<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2738</id>
  <title>T3D2696</title>
  <common-name>Thiamine</common-name>
  <description>Thiamine or thiamin, also known as vitamin B1, is a colorless compound with the chemical formula C12H17N4OS. It is soluble in water and insoluble in alcohol. Thiamine decomposes if heated. Thiamine was first discovered by Umetaro Suzuki in Japan when researching how rice bran cured patients of Beriberi. 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. Thiamine plays an important role in helping the body convert carbohydrates and fat into energy. It is essential for normal growth and development and helps to maintain proper functioning of the heart and the nervous and digestive systems. Thiamine cannot be stored in the body; however, once absorbed, the vitamin is concentrated in muscle tissue.</description>
  <cas>59-43-8</cas>
  <pubchem-id>1130</pubchem-id>
  <chemical-formula>C12H17N4OS</chemical-formula>
  <weight>265.112310</weight>
  <appearance>White powder.</appearance>
  <melting-point>248 dec°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>5E+005 mg/L</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral; parenteral (intravenous, intramuscular).Absorbed mainly from duodenum, by both active and passive processes</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>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.</mechanism-of-toxicity>
  <metabolism>Hepatic</metabolism>
  <toxicity>LD50: 8224 mg/kg (Oral, Mouse) (A308)LD50: 3710 mg/kg (Oral, Rat) (A308)</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>For the treatment of thiamine and niacin deficiency states, Korsakov's alcoholic psychosis, Wernicke-Korsakov syndrome, delirium, and peripheral neuritis. Thiamine (hydrochloride) is a food additive used to add a brothy/meaty flavor to gravies or soups.</use-source>
  <min-risk-level nil="true"/>
  <health-effects>There are no reports available of adverse effects from consumption of excess thiamine by ingestion of food and supplements. [Wikipedia]</health-effects>
  <symptoms></symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2009-07-21T20:26:09Z</created-at>
  <updated-at type="dateTime">2026-04-06T04:27:18Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Thiamine</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C00378</kegg-compound-id>
  <omim-id>213950
245400
248600
249270
308930
607483</omim-id>
  <chebi-id>18385</chebi-id>
  <biocyc-id>THIAMINE</biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Thiamine</stitch-id>
  <drugbank-id>DB00152</drugbank-id>
  <pdb-id>VIB</pdb-id>
  <actor-id>3147</actor-id>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N</moldb-smiles>
  <moldb-formula>C12H17N4OS</moldb-formula>
  <moldb-inchi>InChI=1S/C12H17N4OS/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)/q+1</moldb-inchi>
  <moldb-inchikey>JZRWCGZRTZMZEH-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">265.355</moldb-average-mass>
  <moldb-mono-mass type="decimal">265.112306876</moldb-mono-mass>
  <origin>Endogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id>HMDB00235</hmdb-id>
  <chembl-id>CHEMBL1547</chembl-id>
  <chemspider-id>1098</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>&lt;p&gt;Nobuyuki Kitamori, Masaya Maeno, Seiji Izuhara, &amp;#8220;Granules of thiamine salt and the production thereof.&amp;#8221; U.S. Patent US4702919, issued July, 1974.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002128</chemdb-id>
  <dsstox-id>DTXSID50220251</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00099891</susdat-id>
  <iupac>3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium</iupac>
</compound>
