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Thiamine

HCID 1130
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Basic information

CAS
59-43-8
Standard SMILES
Cc1ncc(C[n+]2csc(CCO)c2C)c(N)n1
InChIKey
JZRWCGZRTZMZEH-UHFFFAOYSA-N
Molecular formula
C12H17N4OS+
Average molar mass
265.36 g/mol
Monoisotopic mass
265.11230735

Overview

Thiamine(1+) is a primary alcohol that is 1,3-thiazol-3-ium substituted by (4-amino-2-methylpyrimidin-5-yl)methyl, methyl and 2-hydroxyethyl groups at positions 3, 4 and 5, respectively. It has a role as a mouse metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a human metabolite. It is a primary alcohol and a vitamin B1. It is a conjugate base of a thiamine(2+).

Names & identifiers

Preferred name
Thiamine
IUPAC
2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethanol
English name
Thiamine hydrochloride
Molecular formula
C12H17N4OS+
Molecular weight
265.35

Names & synonyms

thiaminethiaminvitamin B1AneurinAntiberiberi factorBetaxinthiaminiumBewonthiamine(1+) ionBetabionThiaminalTrophite
Show more names
THIAMINE HCLVITAMIN B1 HCLVIT B1FEMA 3322Thiamine ionTHIAMIN HYDROCHLORIDEANEURIN HCLANEURINE HCL
VinothiamLixa-betaVetalin S3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-iumVitamin B 1OryzanineThiamine, chlorideB-Amin

Database identifiers

CAS
59-43-8、70-16-6
PubChem CID
1130
DTXSID
DTXSID50220251
ChEMBL
CHEMBL1588
ChEBI
CHEBI:18385
UNII
4ABT0J945J
EC Number
200-425-3

Properties

Computed structural properties

XLogP
1
Topological polar surface area
104 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
5
Rotatable bonds
4
Heavy atoms
18
Formal charge
1
Complexity
268

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Vitamins and Derivatives
Drugs · 2 items

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals

OdorSLIGHT, CHARACTERISTIC
Food AdditivesFLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT, NUTRIENT SUPPLEMENT -> FDA Substance added to food
Color/FormCrystals from water
Solubility · 5 items

SLIGHTLY SOL IN ALC & CHLOROFORM /MONONITRATE/

MONONITRATE IS MUCH LESS SOL IN WATER THAN HYDROCHLORIDE

In water, approximately 5.0X10+5 mg/L, temp not specified

500.0 mg/mL

Soluble in water, propylene glycol; Insoluble in ether, benzene, hexane, chloroform

Dietary IngredientsThiamin
Human Drugs · 3 items

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Vitamins and minerals

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 3 items

This chemical does not meet GHS hazard criteria for 100% (6 of 6) of all reports.

Not Classified

Aggregated GHS information provided per 6 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 2 items

Chemical: Thiazolium, 3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-5-(2-hydroxyethyl)-4-methyl-, chloride (1:1)

Thiamine: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards Summary · 1 item

A water-soluble vitamin used to treat beriberi and Wernicke-Korsakoff syndrome; Anaphylactoid reactions were reported after intravenous injection--rare with new preparations; [Olson, p. 628] Hydrochloride: Safe when used as a flavoring agent in food; [JECFA] Occupational asthma confirmed with broncho-provocation testing in a worker manufacturing cereal; [Malo]

Special Reports · 1 item

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]

Hazard Classes and CategoriesNot Classified

Safety & protection

Chemistry & industry

Pharmacology

ATC Code · 3 items

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

A11DA01

Bionecessity · 5 items

Persons who may have increased needs for thiamin include those being treated with hemodialysis or peritoneal dialysis, individuals with malabsorption syndrome, women carrying more than one fetus, and lactating women who are nursing more than one infant.

Heavy exercise under certain conditions may increase the requirement for thiamin as well as other vitamins, but the observations on the effects of physical activity on the thiamin requirement have been inconsistent, the effects small, and the experimental conditions highly variable. ... Under normal conditions, physical activity does not appear to influence thiamin requirements to a substantial degree. However, those who are engaged in physically demanding occupations or who spend much time training for active sports may require additional thiamin.

It has been observed that during periods of starvation such as in war, larger individuals present signs of beriberi more rapidly than do those with smaller body builds, indicating their greater needs for thiamin and other energy-related nutrients.

Thiamin ... functions as a coenzyme in the metabolism of carbohydrates and branched-chain amino acids ... The adult requirements for thiamin are based on the amount of the vitamin needed to achieve and maintain normal erythrocyte transketolase activity, while avoiding excessive thiamin excretion ... Dietary Reference Intakes (DRIs) are listed by life stage group in the table.

For more Bionecessity (Complete) data for Vitamin B1 (43 total), please visit the HSDB record page.

Protein Binding90-94%
Pharmacodynamics · 1 item

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.

Related reactions

30 records
New reaction record
HRID 29741 reaction equation
HRID 29741As reactantuspto-grants-2008_09
HRID 399376 reaction equation
HRID 399376As reactantuspto-grants-1998_10
HRID 399377 reaction equation
HRID 399377As reactantuspto-grants-1998_10
HRID 414883 reaction equation
HRID 414883As reactantuspto-grants-2012_01
HRID 500295 reaction equation
HRID 500295As reactantuspto-grants-2010_08
HRID 584767 reaction equation
HRID 584767As reactantuspto-grants-2005_08
HRID 584768 reaction equation
HRID 584768As reactantuspto-grants-2005_08
HRID 967694 reaction equation
HRID 967694As reactantuspto-grants-2005_10
Page 1 of 4

Compound notes

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Nikkaji
J209.352I
Decomposition
When heated to decomposition it emits very toxic fumes of /nitric oxide/, /sulfur oxide/, and /chlorine/.
Melting Point · 3 items

164 °C

MP: 248 °C, DECOMP /HYDROCHLORIDE/

248 °C

Physical Description · 3 items

Solid with a slight odor; [HSDB] Crystals; [Avocado Research MSDS]

Solid

Small white to yellowish crystals or crystalline powder; slight characteristic odour reminescent of thiazole

Stability/Shelf Life · 5 items

Stable under normal storage conditions; it is degraded in neutral and alkaline solutions (even at room temp)

Mononitrate is less hygroscopic and hence is more stable than the hydrochloride /Mononitrate and hydrochloride salts/

Stability is excellent in low pH fruit drinks, eg, losses in drinks are 6% after 12 mo at room temp

Stability in frozen drink concentrate is excellent

For more Stability/Shelf Life (Complete) data for Vitamin B1 (9 total), please visit the HSDB record page.

Physicochemical properties

Melting point
250 °C · 250 °C (dec.)(lit.)
storage temp.
2 · 2-8°C
solubility
2 O: · H2O: 0.1 g/mL at 20 °C, clear, colorless
BCS Class
3 · 3
FDA UNII
4 ABT0J945J · 4ABT0J945J
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H315-H319-H335
Precautionary statements
280 · P280-P305+P351+P338
Safety Statements
22 · 22-24/25
WGK Germany
1 · 1
RTECS
7350000 · XI7350000
F
3 · 3-8-10
HS Code
29362200 · 29362200
Storage Conditions · 1 item

The drug is not highly susceptible to atmospheric oxidation but should be protected from air and light. Thiamine hydrochloride tablets should be stored in tight, light-resistant containers at a temperature less than 40 degrees C, preferably between 15-30 degrees C. Thiamine hydrochloride injection should be protected from light and stored at a temperature less than 40 degrees C, preferably between 15-30 degrees C; freezing should be avoided.

Disposal Methods · 1 item

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.

Toxicology

Body Burden · 2 items

Vitamin B1 concentration in a typical healthy human body is approximately 30 mg of vitamine B1 in all forms with about 40-50% of this being in the muscles. Normal human blood contains about 90 ng/mL(1).

Vitamin B1 occurs in the human body as free thiamine and as thiamine monophosphate, thiamine triphosphate, and thiamine pyrophosphate. Beriberi is the disease resulting from severe thiamine deficiency; inadequate consumption of thiamine is the main cause of thiamine deficiency in underdeveloped countries. Alcoholism is the primary cause of thiamine deficiency in industrialized countries. Conditions resulting in an increased need for thiamine include strenuous physical exertion, fever, pregnancy, breast-feeding, and adolescent growth. Certain plants contain anti-thiamine factors which react with thiamine to form an oxidized, inactive product. Consuming large amounts of tea and coffee (including decaffeinated) have been associated with thiamine depletion in humans. Habitual consumption of raw freshwater fish, raw shellfish and ferns increase the risk of thiamine deficiency(1).

Interactions · 5 items

... 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.

Health EffectsThere are no reports available of adverse effects from consumption of excess thiamine by ingestion of food and supplements. [Wikipedia]
Food Survey Values · 2 items

Dietary Sources of Vitamin B1(1). [Table#839]

Whole grain cereals, legumes such as beans and lentils, nuts, lean pork and yeast are rich sources of vitamin B1(1). [Table#840]

Adverse Effects · 2 items

Asthma - Reversible bronchoconstriction (narrowing of bronchioles) initiated by the inhalation of irritating or allergenic agents.

Thiamine supplementation is reported to be well-tolerated and safe to use. A retrospective study on the adverse effects of thiamine supplementation among more than 300,000 patients found no serious side effects. However, some commonly reported adverse effects include nausea, urticaria, lethargy, ataxia, and impaired gut motility.

Exposure RoutesOral; parenteral (intravenous, intramuscular). Absorbed mainly from duodenum, by both active and passive processes
Milk Concentrations · 1 item

Vitamin B1 concentration range of 18.2 to 212.1 ug/L was reported in breast milk samples from Manila in a 1962 study of apparently healthy mothers. In another study, the mean vitamin B1 content of breast milk in women from India, Thailand, and the US was 153, 93-149, and 142 ug/L, respectively(1).

Toxicity Summary · 2 items

The human body excretes excess thiamine in the urine. No toxicity from high thiamine intake from food or supplements is evident. Food and Nutrition Board (FNB) concluded that excessive thiamine consumption might cause adverse effects despite a lack of solid evidence of toxicity. According to the Institute of Medicine, no established upper limit for thiamine intake that causes toxicity is reported in the literature.

It is thought that the mechanism of action of thiamine on endothelial cells is related to a reduction in intracellular protein glycation by redirecting the glycolytic flux. Thiamine is mainly the transport form of the vitamin, while the active forms are phosphorylated thiamine derivatives. There are five known natural thiamine phosphate derivatives: thiamine monophosphate (ThMP), thiamine diphosphate (ThDP), also sometimes called thiamine pyrophosphate (TPP), thiamine triphosphate (ThTP), and the recently discovered adenosine thiamine triphosphate (AThTP), and adenosine thiamine diphosphate. Each derivative has unique functions, however, most are involved as coenzymes.

Average Daily IntakeIn the US, the average dietary intake for thiamine for young adult men is about 2 mg/day and for young women, approximately 1.2 mg/day; over age 60, the average daily intake is about 1.4 and 1.1 mg/day for men and women, respectively(1).
Plant ConcentrationsNatural sources of vitamin B1 include whole cereal grains althouth processing of grains greatly reduces their thiamin content(1)/
Natural Pollution Sources · 1 item

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).

Human Toxicity Excerpts · 5 items

/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.

Safety data

F
3-8-10
wgk
1
rtecs
XI7350000
hs_code
29362200
Signal word
Warning
Symbol(GHS)
GHS07
safety_code
22-24/25
Hazard statements
H302-H315-H319-H335
Precautionary statements
P280-P305+P351+P338
Mechanism of Action · 2 items

It is thought that the mechanism of action of thiamine on endothelial cells is related to a reduction in intracellular protein glycation by redirecting the glycolytic flux. Thiamine is mainly the transport form of the vitamin, while the active forms are phosphorylated thiamine derivatives. Natural derivatives of thiamine phosphate, such as thiamine monophosphate (ThMP), thiamine diphosphate (ThDP), also sometimes called thiamine pyrophosphate (TPP), thiamine triphosphate (ThTP), and thiamine triphosphate (AThTP), that act as coenzymes in addition to their each unique biological functions.

Metabolic control analysis predicts that stimulators of transketolase enzyme synthesis such as thiamin (vitamin B-1) support a high rate of nucleic acid ribose synthesis necessary for tumor cell survival, chemotherapy resistance, and proliferation. Metabolic control analysis also predicts that transketolase inhibitor drugs will have the opposite effect on tumor cells. This may have important implications in the nutrition and future treatment of patients with cancer.

Biological Half-Life · 3 items

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.

Metabolism/Metabolites · 6 items

Hepatic

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.

Hepatic

MeSH Pharmacological ClassificationA group of water-soluble vitamins, some of which are COENZYMES.
Absorption, Distribution and Excretion · 6 items

Absorbed mainly from duodenum, by both active and passive processes

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.

Tissue LocationsAdipose Tissue
Cellular LocationsExtracellular
Metabolite PathwaysThiamine Metabolism

Uses & manufacturing

Uses · 6 items

An essential vitamin for carbohydrate metabolism and nerve function; Found in whole grains, meats, vegetables, milk, legumes, fruit, rice husks, and yeast; [Merck Index] Used as a nutritional supplement and flavoring agent for foods; [FDA] Used as a medicine, nutrient, in enriched flours, and other foods; [HSDB]

Prevention and treatment of vitamin B1 deficiency

Medicine, nutrition, enriched flours. Isolated usually as the chloride ... Available as thiamine hydrochloride and thiamine mononitrate

Reported uses

THERAPEUTIC CATEGORY: Vitamin (enzyme cofactor)

For more Uses (Complete) data for Vitamin B1 (6 total), please visit the HSDB record page.

ImpuritiesHeavy metals: not more than 10 mg/kg; water: not more than 5%.
U.S. Exports · 3 items

(1972) 1.34 X 10+7 g

(1975) 5.78 X 10+6 g

(1984) 3.36 X 10+7 g

U.S. Imports · 3 items

(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 · 3 items

(1972) Probably > 4.54 x 10+5 grams

(1975) Probably > 4.54 x 10+5 grams

(1986) No data

Consumption Patterns100% in prevention and treatment of vitamin B1 deficiency (1975)
Methods of Manufacturing · 3 items

... /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

Formulations/PreparationsBulk 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.
Use ClassificationFlavoring Agents -> JECFA Flavorings Index
General Manufacturing Information · 3 items

Thiazolium, 3-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-5-(2-hydroxyethyl)-4-methyl-, chloride (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.

Upstream & downstream products

Upstream raw materials

Thiamine Impurity 55-Pyrimidineaceticacid, 3,4-dihydro-2-methyl-4-oxo-, ethyl ester5-Pyrimidineacetamide, 4-amino-2-methyl-Pyrimidine, 4-chloro-5-(ethoxymethyl)-2-methyl-4-Pyrimidinamine, 5-(bromomethyl)-2-methyl- (9CI)4-Amino-5-aminomethyl-2-methylpyrimidineThiothiamine5-ethoxymethyl-2-methylpyrimidin-4-ylamineNSC 511275-(2-Hydroxyethyl)-4-methylthiazolePyruvic acid
Additional notes · 1 item

DefinitionChEBI: Thiamine(1+) is a primary alcohol that is 1,3-thiazol-3-ium substituted by (4-amino-2-methylpyrimidin-5-yl)methyl, methyl and 2-hydroxyethyl groups at positions 3, 4 and 5, respectively. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a primary alcohol and a vitamin B1. It is a conjugate base of a thiamine(2+).