What exactly makes a Tryptamine a Tryptamine

[N0ly]

i have enough confedence that i have searched the forum for the simplest answer and the question is never asked directly. so what makes a Tryptamine a Tryptamine and sepatrates them from the rest of the RC's. I have a basic knowledge of biochemistry so try to go into detail. Thank you in advance.

[StigmataLectron]

A tryptamine is a chemical that has the basic skeleton of the chemical "Tryptamine". Same with Phenethylamine.

[quote]trypt-amine \ 'trip-ta-,men \ n. [tryptophan fr. tryptic, fr. trypsin, fr. Gk. tryein, to wear down (from its occurence in pancreatic juice as a proteolytic enzyme) + amine fr. NL ammonia] 1: A naturally occurring compound found in both the animal and plant kingdoms. It is an endogenous component of the human brain. 2: Any of a series of compounds containing the tryptamine skeleton, and modified by chemical constituents at appropriate positions in the molecule.

[radiometer]

The attached picture is tryptamine. The two ring-shaped parts are the "trypt" and the tail on the right is the "amine." Another name for these compounds is "indoles." Any drugs which are based on this molecular structure are called "substituted tryptamines," or just "tryptamines" for short.

Reputation Comments on this post:

[Alfa]

I was under the impression the two ring shaped parts (six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring) is the indole and the tail on the right makes the indole a tryptamine as well. Tryptamine is 3-(2-Aminoethyl)-indole.

[Nagognog2]

Yes. The "tail" is R-ethylamine with R = Benzopyrole = indole. Carbon 3 is where the ethylamine is attached. Removing the H2 from the NH2 on the ethylamine and replacing them with methyl - CH3 - results in n,n-dimethyltryptamine: DMT.

There will be a test tomorrow...

[Alfa]

So, that makes DMT 3-(2-methylamine)-indole?

[ChemicallyBound]

Would not 3-(2-methylamine)-indole be Methyl tryptamine? or mono methyltyrtamine? Instead of Di methyl tryttamine , DMT?

[Nagognog2]

n-methyltryptamine, or mono-methyltryptamine (MMT) occurs in nature alongside both n,n-dimethyltryptamine and 5-methoxy-n,n-dimethyltryptamine. It apparently has none of the physiological actions of it's better known relatives.

[JewishNazi]

Originally Posted by Alfa

So, that makes DMT 3-(2-methylamine)-indole?

not quite Alfa, DMT is 3-[2-(dimethylamino)ethyl]indole

You need to specifyl the the methylamino group being attatched to the ethyl chain, and then that lot attatched to the indole

[Alfa]

Thanks, that makes it clear: Indole + Ethyl chain(tail) + dimethylamino. I didn't visualise it right. Should have looked the structure up.
DMT:

[pharmapsyche]

Tryptamine is a monoamine compound that is widespread in nature. Biosynthese generally proceeds from the amino acid tryptophan, with tryptamine in turn acting as a precursor for other compounds including indole, beta-carboline and ergoline alkaloids and auxins. Substitutions to the trypamine molecule give rise to a group of compounds collectively known as tryptamines. Tryptamine alkaloids found in fungi, plants and animals are commonly used by humans for there psychotropic effects. Prominent examples include psilcybin and DMT (as you guys were already talking about above). The tryptamine backbone can also be identified as part of the structure of some more complex compounds, such as...ergoline alkaloids, LSD, ibogaine, and yoimbine.
Also, if you check out the book TIHKAL, you'll learn alot!

Reputation Comments on this post:

[JewishNazi]

and strangely engough alot of alkaloids found in sea creatures and plants have bromine substitutions, a very rare element in the ocean

[hazeinmybong2]

Tryptamines are like AMT, 5-meo-AMT, DiPT, DMT, 4-HO-DMT(psilocybin).
I have read that if you give mushroom substrate a tryptamine it will hydroxylize it. So you give it DiPT, you get mushrooms with 4-HO-DiPT.

Most RCs that are available now are phenethylamines like any 2c-x. Mescaline is the only natural one I know but peyote probably makes like 20 others.

[treefingers49]

There are many many many natural phenethylamines. The phenethylamine skeleton is a very simple and common structure. as with the tryptamine model. Most phenethylamines and tryptamines are not psychoactive.

[Silence_Inc]

do all tryptamines give mind/sense-altering affects on the brain?


(btw - i'm a nobody when it comes to chemistry but i find it highly interesting)

[Alfa]

No, they don't. Melatonine works great as a sleep and jetlag aid. Asides that it makes you sleepy and drowsy, it's not psychoactive.

[daeron]

a tryptamine is what you get when a overzelous scientist thinks its up to him to name a compound, thinking that iupac aint enough.

well sometimes its a good thing sometimes a bad, one-like in this thread.

a tryptamine is a trivial name for a certain structure, and having in mind that most of the scientists are really just lazy bums, it was readly accepted as a class of compounds by itself. and it makes the research of the supsituted analogues easier, since its is easier to say N,N dimethyl tryptamine than 3-(2-(N,N dimethylamino)ethyl) indole, now innit?

and thats not mentioning how indole was called before the name was accepted, lol. chemistry is often retarded like that, but i dare yous to find a better way!-No, "stuff" aint a valid nomenclature term

[radiometer]

What is the derivation/explanation of the word tryptamine? Phenethylamine is clear to me, but not tryptamine.

[daeron]

as the man himself says:

trypt-amine \ 'trip-ta-,men \ n. [tryptophan fr. tryptic, fr. trypsin, fr. Gk. tryein, to
wear down (from its occurence in pancreatic juice as a proteolytic enzyme) + amine
fr. NL ammonia] 1: A naturally occurring compound found in both the animal and
plant kingdoms. It is an endogenous component of the human brain. 2: Any of a
series of compounds containing the tryptamine skeleton, and modified by chemical
constituents at appropriate positions in the molecule.

IMO just an another trivial bullshit,lol

(trivial as in nomenclature, dont get me wrong)

[hazeinmybong2]

Would a rose smell as sweet called by any other name?

[radiometer]

Originally Posted by Alfa

I was under the impression the two ring shaped parts (six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring) is the indole and the tail on the right makes the indole a tryptamine as well. Tryptamine is 3-(2-Aminoethyl)-indole.

Thanks alfa and J_N for noting that distinction, I knew I was bound to cock something up in my explanation.

[raven3davis]

Originally Posted by radiometer

What is the derivation/explanation of the word tryptamine? Phenethylamine is clear to me, but not tryptamine.

]

SWIM wonders this too. Do you think the word tripping is derived from the word tryptamine?

[JewishNazi]

Originally Posted by raven3davis

]

SWIM wonders this too. Do you think the word tripping is derived from the word tryptamine?

No, I beleive it is called such because people feel asthough they have been on an adventure, or trip, from reality

[Nagognog2]

Yes. And a tryptophan is a person whose brain has a case of the farts like a breeze being blown out their ears - and they enjoy it.

[grandbaby]

Ooh, trypto-fans. LOL.

And then there are the phenethylamorists....