Description

Bisbentiamine (CAS: 2667-89-2), also known as Benzoylthiamine disulfide or BTDS, is a synthetic derivative of thiamine (Vitamin B1) with enhanced bioavailability and therapeutic potential. Its molecular formula, C₃₈H₄₂N₈O₆S₂, reflects a complex structure designed for improved stability and efficacy. This compound is widely utilized in pharmaceutical research and nutraceutical applications due to its role in cellular energy metabolism and neuroprotective properties. Bisbentiamine is particularly valued for its ability to cross the blood-brain barrier more effectively than conventional thiamine derivatives, making it a focus of studies in neurodegenerative disorders and metabolic syndromes. Available in high-purity formulations (>98%), it is supplied as a white to off-white crystalline powder, ensuring consistency for research and industrial use. Store under recommended conditions (2-8°C, protected from light) to maintain stability.

Properties

• CAS Number: 2667-89-2
• Complexity: 1200
• IUPAC Name: [(E)-4-[(4-amino-2-methyl-pyrimidin-5-yl)methyl-formyl-amino]-3-[[(E)-2-[(4-amino-2-methyl-pyrimidin-5-yl)methyl-formyl-amino]-1-(2-benzoyloxyethyl)prop-1-enyl]disulfanyl]pent-3-enyl] benzoate
• InChI: InChI=1S/C38H42N8O6S2/c1-25(45(23-47)21-31-19-41-27(3)43-35(31)39)33(15-17-51-37(49)29-11-7-5-8-12-29)53-54-34(16-18-52-38(50)30-13-9-6-10-14-30)26(2)46(24-48)22-32-20-42-28(4)44-36(32)40/h5-14,19-20,23-24H,15-18,21-22H2,1-4H3,(H2,39,41,43)(H2,40,42,44)/b33-25+,34-26+
• InChI Key: IWXAZSAGYJHXPX-BCEWYCLDSA-N
• Exact Mass: 770.26687344
• Molecular Formula: C38H42N8O6S2
• Molecular Weight: 770.9
• SMILES: CC1=NC=C(C(=N1)N)CN(/C(=C(/SS/C(=C(/N(C=O)CC2=CN=C(N=C2N)C)C)/CCOC(=O)C3=CC=CC=C3)CCOC(=O)C4=CC=CC=C4)/C)C=O
• Topological: 247
• Monoisotopic Mass: 770.26687344
• Synonyms: Bisbentiamine, Beston, Beprocin, 2667-89-2, Bisbentiamina, Bisbentiaminum, Benzoylthiamine disulfide, Bisbentiamine [INN:JAN], O-Benzoylthiamine disulfide, Bisbentiaminum [INN-Latin], Bisbentiamina [INN-Spanish], Bis(O-benzoylthiamine)disulfide, UNII-MEI78CAM16, EINECS 220-206-6, MEI78CAM16, BRN 0741598, BISBENTIAMINE [MI], BISBENTIAMINE [INN], BISBENTIAMINE [JAN], BISBENTIAMINE [MART.], BISBENTIAMINE [WHO-DD], 5-25-12-00170 (Beilstein Handbook Reference), Formamide, N,N’-(dithiobis(2-(2-(benzoyloxy)ethyl)-1-methyl-2,1-ethenediyl))bis(N-((4-amino-2-methyl-5-pyrimidinyl)methyl)-, N,N’-(Dithiobis(2-(2-benzoyloxyethyl)-1-methylvinylene))bis(N-((4-amino-2-methyl-5-pyrimidinyl)methyl)formamide), Bisbentiaminum (INN-Latin), Bisbentiamina (INN-Spanish), Formamide, N,N’-(dithiobis(2-(2-hydroxyethyl)-1-methylvinylene))bis(N-((4-amino-1-methyl-5-pyrimidinyl)methyl)-, dibenzoate (ester), Formamide, N,N’-(dithiobis(2-(2-hydroxyethyl)-1-methylvinylene))bis(N-((4-amino-2-methyl-5-pyrimidinyl)methyl)-, dibenzoate (ester), BISBENTIAMINE (MART.), Beston (TN), BENZOYLTHIAMINDISULFID, DTXCID7028512, DTXSID7048586, 220-206-6, Formamide,N,N’-[dithiobis[2-[2-(benzoyloxy)ethyl]-1-methyl-2,1-ethenediyl]]bis[N-[(4-amino-2-methyl-5-pyrimidinyl)methyl]-, BTDS, Bisbentiamin, NCGC00183879-01, MLS006010791, SCHEMBL1649194, CHEMBL1987005, SCHEMBL27397838, CHEBI:31288, IWXAZSAGYJHXPX-BCEWYCLDSA-N, FB41608, NCGC00183879-02, AS-17379, SMR001827643, NS00007828, H37447, SR-01000944879, SR-01000944879-1, Q27283980, Formamide, N,N’-(dithiobis(2-(2-hydroxyethyl)-1-methylvinylene))bis(N-((4-amino-2-methyl- 5-pyrimidinyl)methyl)-, dibenzoate (ester)

Bisbentiamine is primarily investigated for its neuroprotective and metabolic-enhancing effects, particularly in conditions like diabetic neuropathy and Alzheimer’s disease. Its superior bioavailability compared to thiamine makes it a candidate for treating vitamin B1 deficiencies with compromised absorption. Researchers also explore its antioxidant properties in mitigating oxidative stress-related cellular damage. In preclinical models, it has shown promise in improving cognitive function and peripheral nerve health.

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