Thiamine

Overview

Thiamine, also known as thiamin and vitamin B₁, is a vitamin – an essential micronutrient for humans and animals. It is found in food and commercially synthesized to be a dietary supplement or medication. Phosphorylated forms of thiamine are required for some metabolic reactions, including the breakdown of glucose and amino acids.[1–4] WP

Food sources of thiamine include whole grains, legumes, and some meats and fish. Grain processing removes much of the vitamin content, so in many countries cereals and flours are enriched with thiamine. Supplements and medications are available to treat and prevent thiamine deficiency and the disorders that result from it such as beriberi and Wernicke encephalopathy. They are also used to treat maple syrup urine disease and Leigh syndrome. Supplements and medications are typically taken by mouth, but may also be given by intravenous or intramuscular injection.[1][2][4][5] WP

Thiamine supplements are generally well tolerated. Allergic reactions, including anaphylaxis, may occur when repeated doses are given by injection. Thiamine is on the World Health Organization's List of Essential Medicines. It is available as a generic medication, and in some countries as a non-prescription dietary supplement. In 2023, it was the 305th most commonly prescribed medication in the United States, with more than 300,000 prescriptions.[1][3][5–8] WP

Uses, dosage and effects

Medical uses

During pregnancy, thiamine is sent to the fetus via the placenta. Pregnant women have a greater requirement for the vitamin than other adults, especially during the third trimester. Pregnant women with hyperemesis gravidarum are at an increased risk of thiamine deficiency due to losses when vomiting. In lactating women, thiamine is delivered in breast milk even if it results in thiamine deficiency in the mother.[1][2][9][10][11] WP

Thiamine is important not only for mitochondrial membrane development, but also for synaptic membrane function. It has also been suggested that a deficiency hinders brain development in infants and may be a cause of sudden infant death syndrome.[12][13] WP

Risks and side effects

Safety

Thiamine is generally well tolerated and non-toxic when administered orally. There are rare reports of adverse side effects when thiamine is given intravenously, including allergic reactions, nausea, lethargy, and impaired coordination.[5][14][15] WP

History

History

Thiamine was the first of the water-soluble vitamins to be isolated. The earliest observations in humans and in chickens had shown that diets of primarily polished white rice caused beriberi, but did not attribute it to the absence of a previously unknown essential nutrient.[16][17][18] WP

In 1884, Takaki Kanehiro, a surgeon general in the Imperial Japanese Navy, rejected the previous germ theory for beriberi and suggested instead that the disease was due to insufficiencies in the diet. Switching diets on a navy ship, he discovered that replacing a diet of white rice only with one also containing barley, meat, milk, bread, and vegetables, nearly eliminated beriberi on a nine-month sea voyage. However, Takaki had added many foods to the successful diet and he incorrectly attributed the benefit to increased protein intake, as vitamins were unknown at the time. The Navy was not convinced of the need for such an expensive program of dietary improvement, and many men continued to die of beriberi, even during the Russo-Japanese War of 1904–05. Not until 1905, after the anti-beriberi factor had been discovered in rice bran (removed by polishing into white rice) and in barley bran, was Takaki's experiment rewarded. He was made a baron in the Japanese peerage system, after which he was affectionately called "Barley Baron".[17] WP

The specific connection to grain was made in 1897 by Christiaan Eijkman, a military doctor in the Dutch East Indies, who discovered that fowl fed on a diet of cooked, polished rice developed paralysis that could be reversed by discontinuing rice polishing. He attributed beriberi to the high levels of starch in rice being toxic. He believed that the toxicity was countered in a compound present in the rice polishings. An associate, Gerrit Grijns, correctly interpreted the connection between excessive consumption of polished rice and beriberi in 1901: He concluded that rice contains an essential nutrient in the outer layers of the grain that is removed by polishing. Eijkman was eventually awarded the Nobel Prize in Physiology and Medicine in 1929, because his observations led to the discovery of vitamins.[18][19][20] WP

In 1910, a Japanese agricultural chemist of Tokyo Imperial University, Umetaro Suzuki, isolated a water-soluble thiamine compound from rice bran, which he named aberic acid. (He later renamed it Orizanin.) He described the compound as not only an anti-beriberi factor, but also as being essential to human nutrition; however, this finding failed to gain publicity outside of Japan, because a claim that the compound was a new finding was omitted in translation of his publication from Japanese to German. In 1911 a Polish biochemist Casimir Funk isolated the antineuritic substance from rice bran (the modern thiamine) that he called a "vitamine" (on account of its containing an amino group). However, Funk did not completely characterize its chemical structure. Dutch chemists, Barend Coenraad Petrus Jansen and his closest collaborator Willem Frederik Donath, went on to isolate and crystallize the active agent in 1926, whose structure was determined by Robert Runnels Williams, in 1934. Thiamine was named by the Williams team as a portmanteau of "thio" (meaning sulfur-containing) and "vitamin". The term "vitamin" coming indirectly, by way of Funk, from the amine group of thiamine itself (although by this time, vitamins were known to not always be amines, for example, vitamin C). Thiamine was also synthesized by the Williams group in 1936.[16][21–24] WP

Sir Rudolph Peters, in Oxford, used pigeons to understand how thiamine deficiency results in the pathological-physiological symptoms of beriberi. Pigeons fed exclusively on polished rice developed opisthotonos, a condition characterized by head retraction. If not treated, the animals died after a few days. Administration of thiamine after opisthotonos was observed led to a complete cure within 30 minutes. As no morphological modifications were seen in the brain of the pigeons before and after treatment with thiamine, Peters introduced the concept of a biochemical-induced injury. In 1937, Lohmann and Schuster showed that the diphosphorylated thiamine derivative, TPP, was a cofactor required for the oxidative decarboxylation of pyruvate.[25][26] WP

Chemistry

Formula

C12H17N4OS+ PC

Formula (Wikipedia infobox)

C12H17N4OS WP⚠ Wikipedia and PubChem give different formulas. Both are shown as each source has it.

Note

⚠ The PubChem record carries a charge, so it may describe an ion or salt of this substance rather than the substance itself.

CAS number

70-16-6 PC

Molar mass (g/mol)

265.36 PC

IUPAC name (computed by PubChem)

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

SMILES

CC1=C(SC=[N+]1CC2=CN=C(N=C2N)C)CCO PC

InChIKey

JZRWCGZRTZMZEH-UHFFFAOYSA-N PC

PubChem CID

1130

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Journal / agency Thiamin: Fact Sheet for Health Professionals. 9 February 2023
2. Other Thiamin. 2025
3. Journal / agency Thiamine
4. Journal / agency Whitfield KC, Bourassa MW, Adamolekun B, Bergeron G, Bettendorff L, Brown KH, Cox L, Fattal-Valevski A, Fischer PR, Frank EL, Hiffler L, Hlaing LM, Jefferds ME, Kapner H, Kounnavong S, Mousavi MP, Roth DE, Tsaloglou MN, Wieringa F, Combs GF. Thiamine deficiency disorders: diagnosis, prevalence, and a roadmap for global control programs. Annals of the New York Academy of Sciences. October 2018. doi:10.1111/nyas.13919 · PMID 30151974 · PMC6392124
5. Other American Society of Health-System Pharmacists. Thiamine Hydrochloride. 12 January 2025
6. Other Kliegman RM, Stanton B. Nelson Textbook of Pediatrics. 2016
7. Other World Health Organization model list of essential medicines: 21st list 2019. 2019
8. Other Kane SP. Thiamine Drug Usage Statistics, United States, 2014 - 2023
9. Journal / agency Oudman E, Wijnia JW, Oey M, van Dam M, Painter RC, Postma A. Wernicke's encephalopathy in hyperemesis gravidarum: A systematic review. European Journal of Obstetrics, Gynecology, and Reproductive Biology. May 2019. doi:10.1016/j.ejogrb.2019.03.006 · PMID 30889425
10. Other Institute of Medicine. Dietary Reference Intakes for Thiamin, Riboflavin, Niacin, Vitamin B6, Folate, Vitamin B12, Pantothenic Acid, Biotin, and Choline. 1998
11. Journal / agency Butterworth RF. Maternal thiamine deficiency: still a problem in some world communities. The American Journal of Clinical Nutrition. December 2001. doi:10.1093/ajcn/74.6.712 · PMID 11722950
12. Journal / agency Kloss O, Eskin NA, Suh M. Thiamin deficiency on fetal brain development with and without prenatal alcohol exposure. Biochemistry and Cell Biology. April 2018. doi:10.1139/bcb-2017-0082 · PMID 28915355
13. Journal / agency Lonsdale D. A review of the biochemistry, metabolism and clinical benefits of thiamin(e) and its derivatives. Evidence-Based Complementary and Alternative Medicine. March 2006. doi:10.1093/ecam/nek009 · PMID 16550223 · PMC1375232
14. Other Tolerable Upper Intake Levels For Vitamins And Minerals. 2006
15. Other Bettendorff L. Present Knowledge in Nutrition, Eleventh Edition. 2020
16. Journal / agency Suzuki U, Shimamura T. Active constituent of rice grits preventing bird polyneuritis. Tokyo Kagaku Kaishi. 1911. doi:10.1246/nikkashi1880.32.4
17. Other McCollum EV. A History of Nutrition. 1957
18. Journal / agency Eijkman C. Eine Beriberiähnliche Krankheit der Hühner. Archiv für Pathologische Anatomie und Physiologie und für Klinische Medicin. 1897. doi:10.1007/BF01937576
19. Other The Nobel Prize and the Discovery of Vitamins
20. Journal / agency Grijns G. Over polyneuritis gallinarum. Geneeskundig Tijdschrift voor Nederlandsch-Indië (Medical Journal for the Dutch East Indies). 1901
21. Journal / agency Funk C. On the chemical nature of the substance which cures polyneuritis in birds induced by a diet of polished rice. The Journal of Physiology. December 1911. doi:10.1113/jphysiol.1911.sp001481 · PMID 16993097 · PMC1512869
22. Journal / agency Funk C. The etiology of the deficiency diseases. Beri-beri, polyneuritis in birds, epidemic dropsy, scurvy, experimental scurvy in animals, infantile scurvy, ship beri-beri, pellagra. Journal of State Medicine. 1912
23. Journal / agency Jansen BC, Donath WF. On the isolation of antiberiberi vitamin. Proc. Kon. Ned. Akad. Wet. 1926
24. Journal / agency Williams RR, Cline JK. Synthesis of Vitamin B₁. Journal of the American Chemical Society. 1936. doi:10.1021/ja01299a505
25. Journal / agency Peters RA. The biochemical lesion in vitamin B₁ deficiency. Application of modern biochemical analysis in its diagnosis. Lancet. 1936. doi:10.1016/S0140-6736(01)28025-8
26. Journal / agency Lohmann K, Schuster P. Untersuchungen über die Cocarboxylase. Biochem. Z. 1937

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.