92-35-3

Usage

Uses

Thiochrome is a selective M4 muscarinic receptor enhancer of acetylcholine affinity.

Purification Methods

Crystallise thiochrome from chloroform. The monohydrochloride has m 235-236o(dec) (from EtOH) and the dihydrochloride has m 237o(dec). [Beilstein 27 III/IV 9599.]

InChI:InChI=1/C12H14N4OS/c1-7-10(3-4-17)18-12-15-11-9(6-16(7)12)5-13-8(2)14-11/h5,17H,3-4,6H2,1-2H3

Upstream product

• 1820-94-6 2-amino-5-(2-hydroxyethyl)-4-methylthiazole 
• 731766-78-2 4-chloro-5-chloromethyl-2-methyl-pyrimidine 
• 40279-31-0 2-(4-methyl-2-methylsulfanyl-thiazol-5-yl)-ethanol 
• 2908-71-6 4-amino-5-bromomethyl-2-methylpyrimidine hydrobromide 
• 7403-34-1 7-methyl-3,4-dihydro-1H-pyrimido[4,5-d]pyrimidine-2-thione 
• 13051-49-5 5-Acetoxy-3-chloropentan-2-one 
• 23132-62-9 (4-amino-2-methyl-pyrimidin-5-ylmethyl)-dicarbothioamidoic acid ethyl ester 
• 64-17-5 ethanol 
• 108669-31-4 3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-tetrahydro-furo[2,3-d]thiazole-2-thione 
• 75-03-6 ethyl iodide 
• 120745-11-1 3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-3a-methyl-tetrahydro-furo[2,3-d]thiazol-2-ylideneamine 
• 64-19-7 acetic acid 
• 1153-39-5 3-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-4-hydroxy-5-(2-hydroxy-ethyl)-4-methyl-thiazolidine-2-thione 
• 67-03-8 Thiamine hydrochloride 

Relevant academic research and scientific papers

Green synthesis of gold nanoparticles using aqueous Aegle marmelos leaf extract and their application for thiamine detection

Nanoparticles of noble metals, especially gold nanoparticles are studied extensively because of their new and amazing properties. Among several synthesis techniques, green synthesis of nanoparticles is promising in recent years. In this study, we investigated the potential of Aegle marmelos leaf extract (LE) in reduction of HAuCl4 to form ～38.2 ± 10.5 nm spherical shape polyphenol capped gold nanoparticles. The stoichiometric proportion of the LE to HAuCl4 and the equilibrium time to complete the reduction process for the nanoparticle formation were also identified. The total reaction time was observed to be within ～30 min from the particle formation kinetics study. The as-synthesized gold nanoparticles capped with polyphenols of leaf extract were shown to be very effective for the detection of vitamin B or thiamine to a minimum concentration of ～0.5 μM.

Fluorometric Reaction Rate Method for the Determination of Thiamine

The reaction involving the oxidation of thiamine by Hg2+ in basic solutions to fluorescent thiochrome was studied.The initial rate of the reaction, measured as a change in fluorescence signal over 16 s, is linearily related to the thiamine concentration from a detection limit of 2 * 10-8 M up to 1 * 10-4 M.The applicability of the new method for determination of thiamine in vitamin-mineral preparations is demonstrated by investigation of the effect of potential interferences and by analysis of commercial and synthetic preparations.

Vitamin B1 sensor at neutral pH and improvement by cucurbit[7]uril

Thiamine deficiency is an important issue for many diseases and thus a facile method of detection is clinically important to improve the health of humans. For that purpose, we have developed a new thiamine sensor using starch stabilized copper nanoparticles (CSNP) at neutral pH and also improved the sensitivity of the sensor using cucurbit[7]uril (CB[7]) through host-guest chemistry. Often thiamine is not detected directly, but through the oxidation of thiamine to thiochrome (TC); TC is a fluorescent emitting molecule, through which thiamine has been measured indirectly. Here, we have demonstrated a new approach for a thiamine sensor, based on the formation of TC by the addition of hydrogen peroxide and CSNP. Unlike the other reported thiamine sensors, our method works advantageously at physiological pH conditions (pH 7, 27 °C). Furthermore, addition of CB[7] to TC, increased the sensitivity of the sensor approximately one order magnitude, through encapsulation; which can be reversed upon addition of a stronger competitive guest such as adamantylamine to confirm the encapsulation of TC. Thus, this new thiamine sensor not only performed well under physiological pH conditions, but also improved the fluorescence of TC, when encapsulated by CB[7].

Discriminative Detection of Glutathione in Cell Lysates Based on Oxidase-Like Activity of Magnetic Nanoporous Graphene

As the most abundant intracellular biothiol, glutathione (GSH) plays a central role in many cellular functions and has been proved to be associated with numerous clinical diseases. Nevertheless, it is still a challenge to detect GSH over other mercaptoamino acids owing to their similar structures and activities. In this paper, magnetic nanoporous graphene (MNPG) nanocomposites were prepared for the first time through partial combustion of graphene oxide (GO) and ferric chloride. Due to the combination of porous graphene and magnetic nanoparticles, the MNPG nanocomposites exhibited large specific surface area, fast mass, and electron transport kinetics, resulting in remarkable oxidase mimic activity and easy separation. On the basis of the inhibition effect of GSH on the MNPG-catalyzed oxidation of thiamine, a novel and simple method for fluorescence determination of GSH was established. The sensor displayed a good linear response in the range of 0.2-20 μM toward GSH with a limit of detection of 0.05 μM. High sensitivity and selectivity facilitated its practical application for discriminative detection of GSH levels in PC12 cell lysates. The presented assay will be a simple and powerful tool to monitor intracellular GSH levels for biomedical diagnosis. Furthermore, the MNPG nanocomposites will provide insights to construct nanoporous graphene-based hybrids and push forward the advancement of porous graphene for wide applications.

Reduction of cytochrome c in its reaction with thiamine and its structural analogs

The kinetics of reduction of ferricytochrome c in its reaction with thiamine and its O-substituted structural analogs in phosphate buffer at pH 7.5-7.8 were studied. The reduction rate is proportional to the concentration of thiamine or its derivatives. The dependence of the reaction rate on the oxidant concentration is characterized by negative deviations from linearity. In oxidation with ferricytochrome c, the reactivity of thiamine consdierably exceeds the reactivity of thiamine diphosphate and thiamine monophosphate, and in oxidation with ferricyanide the reaction rate increases in the order thiamine monophosphate thiamine thiamine diphosphate. With O-(2-norbornoyl)thiamine, O-(2-adamantyl)acetylthiamine, O-benzoylthiamine, O-(4-nitrobenzoyl)thiamine, or O-(5-nitro-2-chlorobenzoyl)thiamine, the rate of ferricytochrome c reduction is higher than with thiamine. Presumably, the electron transfer to the heme group of the oxidant is preceded by formation of a complex of ferricytochrome c with the neutral tricyclic form of the substrate.

Kinetics of oxidation of vitamin B1 and its O-acyl analogs with ferricyanide. A mechanistic model of thiamin-binding protein

The rate constants of oxidation of vitamin B1 and its O-acyl derivatives with ferricyanide in phosphate buffer at pH 7.2-7.8 were determined. The kinetics of the oxidation of thiamine, O-(2-norbornylcarbonyl)thiamine, O-(1-adamantylcarbonyl)thiamine, O-(5-methyl-1-adamantylcarbonyl)thiamine, O-(2-adamantylcarbonyl)thiamine, O-(2-adamantyl)acetylthiamine, and O-(1-adamantyl)acetylthiamine, followed by spectrophotometry by the formation of the corresponding thiochrome, fits first order both in substrate and in oxidant. With excess ferricyanide, the reciprocal of the apparent preudo-first-order rate constant increases with increasing ferrocyanide concentration. The intramolecular assistance by the hydrocarbon fragment of O-acyl-substituted thiamine is explained by the formation of an intermediate neutral tricyclic form of the substrate in a stage preceding electron transfer on ferricyanide. The reaction is assumed to mimic the effect of the hydrophobic environment during the transformation of vitamin B1 into the neutral tricyclic form on the surface of thiamin-binding protein.

MODEL REACTIONS OF THIAMINE DIPHOSPHATE-DEPENDENT ENZYMES. REACTION OF 2-(1-HYDROXYETHYL)THIAMINE WITH FERRICYANIDE

Reaction of 2-(1-hydroxyethyl)thiamine with ferricyanide in the presence of a base leads to elimination of acetaldehyde and formation of thiochrome and is characterized by first-order kinetics with respect to both the substrate and the oxidant.Ferricyanide ions inhibit this reaction.The reciprocal of the apparent pseudofirst-order rate constant increases with increase of ferrocyanide concentration when the concentration of ferricyanide is constant.The calculated rate constants k1 and k-1/k2 of decomposition of 2-(1-hydroxyethyl)thiamine and 2-(α-hydroxybenzyl)thiamine depend on the pH and the nature of the substituent in the C2α-position.The reaction mechanism includes deprotonation of the 4'-amino group, electron transfer to ferricyanide, and elimination of aldehyde from a radical intermediate containing an unpaired electron in the pyrimidine ring.The next reaction stages do not determine the overall reaction rate.It is assumed that oxidative decomposition of 2-(1-hydroxyethyl)thiamine simulates inactivation of thiamine diphosphate-dependent enzymes under the action of ferricyanide on the enzyme-substrate complex.

THIAMIN YLIDE: iSOLATION AND IDENTIFICATION

The action ot two equivalents of NaOEt on thiamin hydrochloride in EtOH gives a neutral compound.Spectroscopic data and its chemical behavior indicated that the compound is thiamin ylide 1.The chemical behaviors of 1 are entirely consistent with those of in situ generated thiamin ylide.