[eduardo.vignon]

Hello all:

I was having a discussion with a friend this afternoon and I was wondering if anyone could help me out. My question is: Is amphetamine an acid??
The whole discussion began because I said that the pH may be acid but that does not makes the chemical compound of amphetamine an acid.  Am I right? I would like some help here, we made a bet

Cheers to all

Eduardo

[sjb]

Is amphetamine an acid??

What do you understand an acid to be? There are various definitions, depending on exactly what sort of work you're doing.

S

[ATMyller]

Amphetamine has an amine group (-NH₂) which is amphoteric meaning it can function as both acid or base depending on the situation. Other functional groups like alcohols and thiols have similar properties. So amphetamine can be (weakly) acidic, but defintely not an acid.

[AWK]

Amphetamine has an amine group (-NH₂) which is amphoteric meaning it can function as both acid or base depending on the situation. Other functional groups like alcohols and thiols have similar properties. So amphetamine can be (weakly) acidic, but defintely not an acid.

I disagree. An amino group is much much more basic than an alcohol acidic Moreover, amphetamine itself do not contain other basic or acidic groups.
Real pH of drug is another goals of wool.

[profmsg]

Amphetamine has an amine group (-NH₂) which is amphoteric meaning it can function as both acid or base depending on the situation. Other functional groups like alcohols and thiols have similar properties. So amphetamine can be (weakly) acidic, but defintely not an acid.

I disagree. An amino group is much much more basic than an alcohol acidic Moreover, amphetamine itself do not contain other basic or acidic groups.
Real pH of drug is another goals of wool.

amine in acetaminophen is aromatic amine as NH2 is joined with benzene..
Aromatic amines have the nitrogen atom connected to an aromatic ring as in anilines. The aromatic ring strongly decreases the basicity of the amine, depending on its substituents. Interestingly, the presence of an amine group strongly increases the reactivity of the aromatic ring, due to an electron-donating effect. One organic reaction involving aromatic amines is the Goldberg reaction.

[Borek]

amine in acetaminophen is aromatic amine as NH2 is joined with benzene.

It is separated from the aromatic ring by three aliphatic carbons, I am not sure it still counts as "aromatic amine".

[AWK]

[Wikipedia shows structure od amphetamine.

It is separated from the aromatic ring by three aliphatic carbons, I am not sure it still counts as "aromatic amine".

It is evidently benzylamine derivative, not aniline derivative. It has an amino group separated by one aliphatic carbon from phenyl ring.

amine in acetaminophen is aromatic amine as NH2 is joined with benzene..
Aromatic amines have the nitrogen atom connected to an aromatic ring as in anilines. The aromatic ring strongly decreases the basicity of the amine, depending on its substituents. Interestingly, the presence of an amine group strongly increases the reactivity of the aromatic ring, due to an electron-donating effect. One organic reaction involving aromatic amines is the Goldberg reaction.

Acetaminophen and amphetamine are completely different compounds. Of course phenyl ring of amphetamine shows a small influence on basicity of amine but only through an inductive effect and inversely, an alkyl group change reactivity of phenyl ring.

[Borek]

Sorry, I have miseed this amphetamine -> acetaminophen teleportation, I was thinking about the original compound all the time.