[mbracha]

I'm a medical student, after a pretty hard exam. I'm trying to find a "case" to cancel one of the questions in the test. We were asked to circle the ormone that is not amine-hormone. I choose Melatonin, while the right answer is Melamine.

I need your briliant help to give me a case for claiming that melatonin isn't a amine (maybe in one stage of it's synthesis) or that melamine is amine, or some kind of amine derivates.

I know it's a long shot, but i'm sure there are some genius minds here that can twist it for me.

Have a great day.

[enahs]

Melamine has multiple amine functional groups in it. It is an amine.

Melatonin has both a cyclic amine and a amide functional group in it. It is technically both.

However, melatonin however is a bicyclic amine, turning it into the indol functional group according to the IUPAC. Therefor technically by nomenclature from the IUPAC, melatonin is an amide and an indol. Indols have of course many similarities to amines.

It is not a twist. That is what it is. It is a stupid question in the first place.

[Åke]

enahs, indole is not really an amine it has more of an enamine character e.g. it is not basic and it reacts with electrophiles mostly at carbon (C-3).

mbracha, as far as I know melamine is not a hormone so how can melamine be the correct answer? Melatonin is a hormone with two nitrogen-containing functional groups: an amide and an enamine.

[mbracha]

First, thank you both for responding. My Biochemistry professor is a total jerk, so I'm not that suprised. Do you have any strong references to prove that Melatonin couldn't be classified as an amine? If i want to get these critical points i need strong facts to back me up.

And again, thank you all, you give me a lot of hope.

[enahs]

How about that its IUPAC name is N-[2-(5-methoxy-1H-indol-3-yl)ethyl]ethanamide

See where it says amide and not amine?

[mbracha]

Do you have a link to that? in wikipedia (don't kill me for using it) it states the same name but with "amine" instead of "amide" in the end.

[Åke]

Amide functional group is at the core of biochemistry, I find it hard to believe that a biochemistry professor is not familiar with it. That said, here are the links:

Amide: http://en.wikipedia.org/wiki/Amide

Amine: http://en.wikipedia.org/wiki/Amine

[mbracha]

I meant that in "melatonin" page on wikipedia they call it amine, not amide. I need an approved site that states clearly that melatonin is an amide and not amine.

[Fluorine]

Mbracha, on wikipedia it does mention 'amine' in the alternative name "N-acetyl-5-methoxytryptamine" however that is going off a 'shorthand' naming not IUPAC based. In other words what it's saying is the parent is tryptamine and not indole. The reason for this is it's a lot easier than writing out the IUPAC name, N-[2-(5-methoxy-1H-indol-3-yl)ethyl]ethanamide as Enahs mentioned, every time in your paper.

In this case it was named through an amine, tryptamine, however the actual molecule itself is not an amine, rather amide. You could try convincing your instructor otherwise but you might be hard-pressed if you are not fully grasping the difference and why melatonin is not an amine.

[Honclbrif]

Maybe you should consider being a lawyer instead of a doctor...

[fledarmus]

I think you're stuck arguing the wrong side of the name, "amine-hormone". As far as I can tell, melamine is not a hormone at all. I haven't been able to find a natural source for the compound, and the only references I have seen to melamine in food is as an adulterant, and in organisms is as a metabolite of synthetic drugs.

As I understand it, there are basically three types of hormones - amine hormones, which are derived from single amino acids; peptide hormones, which are chains of amino acids linked by amide bonds; and steroid hormones which have the quadricyclic structure of cholesterol. Although it doesn't actually have a free amine, melatonin is classified as an amine hormone due to the fact that it is a simple derivative of a single amino acid, tryptophan.

It would be hard to argue with your professor given this list:

http://en.wikipedia.org/wiki/List_of_human_hormones

[Åke]

fledarmus, that's interesting - I wasn't aware of that nomenclature.

[typhoon2028]

I guess I see what you are trying to accomplish; you trying to improve your score on a test through a technicality.

I think you lost sight of the goal of a test.