Amino Alkaloids

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Chapter: Pharmacognosy and Phytochemistry : Drugs Containing Alkaloids

One or more carbon rings with a nitrogen atom on a carbon side chain. One of the most interesting alkaloids in this group is mescaline from Lophophora williamsii. Mescaline has a molecular structure that is remarkably similar to the brain neurotransmitter dopamine. It is also structurally similar to the neurohormone norepinephrine (noradrenalin) and to the stimulant amphetamine. In the peyote cactus, mescaline is formed in a complex pathway from the amino acid tyrosine.


AMINO ALKALOIDS

 

 

One or more carbon rings with a nitrogen atom on a carbon side chain. One of the most interesting alkaloids in this group is mescaline from Lophophora williamsii. Mescaline has a molecular structure that is remarkably similar to the brain neurotransmitter dopamine. It is also structurally similar to the neurohormone norepinephrine (noradrenalin) and to the stimulant amphetamine. In the peyote cactus, mescaline is formed in a complex pathway from the amino acid tyrosine. A similar pathway in humans produces epinephrine (adrenalin) and its demethylated precursor norepinephrine from tyrosine. Dopamine and its precursor L-dopa are also derived from a tyrosine pathway, Mescaline also occurs in several other cactus species, including the commonly cultivated, night-blooming, South American San Pedro cactus (Trichocereus pachanoi).

 

Another alkaloid called ephedrine has a molecular structure similar to that of mescaline. Since ephedrine has a chemical structure similar to epinephrine (adrenalin), it works like a powerful cardiac stimulant that may cause cardiac arrest in infants and heart patients. New synthetic drugs based on the ephedrine/epinephrine ring structure are now marketed as effective and safer bronchodilators. Pseudoephedrine, an isomer of ephedrine, also occurs in species of Ephedra, and may be produced synthetically. Compared to ephedrine, it causes fewer heart symptoms, such as palpitation, but is equally effective as a bronchodilator.

 

Colchicine is a 3-ring amine alkaloid derived from the corms of Colchicum autumnale, a member of the lily family (Liliaceae). Like the anticancer indole alkaloids, vinblastine and vincristine, it is a spindle poison causing depolymerization of mitotic spindles into tubulin subunits. This effectively stops the tumor cells from dividing, thus causing remission of the cancer. It is a powerful inducer of polyploidy because it can stop plant cells from dividing after the chromatids have separated during anaphase of mitosis. It is used as a mutagen.

 

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