IUPAC dilemma on naming a toxin, any pro organic chemists out there?

In summary, a compound called Batrachotoxinin A has been identified and its IUPAC name was previously unknown. After further research, it was found that Batrachotoxinin A is a relative of Batrachotoxin, which has a specific IUPAC name. However, Batrachotoxinin A has a different chemical structure and cannot be named in the same way. After some investigation, the IUPAC name for Batrachotoxinin A has been determined to be [5\alphaR-[5\alpha\alpha,7\alpha\beta,9\alpha,11\alpha\beta,11\beta\alpha,12\alpha,13\alpha\alpha,
  • #1
Whakataku
12
0
So I came across a cool toxin, and saw that people have not assigned an IUPAC name to it, so I took on the challenge.

The compound of interest is Batrachotoxinin A

unc.
edu/depts/mtcgroup/litmeetings/batrachotoxinin.pdf

In the second slide Batrachotoxinin A has an R which is an H instead of a pyrolle moiety.

Now Batrachotoxinin A's relative Batrachotoxin (the one with the pyrolle moiety) has the following IUPAC name

1H-Pyrrole-3-carboxylic acid, 2,4-dimethyl-, (1S)-1-[(5aR, 7aR, 9R, 11aS, 11bS, 12R, 13aR)-1,2,3,4,7a,8,9,10,11,11a , 12,13- dodecahydro-9,12-dihydroxy-2, 11a-dimethyl- 7H-9,11b-epoxy-13a, 5a-propenophenanthro[2,1-f] [1,4] oxazepin-14-yl] ethyl ester


So is the Batrachotoxinin A's IUPAC
(1S)-1-[(5aR, 7aR, 9R, 11aS, 11bS, 12R, 13aR)-1,2,3,4,7a,8,9,10,11,11a , 12,13- dodecahydro-9,12-dihydroxy-2, 11a-dimethyl- 7H-9,11b-epoxy-13a, 5a-propenophenanthro[2,1-f] [1,4] oxazepin-14-yl] ethyl ester

(As you can see I just deleted 1H-Pyrrole-3-carboxylic acid, 2,4-dimethyl-,)

is that ok?
 
Chemistry news on Phys.org
  • #2
Wait I take that Batrachotoxinin A does not have carboxylic acid any more, but a hydroxy group, so it's not an ester, but an alcohol.

So I somehow have to name it with a substituted ethanol??

Any hints??
 
  • #3
Never mind, I found the name:

[5[itex]\alpha[/itex]R-[5[itex]\alpha[/itex][itex]\alpha[/itex],7[itex]\alpha[/itex][itex]\beta[/itex],9[itex]\alpha[/itex],11[itex]\alpha[/itex][itex]\beta[/itex],11[itex]\beta[/itex][itex]\alpha[/itex],12[itex]\alpha[/itex],13[itex]\alpha[/itex][itex]\alpha[/itex],14(S*)]]-1,2,3,4,7a,10,11,11[itex]\alpha[/itex],12,13-Decahydro-14-(1-hydroxyethyl)-2,11[itex]\alpha[/itex]-dimethyl-7H-9,11[itex]\beta[/itex]-epoxy-13[itex]\alpha[/itex],5[itex]\alpha[/itex]-propenophenanthro[2,1-f][1,4]oxazepine-9,12(8H)-diol
 

1. What is the IUPAC dilemma on naming a toxin?

The IUPAC (International Union of Pure and Applied Chemistry) dilemma on naming a toxin refers to the challenges faced by organic chemists in naming toxins, which are complex chemical compounds that can have harmful effects on living organisms.

2. Why is naming a toxin difficult for organic chemists?

Naming a toxin is difficult for organic chemists because toxins often have complex molecular structures and can contain multiple functional groups, making it challenging to follow the traditional rules of IUPAC nomenclature.

3. How does the IUPAC suggest naming toxins?

The IUPAC suggests using systematic names for toxins, which involve breaking down the molecular structure into smaller parts and naming each part individually according to the traditional IUPAC rules.

4. What are some of the challenges in using systematic names for toxins?

Some of the challenges in using systematic names for toxins include the length and complexity of the names, as well as the potential for errors in naming due to the large number of functional groups and possible variations in the molecular structure of toxins.

5. Are there any alternative methods for naming toxins?

Yes, there are alternative methods for naming toxins, such as using trivial names or common names that are not based on the molecular structure but are easier to remember and use in everyday language. However, these names may not accurately reflect the chemical composition of the toxin and can lead to confusion and inconsistencies in scientific literature.

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