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Batrachotoxin

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Batrachotoxin
Batrachotoxin.png
General
Other names BTX
Molecular formula C31 H42 N2 O6
Molar mass 538.68 g·mol−1
Appearance Clear liquid
CAS number 23509-16-2
Properties
Density 1.304 g/mL
Solubility in lipid DMSO
Boiling point 744.0°C
Acidity (pKa) 7.87 +/- 0.70
Hazards
MSDS Material safety data sheet
Main hazards highly toxic, fatal if swallowed
NFPA 704

NFPA 704 svg.png

1
2
0
OX
Flash point 403.8°C
RTECS number CR3990000
Related compounds
Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Disclaimer and references

When you think of the poison dart frog you think cute colorful frog. I think then you remember most animals and insects that are very colorful are a warning a red flag if you will to the other animals in the jungle and humans alike. It says I look amazing and tasty, but I will kill you. The poison dart frog is no different as he has the ability to kill up to ten men. The poison dart frog gets his poison from insects proving again you are what you eat. As with anything in nature there is always a way to reverse engineer it and make it for your own uses. The poison from the dart frog is no different. It can be created in a lab and has been since 1998 when it was discovered it could be replicated and used for testing on humans to see how our nerves conduct electricity. The good news is people are beginning to use it for positive learning experiences, the bad news is there is no known cure at this time if you are accidentally exposed.

Properties

Chemical

Batrachotoxin is one of the most toxic of the four steroidal alkaloids and is extracted from the Columbian arrow poison frog [1]. Three other steroidal alkaloids are present: iso-BTX, pseudo-BTX, and BTX-A. BTX is one of the most potent and specific activators of sodium channels [1]. BTX changes the activation and inactivation of sodium channels leaving them to remain open at a resting membrane potential, which increases the resting sodium permeability [1]. BTX binds to the same receptor as several other lipid-solution neurotoxins, but BTX is distinct from that of tetrodotoxin. The damage done to the membrane sodium permeability is irreversible. BTX has no effect to normal skin, but if it comes in contact with an open wound it will cause long lasting pain. If digested or entering through an abrasion BTX blocks neuromuscular transmission and causes muscular contractions. BTX goes on to cause muscular contracture leading to respiratory paralysis and death [1]

Physical

The physical properties include the fact it is considered a solid. It can be seen as a crystalline white powder.

Synthesis

One of the many uses include hunting

Before 1998, it was thought that Batrachotoxins were so complex that they could not be synthesized in the laboratory. Batrachotoxin, at that time, had only been partially synthesized from batrachotoxinin A. However, in 1998, Kurosu et al reported that they had synthesized (+/-)-Batrachotoxinin A from (+/-)-cis-decalone; this synthesis can be considered a "formal total synthesis" of (+/-)-Batrachotoxin since batrachotoxinin A can be converted into Batrachotoxin (13). Important steps in this synthesis include an intramolecular furan Diels-Alder reaction to construct the steroid skeleton, and an intramolecular oxy-Michael reaction to synthesize the oxazapane ring. In general, the Diels-Alder reaction is used to form six-membered rings such as those present in steroid skeletons and the Michael reaction uses carbonyl compounds as reactants (these carbonyl compounds are intermediates and reagents involved in the synthesis of batrachotoxin).. [2]

Uses

One of the frogs used to make the hunters poison darts

This poison has many uses it seems, one is by the indigenous people of Columbia's lower rain forest. Scientists have discovered how to recreate the poison in 24 easy steps.[3]. Du Bois and his colleagues have figured out this makes a wonderful way to see how nervous use electricity [3]. Once inside an individual, the poison embeds itself in certain proteins that are responsible for conducting electrical impulses through the nerves and muscles, one of which is the the heart. By disrupting that process, it can cause paralysis and a heart attack. But studying the poison's mode of action could also lead to a deeper understanding of the role electrical impulses play in fundamental processes like heart function and the sensation of pain, [3]. Du Bois says there are very few molecules that work on this level and we would like to understand them more [3]. De Bois is hoping his findings will lead to a usefulness of this drug. One of the disorders this can help them with makes it so a person ca not feel pain at all. These people can literally have a knife edge drawn through their hand and not feel a thing [3]. They hope to find a usefulness of ratios drug similar to what happened with curare. A nasty poison from plants that is now used in a lower lever for pain relief during surgeries. [3]. That all being said it does not currently have many uses, but the team hopes to find new uses for Batrachotxin, in the way of medicine.

Video

Poison darts prove you were what you eat!

References

  1. 1.0 1.1 1.2 1.3 Hodgson, Ernest [1] "science direct". Web March 19, 2018. (accessed)
  2. Grimes Holy. [2] 'UK School". March 20, 2018 (accessed)
  3. 3.0 3.1 3.2 3.3 3.4 3.5 Bichell, Rae Ellen. [3] "National Public Radio". March 20, 2018 (accessed)