Mesitylene or 1,3,5-trimethylbenzene is a derivative of benzene with three methyl substituents positioned symmetrically around the ring. There are many reported cases of the toxic poisoning from mesitylene. It is also used as an insecticide, an anti-coagulant, a disinfectant, an anti-inflammatory agent and as a pesticide and it is quite harmful if ingested or absorbed through the skin. So, it is quite useful for medicinal chemistry although the therapeutic activity has not been established.
Mesitylene is derived from the Cinnamomum zeylanicum plant which is part of the cinnamomum family of volatile chemicals. It is a substituted aromatic hydroxy molecule having the basic structure of a benzene ring with one hydrogen atom in the outer shell and six carbon atoms at the center. Mesitylene is colorless, clear and odorless. It occurs in nature in large quantities as a component of coal tar, while the content diminishes during industrial processes. Mesitylene can be formed as a result of the reaction between an alkaline polarizing agent like sodium bromide and the amino acid L-Cysteine.
Mesitylene belongs to the aromatic class of compounds having a low solubility index and exhibit very low affinity for water and most insoluble fiber structures. Its organic base is believed to be Cinnamomum zeylanicum, the source of the sweet aromatic odor Mesitylene. Mesitylene is structurally similar to the trihalomethane molecule N-acetyl-dihydrotestosterone (DAHD), which was first isolated from a patient's adrenal glands. Mesitylene has similar structural features and uses the same oxidizing and reductant mechanisms. The similarity between the two substances lead researchers to conclude that Mesitylene is probably the precursor of DHA. DHA is the principal, essential amino acid in the nervous system and brain and makes important chemical reactions in cellular physiology and behavior.
Mesitylene has its advantages over DHA. Unlike DHA, which has a molecular size of less than one micrometer. This gives it the ability to become part of the lipid bilayer membranes in the nervous system. Because it has a high solubility index, mesitylene is able to easily dissolve in water and lipid soluble molecules such as fatty acids. Because it contains only one hydrogen atom, mesitylene is less expensive than other organic compounds in organic chemistry but more expensive in terms of toxicology exposure.
As mesitylene has only a single hydrogen atom, the compound is referred to as "halogen-free," which is useful for the purpose of food and drug identification. Another advantage of mesitylene over other organic compounds is that the compound has a rather low toxicity in animals and in man. Mesitylene has been found to be inactive in test tubes and is considered relatively safe. It is believed to be structurally similar to diphenylamine, the psychostimulant drug topically used for treatment of ADHD.
In comparison to the chemical composition of some commonly occurring street drugs like cocaine, ecstasy, methamphetamine, and marijuana, mesitylene is comparatively safe. Mesitylene lacks any of the psychostimulant or amphetamine characteristics and has been found to be effective in reducing appetite and reducing energy levels in laboratory animals. Comparisons have been made to the toxic compounds of amphetamines in animals. Mesitylene does not cause immediate death in laboratory animals; however, these tests are not conclusive because the effects may not occur in humans.
