What molecule am I?
Pyridoxine is a water-soluble form of vitamin B6 that converts to pyridoxal 5�-phosphate1 (PLP), the active form of the vitamin, in the body. Pyridoxine appeared in the literature in 1938 and 1939 in a flurry of articles by American and German researchers.
The work in the United States was performed by chemists at Merck (Rahway, NJ). Eric T. Stiller, John C. Keresztesy, and Joseph R. Stevens 2, which was then considered to be the main form of vitamin B6. Stanton A. Harris and Karl Folkers followed up by 3 in nine steps beginning with 1-ethoxypentane-2,4-dione and cyanoacetamide4.
The German work was at the Kaiser Wilhelm Institute for Chemistry (Heidelberg; now the Max Planck Institute for Chemistry). Their term for vitamin B6/pyridoxine was adermin.
Some plants and microorganisms produce pyridoxine; but animals, including humans, do not. The compound is present in many foods but may need to be supplemented. Vitamin B6 supplements contain the hydrochloride more frequently than the free base.
Pyridoxine has been reported to resolve psychosis induced by isoniazid5, an antibiotic used to treat tuberculosis. In a 2024 review of isoniazid-induced psychosis cases, Mahadev Rao at the Manipal Academy of Higher Education (India) and colleagues there and at other Indian institutions proposed that the metabolism of isoniazid may and lead to a pyridoxine deficiency. The authors concluded that additional research is required to understand the risk factors associated with isoniazid and to recommend whether and how much supplemental pyridoxine should be administered to manage the psychosis.
1. CAS Reg. No. 54-47-7.
2. Then called 2-methyl-3-hydroxy-4,5-di(hydroxymethyl)pyridine.
3. CAS Reg. No. 58-56-0.
4. CAS Reg. No. 107-91-5.
5. CAS Reg. No. 54-85-3.
Pyridoxine hazard information
| Hazard class** | GHS code and hazard statement | |
|---|---|---|
Skin corrosion/irritation, category 2 | H315—Causes skin irritation |  |
| Serious eye damage/eye irritation, category 2A | H319—Causes serious eye irritation | |
| Specific target organ toxicity, single exposure, respiratory tract irritation, category 3 | H335—May cause respiratory irritation | |
*One safety data sheet contains this information; others report “not a hazardous substance or mixture�.
**Globally Harmonized System (GHS) of Classification and Labeling of Chemicals. .
Molecules from the Journals
Lenacapavir1 is an antiretroviral drug that was approved in 2022 by the United States, Canada, and the European Union for treating HIV/AIDS. Developed by Gilead Sciences (Foster City, CA), it is the first capsid inhibitor medication to be approved by FDA.
In 2020, Stephen R. Yant and dozens of colleagues, mostly at Gilead, described the , then known as GS-6207. Then last November, Moupali Das at Gilead and more than 50 coauthors in North America, South America, Africa, and Asia described a study in which 3265 male and gender-diverse individuals were treated twice annually with lenacapavir or daily with an established HIV medication. Lenacapavir in terms of lower HIV incidence by a ratio of �2.5:1.
Trimethylaluminum2 is an organometallic compound that is a colorless, pyrophoric liquid. Despite its “trimethyl� prefix, it is a dimer at ambient conditions, with the empirical formula Al2Me6. An early was reported by Aristid V. Grosse and Julian M. Mavity at Universal Oil Products (then in Riverside, IL)
Al2Me6 has applications in catalysis, semiconductors, and photovoltaics. Earlier this month, Takeshi Kobayashi, Long Qi, Aaron D. Sadow, and co-workers at Iowa State University (Ames) described its use as an activator for a zeolite-confined lanthanum borohydride catalyst. The activated catalyst, with the formula La(BH4)2(AlMe3)-Ph3Si-HY30, between pinacolborane3 and benzene with improved yields and turnover numbers compared with the unactivated catalyst.
1. CAS Reg. No. 2189684-44-2.
2. CAS Reg. No. 75-24-1.
3. CAS Reg. No. 25015-63-8.
Molecules from the Journals
MOTW briefly describes noteworthy molecules that appeared in recent ACS journal articles. See this week's edition.
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Pyridoxine fast facts
| CAS Reg. No. | 65-23-6 |
| SciFindern name | 3,4-Pyridinedimethanol, 5-hydroxy-6-methyl- |
| Empirical formula | C8H11NO3 |
| Molar mass | 169.18 g/mol |
| Appearance | White crystals or powder |
| Melting point | 159�162 ºC |
| Water solubility | 79 g/L |
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