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Cantharidin AI simulator
(@Cantharidin_simulator)
Hub AI
Cantharidin AI simulator
(@Cantharidin_simulator)
Cantharidin
Cantharidin is an odorless, colorless fatty substance of the terpenoid class, which is secreted by many species of blister beetles. Its main current use in pharmacology is treating molluscum contagiosum and warts topically. It is a burn agent, poisonous in large doses. It has been historically used as an aphrodisiac (in potions sold under the name "Spanish fly"). In its natural form, cantharidin is secreted by the male blister beetle, and given to the female as a copulatory gift during mating. Afterwards, the female beetle covers her eggs with it as a defense against predators.
Poisoning from cantharidin is a significant veterinary concern, especially in horses, but it can also be poisonous to humans if taken internally (where the source is usually experimental self-exposure). Externally, cantharidin is a potent vesicant (blistering agent), exposure to which can cause severe chemical burns. Properly dosed and applied, the same properties have also been used therapeutically, for instance, for treatment of skin conditions, such as molluscum contagiosum infection of the skin.
Cantharidin is classified as an extremely hazardous substance in the United States, and is subject to strict reporting requirements by facilities that produce, store, or use it in significant quantities.
Cantharidin, from the Greek kantharis, for beetle, is an odorless, colorless natural product with solubility in various organic solvents,[specify] but only slight solubility in water. Its skeleton is tricyclic, formally, a tricyclo-[5.2.1.02,6]decane skeleton. Its functionalities include a carboxylic acid anhydride (−CO−O−CO−) substructure in one of its rings, as well as a bridging ether in its bicyclic ring system.
The level of cantharidin in blister beetles can be quite variable. Among blister beetles of the genus Epicauta in Colorado, E. pennsylvanica contains about 0.2 mg, E. maculata contains 0.7 mg, and E. immaculata contains 4.8 mg per beetle; males also contain higher levels than females.
Males of Berberomeloe majalis have higher level of cantharidin per beetle: 64.22 ± 51.28 mg/g (dry weight) and 9.10 ± 12.64 mg/g (d. w.). Cantharidin content in haemolymph is also higher in males (80.9 ± 106.5 μg/g) than in females (20.0 ± 41.5 μg/g).
There have been multiple synthetic approaches to achieve cantharidin in the lab. A common strategy employed by different total synthesis methods is to begin with a Diels-Alder cycloaddition reaction to form the six-membered ring. The starting material often utilizes a furan as the diene, giving the formation of a bicyclic ring.
The complete mechanism of the biosynthesis of cantharidin is unknown. Its framework formally consists of two isoprene units. However, feeding studies indicate that the biosynthetic process is more complicated, and not a simple product of geranyl pyrophosphate or related ten-carbon parent structure, as the seeming monoterpene nature would suggest. Instead, there is a farnesol (15-carbon) precursor from which certain carbon segments are later excised.
Cantharidin
Cantharidin is an odorless, colorless fatty substance of the terpenoid class, which is secreted by many species of blister beetles. Its main current use in pharmacology is treating molluscum contagiosum and warts topically. It is a burn agent, poisonous in large doses. It has been historically used as an aphrodisiac (in potions sold under the name "Spanish fly"). In its natural form, cantharidin is secreted by the male blister beetle, and given to the female as a copulatory gift during mating. Afterwards, the female beetle covers her eggs with it as a defense against predators.
Poisoning from cantharidin is a significant veterinary concern, especially in horses, but it can also be poisonous to humans if taken internally (where the source is usually experimental self-exposure). Externally, cantharidin is a potent vesicant (blistering agent), exposure to which can cause severe chemical burns. Properly dosed and applied, the same properties have also been used therapeutically, for instance, for treatment of skin conditions, such as molluscum contagiosum infection of the skin.
Cantharidin is classified as an extremely hazardous substance in the United States, and is subject to strict reporting requirements by facilities that produce, store, or use it in significant quantities.
Cantharidin, from the Greek kantharis, for beetle, is an odorless, colorless natural product with solubility in various organic solvents,[specify] but only slight solubility in water. Its skeleton is tricyclic, formally, a tricyclo-[5.2.1.02,6]decane skeleton. Its functionalities include a carboxylic acid anhydride (−CO−O−CO−) substructure in one of its rings, as well as a bridging ether in its bicyclic ring system.
The level of cantharidin in blister beetles can be quite variable. Among blister beetles of the genus Epicauta in Colorado, E. pennsylvanica contains about 0.2 mg, E. maculata contains 0.7 mg, and E. immaculata contains 4.8 mg per beetle; males also contain higher levels than females.
Males of Berberomeloe majalis have higher level of cantharidin per beetle: 64.22 ± 51.28 mg/g (dry weight) and 9.10 ± 12.64 mg/g (d. w.). Cantharidin content in haemolymph is also higher in males (80.9 ± 106.5 μg/g) than in females (20.0 ± 41.5 μg/g).
There have been multiple synthetic approaches to achieve cantharidin in the lab. A common strategy employed by different total synthesis methods is to begin with a Diels-Alder cycloaddition reaction to form the six-membered ring. The starting material often utilizes a furan as the diene, giving the formation of a bicyclic ring.
The complete mechanism of the biosynthesis of cantharidin is unknown. Its framework formally consists of two isoprene units. However, feeding studies indicate that the biosynthetic process is more complicated, and not a simple product of geranyl pyrophosphate or related ten-carbon parent structure, as the seeming monoterpene nature would suggest. Instead, there is a farnesol (15-carbon) precursor from which certain carbon segments are later excised.
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