vitamin B6, Folate, Vitamin B12, Pantothenic Acid, Biotin, and Choline. National Academy Press, Washington, D.C. (1998).[Available from, as of March 2, 2010: http://www.nap.edu/catalog/6015.html]

9.4 Interactions: ... High dietary levels of thiamine hydrochloride have been reported to depress the metabolism of zoxazolamine and aminopyrine in rats without significantly altering the oxidative metabolism of hexobarbitone. /Thiamine hydrochloride/|In rats treated with PCB, vitamin B1 levels in blood, liver, and sciatic nerve decreased, transketolase activity decreased, and pyrophosphate effect increased. In DDT-treated rats, vitamin B1 levels decreased in blood, brain, and liver, as did transketolase activity, while pyrophosphate effect increased.|Although the clinical importance is unknown, thiamine reportedly may enhance the effect of neuromuscular blocking agents.|... Alcohol inhibits absorption of thiamine.|For more Interactions (Complete) data for Vitamin B1 (9 total), please visit the HSDB record page.

9.5 Natural Pollution Sources: Vitamin B1 is found in all plants and animals; however, most organisms contain only low concentrations(1,2). It is found intracellularly in microorganisms, in plants (although unevenly distributed), and in tissue of animals, with the highest amounts occurring in the heart, kidney, liver, and brain(1). In plants, vitamin B1 occurs predominantly as free thiamine and in animals it occurs almost entirely in phophorylated forms, mainly thiamine pyrophosphate(2). It is biosynthesized by microorganisms and plants. Dietary sources include whole grains, meat products, vegetables, milk, legumes and fruit. Vitamin B1 is also present in rice husks and yeast(3).

9.6 Food Survey Values: Dietary Sources of Vitamin B1(1). [Table#840]|Whole grain cereals, legumes such as beans and lentils, nuts, lean pork and yeast are rich sources of vitamin B1(1). [Table#841]

9.7 Human Exposure: NIOSH (NOES Survey 1981-1983) has statistically estimated that 18,939 workers (9.502 of these were female) were potentially exposed to vitamin B1 in the US(1).

9.8 Livertox Summary: Vitamin B refers to several water soluble vitamins often found together in foods, all of which are necessary for normal growth and metabolism, but none of which are synthesized in adequate amounts by humans. The common forms of vitamin B include vitamin B1 (thiamine), B2 (riboflavin), B3 (niacin), B6 (pyridoxine) and B12 (cyanocobalamin). Except for niacin (when given in high doses), there is no evidence that the other B vitamins, in physiologic or even super-physiologic high doses cause liver injury or jaundice. The major forms of vitamin B and selected other water soluble vitamins (biotin, pantothenic acid, choline) are discussed briefly in this record.

9.9 Drug Classes: Vitamins

9.10 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.|For more Therapeutic Uses (Complete) data for Vitamin B1 (11 total), please visit the HSDB record page.

9.11 Drug Warnings: Serious hypersensitivity/anaphylactic reactions can occur, especially after repeated administration. Deaths have resulted from IV or IM administration of thiamine.|Anaphylaxis as an adverse systemic reaction to thiamine (vitamin B1) has been described in the literature since 1938. Although its precise mechanism is still uncertain, the reaction appears to involve immediate type hypersensitivity and to be exclusively related to parenteral administration...|Anaphylaxis. There have been occasional reports of serious and even fatal responses to the parenteral administration of thiamin. The clinical characteristics have strongly suggested an anaphylactic reaction. Symptoms associated with thiamin-induced anaphylaxis include anxiety, pruritus, respiratory distress, nausea, abdominal pain, and shock, sometimes progressing to death.|Adverse reactions with thiamine are rare, but hypersensitivity reactions have occurred, mainly after parenteral doses. These reactions have ranged in severity from very mild to, very rarely, fatal anaphylactic shock ... The UK Committee on Safety of Medicines had received, between 1970 and July, 1988, 90 reports of adverse reactions associated with the use of an injection containing high doses of vitamins B and C. The most frequent reactions were anaphylaxis (41 cases, including 2 fatalities), dyspnea or bronchospasm (13 cases), and rash or flushing (22 cases); 78 of the reactions occurred during, or shortly after, intravenous injection and the other 12 after intramuscular injectdion. They recommended that parenteral treatment be used only when essential, and that, when given, facilities for treating anaphylaxis should be available. They also recommended that, when the intravenous route was used, the injection be given slowly (over 10 minutes). Various authors have noted that parenteral treatment is essential for the prophylaxis and treatment of Wernicke's encephalopathy. However, further reports of anaphylaxis to parenteral thiamine have since been described, including one with a fatal outcome.|For more Drug Warnings (Complete) data for Vitamin B1 (15 total), please visit the HSDB record page.

9.12 Absorption: 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.|For more Absorption, Distribution and Excretion (Complete) data for Vitamin B1 (8 total), please visit the HSDB record page.

9.13 Metabolism: Converted in vivo to thiamine diphosphate, a coenzyme in the decarboxylation of alpha-keto acids.|Compound 3-(2'-methyl-4'-amino-5'-pyrimidylmethyl)-4-methylthiazole-5-acetic acid, ie thiamine acetic acid, 2-methyl-4-amino-5-formylaminomethylpyrimidine, and 5-(2-hydroxyethyl)-4-methylthiazole have been identified as important metabolites of thiamine, vitamin B1.|Biotransformation of thiamine in mammals is generally supposed to /yield/ thiochrome, thiamine disulfide, 5-(2-hydroxyethyl)-4-methyl-thiazole, and some form corresponding to pyrimidine residue of thiamine.|Thiamine is metabolized in the liver of animals. Several urinary metabolites of thiamine have been identified in humans. Little or no unchanged thiamine is excreted in urine following administration of physiologic doses; however, following administration of larger doses, both unchanged thiamine and metabolites are excreted after tissue stores become saturated.

9.14 Biological Half Life: The biological half-life of the vitamin is in the range of 9-18 days.|With higher pharmacological levels, namely repetitive 250-mg amounts taken orally and 500 mg given intramuscularly, nearly 1 week was required for steady state plasma concentrations to be reached; a mean elimination half-life of 1.8 days was estimated.|Total thiamin content of the adult human has been estimated to be approximately 30 mg, and the biological half-life of the vitamin is probably in the range of 9 to 18 days.

9.15 Antidote: /SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

9.16 Human Toxicity Excerpts: /SIGNS AND SYMPTOMS/ Adverse reactions with thiamine are rare, but hypersensitivity reactions have occurred, mainly after parenteral doses. These reactions have ranged in severity from very mild to, very rarely, fatal anaphylactic shock ... The UK Committee on Safety of Medicines had received, between 1970 and July, 1988, 90 reports of adverse reactions associated with the use of an injection containing high doses of vitamins B and C. The most frequent reactions were anaphylaxis (41 cases, including 2 fatalities), dyspnea or bronchospasm (13 cases), and rash or flushing (22 cases); 78 of the reactions occurred during, or shortly after, intravenous injection and the other 12 after intramuscular injection.|/SIGNS AND SYMPTOMS/ Serious hypersensitivity/anaphylactic reactions can occur, especially after repeated administration. Deaths have resulted from IV or IM administration of thiamine.|/SIGNS AND SYMPTOMS/ Anaphylaxis. There have been occasional reports of serious and even fatal responses to the parenteral administration of thiamin. The clinical characteristics have strongly suggested an anaphylactic reaction. Symptoms associated with thiamin-induced anaphylaxis include anxiety, pruritus, respiratory distress, nausea, abdominal pain, and shock, sometimes progressing to death.|/SIGNS AND SYMPTOMS/ Allergic Sensitivity and Pruritus. One case of pruritus after an intake of 500 mg/day of thiamin intramuscularly /was reported/. Another study, which involved intravenous administration of 100 mg of thiamin hydrochloride to 989 patients, reported a burning effect at the injection site in 11 patients and pruritus in 1 patient. No reports of pruritus after thiamin ingestion were found.|For more Human Toxicity Excerpts (Complete) data for Vitamin B1 (13 total), please visit the HSDB record page.

9.17 Mesh Entry Terms: thiamine chloride hydrochloride

9.18 Production: (1972) Probably > 4.54 x 10+5 grams|(1975) Probably > 4.54 x 10+5 grams|(1986) No data

9.19 Consumption Patterns: 100% in prevention and treatment of vitamin B1 deficiency (1975)

9.20 Formulations: 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.

9.21 Manufacturing Info: Thiazolium, 3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-5-(2-hydroxyethyl)-4-methyl-, chloride, hydrochloride (1:1:1): ACTIVE|Most of the thiamine commercialy available is synthetic|Biosynthesized by microorganisms and plants. Dietary sources include whole grains, meat products, vegetables, milk, legumes and fruit. Also present in rice husks and yeast.

9.22 Use Classification: Food additives -> Flavoring Agents|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Flavoring Agents -> JECFA Flavorings Index|Cosmetics -> Skin conditioning

9.23 Merck: 14,9295

9.24 BRN: 3851771

9.25 Description: Thiamine Hydrochloride is the hydrochloride salt form of thiamine (vitamin B1), a vitamin essential for aerobic metabolism, cell growth, transmission of nerve impulses and acetylcholine synthesis. Vitamin B1 helps prevent various health problems including heart damage.
Thiamine hydrochloride is used to prevent and treat thiamine deficiency states, which may occur as a result of inadequate nutrition or intestinal malabsorption. It is also used for the treatment of Wernicke-Korsakoff syndrome, beriberi and thiamine deficiency related to chronic alcoholism. Thiamine hydrochloride is used as a food additive to add brothy/meaty flavor to gravies or soups. It is used also as a food supplement and flavoring ingredient with a bitter taste.

9.26 References: [1] https://www.drugs.com
[2] Shmuel Yannai (2012) Dictionary of Food Compounds with CD-ROM, Second Edition
[3] https://www.medicines.org.uk

9.27 Chemical Properties: White or almost white, crystalline powder or colourless crystals.

9.28 Uses: Thiamine is the water-soluble vitamin b1, required for normal digestion and functioning of nerve tissues and in the prevention of beriberi. It also acts as a coenzyme in the metabolism of carbohydrates. During processing, the higher and longer the heating period, the greater the loss. The loss is reduced in the presence of acid. Thiamine hydrochloride and thiamine mononitrate are two available forms. The mononitrate form is less hygroscopic and more stable than the hydrochloride form, making it suitable for use in beverage powders. It is used in enriched flour and is found as thiamine mononitrite in frozen egg substitute and crackers.

9.29 Uses: Thiamine is a essential nutrient required for carbohydrate metabolism; also involved in nerve function. Biosynthesized by microorganisms and plants. Dietary sources include whole grains, meat products , vegetables, milk, legumes and fruit. Also present in rice husks and yeast. Converted in vivo to Thiamine diphosphate, a coenzyme in the decarboxylation of α-keto acids. Chronic deficiency may lead t o neurological impairment, bariberi, Wernicke-Korsakoff syndrome.

9.30 Uses: A cofactor required for oxidation of carbohydrates and for the synthesis of ribose.

9.31 Definition: ChEBI: A hydrochloride obtained by combining thiamine chloride with one molar equivalent of hydrochloric acid.

9.32 Safety Profile: Poison by intravenous and intraperitoneal routes. Mildly toxic by ingestion. The vitamin is destroyed by alkalies and alkaline drugs such as phenobarbital sodium and by oxidzing and reducing agents. When heated to decomposition it emits very toxic fumes of HCl, Cl-, SOx, and NOx.

9.33 Purification Methods: The hydrochloride crystallises from 95% EtOH (solubility is ca 1%). The monohydrate is dehydrated at 100o in vacuo over H2SO4, but is hygroscopic and picks up one molecule of H2O readily. It can be sterilised at 100o if the pH of the solution is below 5.5. The nitrate has m 196-200o(dec) and is more stable than the hydrochloride. The picrolonate crystallises from H2O and is dimorphic, m 164-165o and 228-229o(dec). [Todd & Bergel J Chem Soc 364, 367 1937, J Am Chem Soc 58 1063, 1504 1936, 59 526 1937, Beilstein 27 IV 1766.]

9.34 Description: In 1912, Cashmir Funk isolated thiamine from rice husks and coined the term ‘vitamine’ because it was required for life (‘vita’) and because thiamine contained nitrogen (‘amine’). Thiamine, formerly known as B1, is water soluble. Thiamine is a vital cofactor for enzymes and coenzymes of glycolysis, the Kreb’s cycle, the pentose phosphate pathway. Thiamine is also involved in the biosynthesis of the neurotransmitters acetylcholine and gamma-aminobutyric acid and in nerve propagation.

9.35 Chemical Properties: Vitamin B1 has an odor slightly reminiscent of thiazole and a bitter taste. When exposed to air, the vitamin rapidly absorbs about 4% of water.

9.36 Occurrence: Rice husks are reportedly the principal source of vitamin B1; in variable amounts it is a constituent of yeast, milk, green leaves, roots and tubers; it is also present in high concentration in seeds, and in lesser amount in different animal organs and muscles.

9.37 Preparation: By linking the preformed thiazole and pyrimidine ring system.

9.38 General Description: Thiamine is a water-soluble vitamin of the B complex whose phosphate derivatives are involved in many cellular processes required for overall human health. Thiamine deficiency, often the result of impaired nutritional status associated with chronic diseases from alcoholism to HIV-AIDS, is monitored in patient whole blood samples by HPLC.

9.39 Usage: Thiamine hydrochloride plays an important role as a nutrient for carbohydrate metabolism and in nerve function. It finds application as a food-additive to add a brothy/meaty flavor to gravies or soups. It is involved in the preparation of 3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-5-(2-hydroxy-ethyl)-4-methyl-thiazolium chloride. In addition, it finds use in amino acid synthesis in cultured cells, which is present in many classical and serum-free formulations.

10. Computational chemical data

Molecular Weight: 337.263g/mol
Molecular Formula: C₁₂H₁₈Cl₂N₄OS
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 336.0578378
Monoisotopic Mass: 336.0578378
Complexity: 269
Rotatable Bond Count: 4
Hydrogen Bond Donor Count: 3
Hydrogen Bond Acceptor Count: 6
Topological Polar Surface Area: 104
Heavy Atom Count: 20
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 3
CACTVS Substructure Key Fingerprint: AAADceBzoABGAAAAAAAAAAAAAAAAAWAAAAAsAAAAAAAAAAAB4AAAHgQQCAAADAjh3wavsZdMEgikAxZnZACA8KlxCLgBWDQ4RBiAOIJgyUAERAgsQAPISCKgAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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