Lutidine
Lutidine is the trivial name used to describe the chemical compounds which are dimethyl derivatives of pyridine. They were discovered in Dippel's oil and named (as an anagram of toluidine, with which they share their empirical formula) by Thomas Anderson in 1851.[1] Their chemical properties resemble those of pyridine, although the presence of the methyl groups may prohibit some of the more straightforward reactions. Lutidine comes in several isomers:
- 2,3-Lutidine (2,3-dimethylpyridine)
- 2,4-Lutidine (2,4-dimethylpyridine)
- 2,5-Lutidine (2,5-dimethylpyridine)
- 2,6-Lutidine (2,6-dimethylpyridine)
- 3,4-Lutidine (3,4-dimethylpyridine)
- 3,5-Lutidine (3,5-dimethylpyridine)
| Lutidines | ||||||
| Name | 2,3-Lutidine | 2,4-Lutidine | 2,5-Lutidine | 2,6-Lutidine | 3,4-Lutidine | 3,5-Lutidine |
| Systematic Name | 2,3-Dimethylpyridine | 2,4-Dimethylpyridine | 2,5-Dimethylpyridine | 2,6-Dimethylpyridine | 3,4-Dimethylpyridine | 3,5-Dimethylpyridine |
| Structural formula |  |
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| CAS Registry Number | 583-61-9 | 108-47-4 | 589-93-5 | 108-48-5 | 583-58-4 | 591-22-0 |
All isomers share the molecular weight 107,16 g/mol and the chemical formula C7H9N.
Applications
[edit]- 3,4-Lutidine [583-58-4] has formal application in the synthesis of a large bevy of benzomorphan opioid analgesics including: Metazocine, Phenazocine, Ketazocine, Pentazocine, Tonazocine, Volazocine, Cyclazocine, Alazocine, 8-Carboxamidocyclazocine, Fluorophen, Quadazocine, ID-1229, LP-1,[2] MR-2034 [57236-85-8].
- 2,3-Lutidine [583-61-9] has application in the synthesis of Rabeprazole, Lansoprazole, Ilaprazole
References
[edit]- ↑ Anderson, Thomas (1851-04-21). "On the Products of the Destructive Distillation of Animal Substances. Part II". Transactions of the Royal Society of Edinburgh. 20 (2) (published 1853): 247–260. doi:10.1017/S0080456800033160. ISSN 2053-5945.
- ↑ Parenti C, Turnaturi R, Aricò G, Marrazzo A, Prezzavento O, Ronsisvalle S, Scoto GM, Ronsisvalle G, Pasquinucci L. Antinociceptive profile of LP1, a non-peptide multitarget opioid ligand. Life Sci. 2012 Jun 27;90(25-26):957-61. doi: 10.1016/j.lfs.2012.04.041. Epub 2012 May 11. PMID: 22580287.
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