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2D Structure
Also known as: 67-03-8, Thiamine hcl, Aneurine hydrochloride, Vitamin b1 hydrochloride, Clotiamina, Thiamine chloride hydrochloride
Molecular Formula
C12H18Cl2N4OS
Molecular Weight
337.3  g/mol
InChI Key
DPJRMOMPQZCRJU-UHFFFAOYSA-M
FDA UNII
M572600E5P

Thiamine Hydrochloride is the hydrochloride salt form of thiamine, a vitamin essential for aerobic metabolism, cell growth, transmission of nerve impulses and acetylcholine synthesis. Upon hydrolysis, thiamine hydrochloride is phosphorylated by thiamine diphosphokinase to form active thiamine pyrophosphate (TPP), also known as cocarboxylase. TPP is a coenzyme for many enzymatic activities involving fatty acid, amino acid and carbohydrate metabolism.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethanol;chloride;hydrochloride
2.1.2 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
2.1.3 InChI Key
DPJRMOMPQZCRJU-UHFFFAOYSA-M
2.1.4 Canonical SMILES
CC1=C(SC=[N+]1CC2=CN=C(N=C2N)C)CCO.Cl.[Cl-]
2.2 Other Identifiers
2.2.1 UNII
M572600E5P
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Thiamine Chloride Hydrochloride

2.3.2 Depositor-Supplied Synonyms

1. 67-03-8

2. Thiamine Hcl

3. Aneurine Hydrochloride

4. Vitamin B1 Hydrochloride

5. Clotiamina

6. Thiamine Chloride Hydrochloride

7. Eskaphen

8. Betalin S

9. Vitamin B1

10. Thiamine Dichloride

11. Beatine

12. Begiolan

13. Benerva

14. Bethiazine

15. Bevitex

16. Bevitine

17. Bithiamin

18. Bivatin

19. Eskapen

20. Metabolin

21. Slowten

22. Thiaminal

23. Thiamol

24. Thiavit

25. Tiamidon

26. Tiaminal

27. Trophite

28. Vinothiam

29. Vitaneuron

30. Bedome

31. Beuion

32. Bivita

33. Berin

34. Bewon

35. Biuno

36. Hybee

37. Apate Drops

38. Lixa-beta

39. Thiamin Chloride

40. Thiaminum Hydrochloricum

41. Vetalin S

42. Thiaminium Chloride

43. Betaxin

44. Thiadoxine

45. Bequin

46. Thiamin Hydrochloride

47. Betabion Hydrochloride

48. Usaf Cb-20

49. Fema No. 3322

50. Vitamin B Hydrochloride

51. Thiaminium Chloride Hydrochloride

52. Thiamine(2+) Dichloride

53. Thiamine Monohydrochloride

54. Mfcd00012780

55. Betabion

56. Betamin

57. Biamine

58. Vitamin B(sub 1) Hydrochloride

59. Thiamine, Hydrochloride

60. Thiamine (hydrochloride)

61. Nsc-36226

62. 3-((4-amino-2-methylpyrimidin-5-yl)methyl)-5-(2-hydroxyethyl)-4-methylthiazol-3-ium Chloride Hydrochloride

63. Thiamine, Monohydrochloride

64. Thiamine Hcl (vitamin B1)

65. Vitamin B1 (thiamine Hcl)

66. 67-03-8 (hcl Salt)

67. Chebi:49105

68. Thiamine Hydrochloride (vitamin B1)

69. M572600e5p

70. Cas-67-03-8

71. Ncgc00017013-01

72. 2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethanol Chloride Hydrochloride

73. 2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethanol;chloride;hydrochloride

74. 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium Chloride Hydrochloride

75. Thiamine Hydrochloride 10 Microg/ml In Acetonitrile

76. Thiamine Chloride Hydrochloride;vitamin B1 Hydrochloride

77. Thd

78. Thiamin Dichloride

79. Smr000875246

80. Nsc36226

81. Ccris 1906

82. Vitamin Bl

83. Unii-m572600e5p

84. Vitamin B1 Hydrochloride (van)

85. Thiamine Hydrochloride [usp:jan]

86. Vitamin B(sup1)

87. Aneurinehydrochloride

88. Prestwick_441

89. Einecs 200-641-8

90. Nsc 36226

91. Thiamini Hydrochloridum

92. Thiamine Hcl (tn)

93. Vitamin B1hydrochloride

94. Ai3-18993

95. Thiazolium, Hydrochloride

96. Vitamin B1 [fhfi]

97. Dsstox_cid_20622

98. Dsstox_rid_79516

99. Thiamine Hcl [inci]

100. Thiazolium, Monohydrochloride

101. Dsstox_gsid_40622

102. Schembl41101

103. Mls001332447

104. Mls001332448

105. Thiamine Hydrochloride (usp)

106. Aneurine Hydrochloride Hydrate

107. Thiamine For System Suitability

108. Thiamine Chloride, Hydrochloride

109. Chembl1200941

110. Dtxsid0040622

111. Vitamin B1 Hydrochloride Hydrate

112. Thiamine, Chloride, Hydrochloride

113. Hms1569p04

114. Thiamine Hydrochloride [mi]

115. Bcp27971

116. Hy-n0680

117. Thiamine Hydrochloride [fcc]

118. Tox21_110736

119. S3211

120. Thiamine Hcl (vitamin B1) Solution

121. Thiamine Hydrochloride, P.a., 98%

122. Thiamine Hydrochloride [vandf]

123. Akos015905506

124. Thiamine Hydrochloride [mart.]

125. Thymine Hydrochloride [who-dd]

126. Ccg-220677

127. Chloride-hydrochloride Salt Of Thiamine

128. Cs-8164

129. Sb57886

130. Thiamine Hydrochloride [usp-rs]

131. Thiamine Hydrochloride [who-dd]

132. Thiamine Hydrochloride [who-ip]

133. Thiaminum Hydrochloricum [hpus]

134. Thiamine Chloride Hydrochloride (jp17)

135. Ncgc00017013-02

136. 2-{3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-5-yl}ethan- 1-ol, Chloride, Chloride

137. 3-((4-amino-2-methyl-5-pyrimidinyl)methyl)-5-(2-hydroxyethyl)-4-methylthiazolium Chloride Monohydrochloride

138. As-14151

139. Sy010871

140. Thiazolium, 3-((4-amino-2-methyl-5-pyrimidinyl)methyl)-5-(2-hydroxyethyl)-4-methyl- Chloride, Monohydrochloride

141. Db-054984

142. Thiamine Hydrochloride [ep Impurity]

143. Thiamine Hydrochloride [orange Book]

144. Thiamine Hydrochloride, >=98%, Fcc, Fg

145. Ft-0631293

146. Ft-0777960

147. T0181

148. Thiamine Chloride Hydrochloride [jan]

149. Thiamine Hydrochloride [ep Monograph]

150. Thiamine Hydrochloride [usp Monograph]

151. Thiamini Hydrochloridum [who-ip Latin]

152. D02094

153. Thiamine Hydrochloride 100 Microg/ml In Water

154. Thiamine Hydrochloride (b1), Analytical Standard

155. Thiamine Chloride, Hydrochloride [who-ip]

156. Q-201928

157. Thiamine Hydrochloride, Tested According To Ph.eur.

158. Q27121486

159. Thiamine Hydrochloride, Reagent Grade, >=99% (hplc)

160. Thiamine Hydrochloride, Saj Special Grade, >=98.5%

161. F0001-2415

162. F2173-0852

163. Thiamine Hydrochloride, Meets Usp Testing Specifications

164. Wln: T6n Cnj B1 Dz E1- At5k Csj D2q E1 &q &g &gh

165. Thiamine Hydrochloride, 99% (dry Wt.), May Cont. Up To 5% Water

166. Thiamine Hydrochloride (vitamin B1) 1.0 Mg/ml In Methanol (as Free Base)

167. Thiamine Hydrochloride, European Pharmacopoeia (ep) Reference Standard

168. Thiamine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

169. Thiamine For System Suitability, European Pharmacopoeia (ep) Reference Standard

170. Thiamine Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

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

172. 3-((4-amino-2-methyl-5-pyrimidinyl)methyl)-5-(2-hydroxyethyl)-4-m- Ethylthiazolium Chloride, Monohydrochloride

173. 3-[(4-azaniumyl-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium Dichloride

174. Thiamine Hcl (vitamin B1) Solution, 1.0 Mg/ml In Methanol (as Free Base), Ampule Of 1 Ml, Certified Reference Material

175. Thiamine Hydrochloride, Bioreagent, Suitable For Cell Culture, Suitable For Insect Cell Culture, Suitable For Plant Cell Culture

176. Thiamine Hydrochloride, Pharmagrade, Ep, Manufactured Under Appropriate Gmp Controls For Pharma Or Biopharmaceutical Production

177. Thiazolium, 3-((4-amino-2-methyl-5-pyrimidinyl)methyl)-5-(2-hydroxyethyl)-4-m- Ethyl, Chloride, Monohydrochloride

178. Thiazolium, 3-((4-amino-2-methyl-5-pyrimidinyl)methyl)-5-(2-hydroxyethyl)-4-methyl-, Chloride, Hydrochloride (1:1:1)

179. Thiazolium, 3-((4-amino-2-methyl-5-pyrimidinyl)methyl)-5-(2-hydroxyethyl)-4-methyl-, Chloride, Monohydrochloride

2.4 Create Date
2005-03-27
3 Chemical and Physical Properties
Molecular Weight 337.3 g/mol
Molecular Formula C12H18Cl2N4OS
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Exact Mass336.0578378 g/mol
Monoisotopic Mass336.0578378 g/mol
Topological Polar Surface Area104 Ų
Heavy Atom Count20
Formal Charge0
Complexity269
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count3
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameThiamine hydrochloride
Drug LabelThiamine Hydrochloride Injection, USP is a sterile solution of thiamine hydrochloride in Water for Injection for intramuscular (IM) or slow intravenous (IV) administration.Each mL contains: Thiamine hydrochloride 100 mg; chlorobutanol anhydrous (chlo...
Active IngredientThiamine hydrochloride
Dosage FormInjectable
RouteInjection
Strength100mg/ml
Market StatusPrescription
CompanyFresenius Kabi Usa; Mylan Institutional

2 of 2  
Drug NameThiamine hydrochloride
Drug LabelThiamine Hydrochloride Injection, USP is a sterile solution of thiamine hydrochloride in Water for Injection for intramuscular (IM) or slow intravenous (IV) administration.Each mL contains: Thiamine hydrochloride 100 mg; chlorobutanol anhydrous (chlo...
Active IngredientThiamine hydrochloride
Dosage FormInjectable
RouteInjection
Strength100mg/ml
Market StatusPrescription
CompanyFresenius Kabi Usa; Mylan Institutional

4.2 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).

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)


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.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)


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/

Sweetman SC (ed), Martindale: The Complete Drug Reference. London: Pharmaceutical Press (2009), p.1976-7.


/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.

PMID:7733128 Shimon I et al; Am J Med 98 (5): 485-90 (1995).


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


4.3 Drug Warning

Serious hypersensitivity/anaphylactic reactions can occur, especially after repeated administration. Deaths have resulted from IV or IM administration of thiamine.

Novak, K.M. (ed.). Drug Facts and Comparisons2008 Edition. Wolters Kluwer Health. St. Louis, Missouri 2008., p. 18


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...

PMID:9846348 Morinville V et al; Schweiz Med Wochenschr 128 (44): 1743-4 (1998).


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.

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., pg. 81, 1998. Available from, as of March 2, 2010: https://www.nap.edu/catalog/6015.html


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.

Sweetman SC (ed), Martindale: The Complete Drug Reference. London: Pharmaceutical Press (2009), p.1976.


For more Drug Warnings (Complete) data for Vitamin B1 (15 total), please visit the HSDB record page.


5 Pharmacology and Biochemistry
5.1 FDA Pharmacological Classification
5.1.1 Pharmacological Classes
Amino Acids [CS]; Blood Coagulation Factor [EPC]; Calcium [CS]; Calculi Dissolution Agent [EPC]; Cations, Divalent [CS]; Increased Coagulation Factor Activity [PE]; Increased Large Intestinal Motility [PE]; Inhibition Large Intestine Fluid/Electrolyte Absorption [PE]; Inhibition Small Intestine Fluid/Electrolyte Absorption [PE]; Magnesium Ion Exchange Activity [MoA]; Osmotic Activity [MoA]; Osmotic Laxative [EPC]; Potassium Compounds [CS]; Potassium Salt [EPC]; Stimulation Large Intestine Fluid/Electrolyte Secretion [PE]; Amino Acid [EPC]
5.2 Absorption, Distribution and Excretion

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.

Otten JJ, Hellwig JP, Meyers LD, eds; Dietary Reference Intakes: The Essential Guide to Nutrient Requirements, Washington, DC: The National Academies Press, 2006, p. 281


Thiamin is transported in blood in both erythrocytes and plasma and is excreted in the urine.

Otten JJ, Hellwig JP, Meyers LD, eds; Dietary Reference Intakes: The Essential Guide to Nutrient Requirements, Washington, DC: The National Academies Press, 2006, p.281


Thiamine is absorbed from the small intestine and is phosphorylated in the intestinal mucosa.

Furia, T.E. (ed.). CRC Handbook of Food Additives. 2nd ed. Cleveland: The Chemical Rubber Co., 1972., p. 89


The B vitamins are readily absorbed from the gastrointestinal tract, except in malabsorption syndromes. Thiamine is absorbed mainly in the duodenum.

USP Convention. USPDI-Drug Information for the Health Care Professional. 14th ed. Volume I. Rockville, MD: United States Pharmacopeial Convention, Inc., 1994. (Plus Updates)., p. 2647


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


5.3 Metabolism/Metabolites

Converted in vivo to thiamine diphosphate, a coenzyme in the decarboxylation of alpha-keto acids.

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 1598


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.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 248


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.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 229


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.

American Society of Health System Pharmacists; AHFS Drug Information 2009. Bethesda, MD. (2009)


5.4 Biological Half-Life

The biological half-life of the vitamin is in the range of 9-18 days.

Otten JJ, Hellwig JP, Meyers LD, eds; Dietary Reference Intakes: The Essential Guide to Nutrient Requirements, Washington, DC: The National Academies Press, 2006, p.281


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.

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., pg. 59, 1998. Available from, as of March 2, 2010: https://www.nap.edu/catalog/6015.html


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.

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., pg. 59, 1998. Available from, as of March 2, 2010: https://www.nap.edu/catalog/6015.html


5.5 Mechanism of Action

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.

PMID:10890024 Cascante M et al; Nutr Cancer 36 (2): 150-4 (2000).