thiamine(1+) ion

Also known as vitamin B1, thiaminium, Thiamin, 2-[3-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-1-thia-3-azoniacyclopenta-2,4-dien-5-yl]ethanol, 2-[3-[(4-amino-2-methyl-pyrimidin-5-yl)methyl]-4-methyl-thiazol-5-yl]ethanol, VIB, Benerva, Bequin

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.

OverviewAI-generated

The thiamine(1+) ion is a chemical compound with the formula C₁₂H₁₇N₄OS⁺. Its IUPAC name is 2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethanol. The substance has a mass of 265.112 and a melting point of 249. It carries a charge of 1 and possesses two hydrogen bond donors and five hydrogen bond acceptors. The defined daily dose for this compound is 50.

Chemical properties include an xlogp value of 1 and a topological polar surface area of 104. The canonical SMILES representation is CC1=C(SC=[N+]1CC2=CN=C(N=C2N)C)CCO. A search for "thiamine(1+) ion" in PubMed yields 19,675 results. The subject is referenced by 1,516 other encyclopedia articles and is associated with the Commons category "Thiamine".

Synthesized by Vinony from 20 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

In the Vinony graph

Vinony's link graph records 1,516 inbound references to thiamine(1+) ion, and connects out to ion, cofactor and 1,3-thiazole.

Vinony files it under Aminopyrimidines, B vitamins and Cations.

Vinony links it to 78 Wikipedia language editions.

Key facts

Drug.image: Thiamine v2.svg
Drug.image_class: skin-invert-image
Drug.image2: Thiamine-cation-from-xtal-3D-bs-17.png
Drug.image_class2: bg-transparent
Drug.caption: Skeletal formula and ball-and-stick model of the thiamine cation
Drug.DailyMedID: Thiamine
Drug.routes_of_administration: By mouth, intravenous, intramuscular
Drug.class: Vitamin
Drug.ATC_prefix: A11
Drug.ATC_suffix: DA01
Drug.legal_US: OTC
Drug.bioavailability: 3.7% to 5.3% (Thiamine hydrochloride)
Drug.elimination_half life: 1–12 h
Drug.index_label: cation
Drug.index2_label: Cl− salt
Drug.CAS_number: 70-16-6
Drug.CAS_number2: 59-43-8 
Drug.CAS_supplemental: (Cl−.HCl)

via Wikipedia infobox

Chemical data

Formula: C12H17N4OS+
Molecular weight: 265.36 g/mol
IUPAC name: 2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethanol
SMILES: CC1=C(SC=[N+]1CC2=CN=C(N=C2N)C)CCO
InChIKey: JZRWCGZRTZMZEH-UHFFFAOYSA-N
XLogP: 1
Polar surface area: 104 Å²
H-bond donors: 2
H-bond acceptors: 5
Formal charge: 1

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1982
Admin. routes: parenteral

via ChEMBL · EBI

Research

19,675 papers

via PubMed

Wikidata facts

Has part: carbon
Mass: 265.112
Has use: medication

Show 11 more facts

medical condition treated: metabolic disease
Commons category: Thiamine
topic's main category: Category:Thiamine
canonical SMILES: CC1=C(SC=[N+]1CC2=CN=C(N=C2N)C)CCO
found in taxon: Trigonella foenum-graecum
chemical formula: C₁₂H₁₇N₄OS⁺
melting point: 249
subject has role: primary metabolite
different from: thymine
has characteristic: bitterness
defined daily dose: 50

Sources (9)

via Wikidata · CC0

~23 min read

Encyclopedic overview

21 sections

Contents

Definition
Deficiency
Biological functions
Thiamine pyrophosphate
Thiamine triphosphate
Adenosine derivatives
Medical uses
Dietary recommendations
Safety
Labeling
Sources
Food fortification
Synthesis
Biosynthesis
Laboratory synthesis
Industrial synthesis
Synthetic analogues
Absorption, metabolism and excretion
Interference
History
References

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.

Excerpted from Wikipedia’s “thiamine(1+) ion” article, available under the CC BY-SA 4.0 licence.