Baeocystin is a hallucinogenic compound that is isolated from the mushroom Psilocybe baeocystis and has the structure shown below. What heterocyclic base (Table 16.1) is the parent of this compound?

Question

Chemical structure of Baeocystin, a hallucinogenic compound from Psilocybe baeocystis, labeled with its components.

Accepted Answer

All right. Hi, everyone. So this question says that nn dimethyltryptamine is a hallucinogenic substance that is a psychedelic drug prepared by various cul cultures. For ritual purposes identify the heterocyclic amine. That is the parent of this compound. Option. A says imidazole. Option B says Peridin option C says purine and option D says Indo. So recall first and foremost that in the context of organic chemistry, we can refer to hetero Adams. Now hero Adams are essentially any adam other than carbon or hydrogen. So nitrogen, oxygen fluorine etc are all examples of hetero atoms. So we can refer to a heterocyclic compound as a ring structure or a cyclic compound containing these hetero atoms as part of the ring itself. So the ring would contain carbon atoms but also hetero atoms like oxygen or nitrogen, for example. So in the case of this question, where we are looking for a heterocyclic amine, the ring should be composed of carbon and nitrogen. So nitrogen would be the hetero atom in the ring. So in this case, our only task is to go ahead and locate the structure in this molecule in nn dimethyltryptamine that contains a ring with nitrogen as part of the ring itself. And if I consider the top part of my structure here, I can see exactly where that heterocyclic ring or heterocyclic part of the molecule happens to be. Now, I want to point out here that I actually went ahead and circled both of the rings that are fused together, one of which contains nitrogen. And the reason why I did this is because notice how both rings are not only fused together, but they also have a conjugated pi electron system. Because notice how we have all these double bonds that are separated by one single bond in between them. That is what I refer to when I describe a conjugated system and that is characteristic of aromatic compounds. So in this case, right, due to the conjugated pie system, this specific part of the molecule is of course cyclic, but it is also plainer due to the geometry of this pi system, it is fully conjugated as I discussed previously because nitrogen, if you recall also has a lone pair of electrons that can participate in the pie system, right. So it is also conjugated. And if I count the total number of pi electrons eight from my four pi bonds and two from by nitrogen atom, I get a total of 10 pi electrons in my conjugated system. So according to Hackle's rule, if I were to solve for the expression for an attitude two equals 10, then M would give me a whole number. Therefore, the conjugated system being shown here does obey Hackle's rule and is therefore considered aromatic. Now, because the whole system is considered aromatic, they can be grouped together even though there are two separate rings, not two separate rings, but two rings. So of the four heterocyclic amines proposed here, recalled imidazole and pirolli are both hetero cycles that contain only one ring structure. So I'm going to go ahead and eliminate them both. But we call it purine. Well, purine looks very similar to the structure we are given in that there are two fused rings, right, one of which contains six atoms and the other contains five atoms. But I want to point out some of the differences in its structure right now, I'm drawing puri right on the right side of the screen is purine. Now notice how purine it is a heterocycosis atoms in the ring system, whereas the compound shown only contains one nitrogen as part of the ring structure. So therefore, purine is disqualified and our final answer is going to be option D because it is in fact indo and there you have it. So with that being said, thank you so very much for watching and I hope you found this helpful.

Baeocystin is a hallucinogenic compound that is isolated from the mushroom Psilocybe baeocystis and has the structure shown below. What heterocyclic base (Table 16.1) is the parent of this compound?

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Key Concepts

Heterocyclic Compounds

Psilocybe baeocystis

Baeocystin