U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ACHIRAL
Molecular Formula C12H17N4OS.Cl.ClH
Molecular Weight 337.269
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THIAMINE HYDROCHLORIDE

SMILES

Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC2=C(N)N=C(C)N=C2

InChI

InChIKey=DPJRMOMPQZCRJU-UHFFFAOYSA-M
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

HIDE SMILES / InChI

Molecular Formula C12H16N4OS
Molecular Weight 264.347
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Thiamine, also known as vitamin B1, plays a key role in the human metabolism. It is present in many dietary sources such as meats, eggs, fish, beans and peas, nuts, and whole grains. Upon administration thiamine is converted by thiamine pyrophosphokinase-1 (TPK1) to the active form, thiamine pyrophosphate, which serves as a cofactor for enzymes involved in the TCA cycle and the non-oxidative part of the pentose phosphate pathway. The lack of thiamine may cause the thiamine deficiency. The classical syndrome caused primarily by thiamine deficiency in humans is beriberi, however, symptoms of thiamine deficiency also include congestive heart failure, metabolic acidosis, confusion, ataxia and seizures. Thiamine is a component of many vitamin complexes, which are approved for the treatmen and prevention of general vitamin deficiency, including the thiamine deficiency.

CNS Activity

Curator's Comment: The transport of thiamine across the blood brain barrier was shown in rats.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q9H3S4
Gene ID: 27010.0
Gene Symbol: TPK1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
M.V.I.-12

Approved Use

M.V.I.-12 Unit Vial, is indicated for the prevention of vitamin deficiency in adults and children aged 11 years and above who are on warfarin anticoagulant therapy receiving home parenteral nutrition.

Launch Date

1953
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
40 nM
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
39 nM
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
95 nM
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
113 nM
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
386 nM
1500 mg single, oral
dose: 1500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
397 nM
1500 mg single, oral
dose: 1500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
214 nM × h
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
177 nM × h
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
623 nM × h
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
612 nM × h
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
2046 nM × h
1500 mg single, oral
dose: 1500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
2059 nM × h
1500 mg single, oral
dose: 1500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.92 h
500 mg single, oral
dose: 500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
4.78 h
1500 mg single, oral
dose: 1500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
2.97 h
1500 mg single, oral
dose: 1500 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
THIAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
Doses

Doses

DosePopulationAdverse events​
500 mg single, intravenous
Highest studied dose
Dose: 500 mg
Route: intravenous
Route: single
Dose: 500 mg
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sex: unknown
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Cloning of the human thiamine transporter, a member of the folate transporter family.
1999 Nov 5
Effect of thiamine hydrochloride on lead induced lipid peroxidation in rat liver and kidney.
2000 Aug
Mitochondrial myopathy and familial thiamine deficiency.
2000 Jul
Low plasma thiamine levels in elder patients admitted through the emergency department.
2000 Oct
[Evaluation of vitamin and immune status of patients with chronic palatal tonsillitis].
2001
Effects of vitamins on hepatic nuclear binding of L-tryptophan.
2001
Thiamine-responsive acute neurological disorders in nonalcoholic patients.
2001
Nutritional evaluation of ethanol-extracted lentil flours.
2001 Apr
Analysis of slc19a2, on 1q23.3 encoding a thiamine transporter as a candidate gene for type 2 diabetes mellitus in pima indians.
2001 Apr
Suppression of the accumulation of triosephosphates and increased formation of methylglyoxal in human red blood cells during hyperglycaemia by thiamine in vitro.
2001 Apr
The multifaceted and widespread pathology of magnesium deficiency.
2001 Feb
Aroma extract dilution analysis of a beeflike process flavor from extruded enzyme-hydrolyzed soybean protein.
2001 Feb
Evidence for non-enzymatic glycosylation in Escherichia coli.
2001 Feb
In vivo and in vitro proton NMR spectroscopic studies of thiamine-deficient rat brains.
2001 Feb
Chorea induced by thiamine deficiency in hemodialysis patients.
2001 Feb
Glucose induced IEG expression in the thiamin-deficient rat brain.
2001 Feb 16
Probing the mechanism of inactivation of human pyruvate dehydrogenase by phosphorylation of three sites.
2001 Feb 23
Cresol red thallium acetate sucrose inulin (CTSI) agar for the selective recovery of Carnobacterium spp.
2001 Feb 28
Nutritional evaluation of some processed catering foods.
2001 Jan
Thiamin treatment and working memory function of alcohol-dependent people: preliminary findings.
2001 Jan
Manothermosonication of foods and food-resembling systems: effect on nutrient content and nonenzymatic browning.
2001 Jan
In vivo microdialysis in an animal model of neurological disease: thiamine deficiency (Wernicke) encephalopathy.
2001 Jan
Solution structure of ThiS and implications for the evolutionary roots of ubiquitin.
2001 Jan
Impact of the reduced folate carrier on the accumulation of active thiamin metabolites in murine leukemia cells.
2001 Jan 12
Molecular cloning of human thiamin pyrophosphokinase.
2001 Jan 26
Isolation and characterization of a human thiamine pyrophosphokinase cDNA.
2001 Jan 26
Thiamine-responsive megaloblastic anemia syndrome: a disorder of high-affinity thiamine transport.
2001 Jan-Feb
Vitamin requirements of the cultured flesh fly cells, Sarcophaga peregrina (Diptera, Sarcophagidae).
2001 Jan-Feb
Effects of glucose, vitamins, and DO concentrations on pyruvate fermentation using Torulopsis glabrata IFO 0005 with metabolic flux analysis.
2001 Jan-Feb
Low thiamine intake and risk of cataract.
2001 Jul
Nerve conduction changes in patients with mitochondrial diseases treated with dichloroacetate.
2001 Jul
Mechanism of thiamine uptake by human colonocytes: studies with cultured colonic epithelial cell line NCM460.
2001 Jul
No association between DLST gene and Alzheimer's disease or Wernicke-Korsakoff syndrome.
2001 Jul-Aug
Vitamin B intake and status in healthy Havanan men, 2 years after the Cuban neuropathy epidemic.
2001 Jun
Sulfur compounds reduce potato toxins during extrusion cooking.
2001 Jun
Slc19a2: cloning and characterization of the murine thiamin transporter cDNA and genomic sequence, the orthologue of the human TRMA gene.
2001 Jun
Simultaneous determination of thiamine and pyridoxine in pharmaceuticals by using a single flow-through biparameter sensor.
2001 Jun
Comparison of ion-pair and amide-based column reversed-phase liquid chromatography for the separation of thiamine-related compounds.
2001 Jun 15
Catalytic acid-base groups in yeast pyruvate decarboxylase. 1. Site-directed mutagenesis and steady-state kinetic studies on the enzyme with the D28A, H114F, H115F, and E477Q substitutions.
2001 Jun 26
Crystal structure of thiamin pyrophosphokinase.
2001 Jun 29
Relationships between dietary intake and cognitive function level in Korean elderly people.
2001 Mar
The value of oral thiamine.
2001 Mar-Apr
[Other drugs administered with TPN solution].
2001 May
[Metabolic acidosis induced by TPN].
2001 May
Wernicke's encephalopathy in a non-alcoholic man: case report and brief review.
2001 May
Application of liquid chromatography to the simultaneous determination of acetylsalicylic acid, caffeine, codeine, paracetamol, pyridoxine, and thiamine in pharmaceutical preparations.
2001 May-Jun
The role of the cysteine residues of ThiI in the generation of 4-thiouridine in tRNA.
2001 Sep 7
Patents

Sample Use Guides

The starting dose (as a component of M.V.I.–12) is one 10 mL daily dose added directly to an intravenous fluid.
Route of Administration: Intravenous
Human Caco-2 cells were incubated (37 Celsius) in Krebs-Ringer buffer (pH 7.4) for different periods of time in the presence of 0.1 uM and 10 uM thiamine. The uptake study demonstrated that thiamine is transported across the cell membrane with Michaelis-Menten constant of 3.18 uM.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:45:54 GMT 2025
Edited
by admin
on Mon Mar 31 18:45:54 GMT 2025
Record UNII
M572600E5P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
THIAMINE HYDROCHLORIDE
EP   FCC   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
Common Name English
THIAMINE HCL
INCI  
INCI  
Preferred Name English
FEMA NO. 3322
Code English
BETAMIN
Brand Name English
ESKAPHEN
Common Name English
THIAMINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
THIAMINUM HYDROCHLORICUM [HPUS]
Common Name English
CLOTIAMINA
Common Name English
THIAMINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
THIAMINUM HYDROCHLORICUM
HPUS  
Common Name English
THIAMINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
THIAMINE HYDROCHLORIDE [MART.]
Common Name English
THIAMINE HYDROCHLORIDE [EP IMPURITY]
Common Name English
THIAMINE HYDROCHLORIDE [FCC]
Common Name English
THIAMINE HYDROCHLORIDE [USP-RS]
Common Name English
THIAMINE CHLORIDE, HYDROCHLORIDE [WHO-IP]
Common Name English
THIAZOLIUM, 3-((4-AMINO-2-METHYL-5-PYRIMIDINYL)METHYL)-5-(2-HYDROXYETHYL)-4-METHYL-, CHLORIDE, MONOHYDROCHLORIDE
Common Name English
THIAMINE CHLORIDE HYDROCHLORIDE
JAN  
Common Name English
Thymine hydrochloride [WHO-DD]
Common Name English
THIAMINI HYDROCHLORIDUM [WHO-IP LATIN]
Common Name English
VITAMIN B1 [FHFI]
Common Name English
THIAMINE CHLORIDE HYDROCHLORIDE [JAN]
Common Name English
THIAMINE HYDROCHLORIDE [MI]
Common Name English
BETALIN S
Brand Name English
THIAMINE HYDROCHLORIDE [VANDF]
Common Name English
THIAMINE HYDROCHLORIDE [WHO-IP]
Common Name English
NSC-36226
Code English
Thiamine hydrochloride [WHO-DD]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 310.529
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
NCI_THESAURUS C26017
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
CFR 21 CFR 184.1875
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
JECFA EVALUATION THIAMINE HYDROCHLORIDE
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
DSLD 2667 (Number of products:2178)
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
Code System Code Type Description
PUBCHEM
6202
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
JECFA MONOGRAPH
963
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
EPA CompTox
DTXSID0040622
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
FDA UNII
M572600E5P
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
MERCK INDEX
m10717
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY Merck Index
CHEBI
49105
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
EVMPD
SUB04798MIG
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-641-8
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
SMS_ID
100000091092
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
RXCUI
235355
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY RxNorm
NSC
36226
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
RS_ITEM_NUM
1656002
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
DRUG BANK
DBSALT000205
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
DAILYMED
M572600E5P
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
THIAMINE HYDROCHLORIDE
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY Description: Colourless crystals or a white or yellowish white, crystalline powder; odour, slight and characteristic. Solubility: Soluble in 1 part of water and in 100 parts of ethanol (~750 g/l) TS; practically insoluble in acetone R and ether R. Category: Component of vitamin B. Storage: Thiamine hydrochloride should be kept in a tightly closed, non-metallic container, protected from light. Additional information: Even in the absence of light, Thiamine hydrochloride is gradually degraded on exposure to a humidatmosphere, the decomposition being faster at higher temperatures. When exposed to air, the anhydrous product rapidly absorbsabout 4 g of water per 100 g. Melting temperature, about 248 ?C with some decomposition. In solution at pH 4.0 or less, it loses its activity only very slowly. Neutral and alkaline solutions deteriorate rapidly, especially in contact with air. Definition: Thiamine hydrochloride contains not less than 98.0% and not more than 101.0% of C12H17ClN4OS,HCl, calculated with reference to the dried substance.
NCI_THESAURUS
C48025
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
CAS
67-03-8
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
ChEMBL
CHEMBL1547
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
EVMPD
SUB179894
Created by admin on Mon Mar 31 18:45:54 GMT 2025 , Edited by admin on Mon Mar 31 18:45:54 GMT 2025
PRIMARY
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