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Gaz_hmmmm
28-01-2006, 19:44
Are there any caffeine related chem's that are recreational at all?

If not, would it be possible to play around with caffeine to make something pleasurable at all like amphetamine? :\

Jamshyd
28-01-2006, 20:54
The only thing remotely related to caffeine that I can think of that is recreational is fenethylline, and we can argue that this is closer to amphetamine than it is to caffeine. Caffeine works primarily through the adynosyl receptors, which don't seem to be too happy (or sad). Perhaps someone more knowledgeable can shed more light on it.

bigmac74
28-01-2006, 21:55
^^ What about theophylline and theobromine? They are pretty similar to caffeine, maybe not as recreational though.

Jamshyd
28-01-2006, 23:51
They are very similar to caffeine (I think theobromine feels the least horrible, and I find it somewhat sedating in some ways). I rarely drink highly caffinated drinks - generally only hot chocolate or occasionally tea. Caffeine actually feels bad for me.

J. Alfred Prufrock
29-01-2006, 01:51
Has fenethylline ever turned up in pill testing?

BilZ0r
29-01-2006, 02:53
I doubt it... I mean, adenosine ligands don't modulate conditioned place preference... well some people report they do[1 (http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=9251915&query_hl=9&itool=pubmed_docsum)], I'm not sure... but selective adenosine a1 antagonists might be a bit better [2 (http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=pubmed&dopt=Abstract&list_uids=12151508&query_hl=2&itool=pubmed_docsum)].

Jamshyd
29-01-2006, 03:20
Has fenethylline ever turned up in pill testing?

I do not think it exists in any mentionable quantities in North America.

This is supposedly popular in eastern europe and the middle east, though none of my acquaintances in either area have ever heard of it (to be fair, none of them are drug users).

In any case, apparently it is sold in pills as fenethylline or "captagon" in these areas (ie. not as "ecstasy").

What I wonder is whether it gets metabolized into Meth + Caffeine or Ethamphetamine + Theophyline? In both cases it would be interesting, since Ethamphetamine is rather rare and since pure Methamphetamine is almost unknown in these areas.

Katt
29-01-2006, 19:04
iirc, theophylline is highly toxic in doses higher than the therapeutical dose, which is additionally different in every single human being... so trying to use it for recreational purposes should be kind of dangerous.

Belisarius
29-01-2006, 19:49
I've heard that theobromine is much weaker than caffeine on a per-unit basis...

phase_dancer
30-01-2006, 02:25
Both theobromine and theophylline would be crap rec drugs IMO. However, fenethylline should be relatively easy to synthesize.

nuke
30-01-2006, 03:22
I do not think it exists in any mentionable quantities in North America.

This is supposedly popular in eastern europe and the middle east, though none of my acquaintances in either area have ever heard of it (to be fair, none of them are drug users).

In any case, apparently it is sold in pills as fenethylline or "captagon" in these areas (ie. not as "ecstasy").

What I wonder is whether it gets metabolized into Meth + Caffeine or Ethamphetamine + Theophyline? In both cases it would be interesting, since Ethamphetamine is rather rare and since pure Methamphetamine is almost unknown in these areas.

It's metabolised into amphetamine and theophylline: http://www.erowid.org/archive/rhodium/chemistry/shulgin.futuredrugs.html

I would be surprised if the psychopharmacological effects were discernable from amphetamine...

Jamshyd
30-01-2006, 06:43
It probably is no different from the amphetamine structure in it.

However, I am still puzzled, where do the two carbon atoms linking the two go if the end products are Amphetamine and Theophyline?

---

As for the topic at hand, for those who seem confused:

Cafeine: Is found at high concentration is Coffee and Kola nut.
Theopheline: Is found in tea at moderate concentrations, whith a lower concentration of caffeine.
Theobromine: Is found in chocolate (Theobroma cacao), along with smaller concentrations of Caffeine and Theophyline.
Yerba Mate contains high concentration of all three, I believe.

I could be wrong, of course.

morphiquet
07-02-2006, 22:10
there are several other purines that are closely related to caffeine, like pentofylline.
these are pure phosphodiesterase-inhibitors and show no activity to adenosin-receptors.
but don't ask me wether this does feel recreational in any way.

Xorkoth
10-02-2006, 19:20
If anyone discovers anything further about this fenethylline, please post. it sounds quite intriguing.

And I agree that the methylxanthines, especially caffeine, are crap. Very nasty, dirty stimulation.

hussness
10-02-2006, 20:51
anyone ever noticed that caffeine resembles uric acid (principle component of avian urine)? Maybe that's why it makes you feel like shit. ;)

BilZ0r
10-02-2006, 21:30
^ I suspect the phosphodiesterase inhibition is the nasty bit. Probably responsible for the shakes.

hussness
10-02-2006, 23:34
This is slightly off topic but the shakes/tremors that come with most sympathomimetic drugs -- what are they from?

BilZ0r
11-02-2006, 00:18
something to do with beta receptors in sympathomimetics; but I'm not convinced caffiene acts by the same mechanism.

Phat_bass49
11-02-2006, 15:56
I like to drink a coffee with a spliff if i have a heavy indica strain because it stops me from sleeping but doesn't ruin cannabis (like speed does)

jet-li
11-02-2006, 16:03
i know hydrocodone, like norco, or vicodins, contain caffeine. If you take enough of it before bedtime its hard to sleep. Stupid pharmys and their fillers.

BilZ0r
11-02-2006, 23:36
^ Um, it's for pain patients dude. The people who are supposed to be eating the vicodins, it's potentiates there analgesic action quite strongly.

BTB
24-02-2006, 22:30
"euphoric" properties of caffeine can be attributed to their indirect stimulation of dopaminergic neurons in the ventral tagmental area...which in turn will release dopamine in the nuclues accumbens.....thus suggesting its rewarding properties and addicitive properties

did you know the lethal dose of caffeine is 100 cups?.... I'll dig up the actually numeric value if anyone is interested

human
24-02-2006, 23:24
LD what? LD50? LD100? LD Low?
As I remember it, caffeine can be lethal to humans in a 4g dose. Assuming that a decently brewed cup of coffee is 120mg, that's only 33 cups. But like I said, I have no idea what measure of lethal dose you're referring to.

As an aside, is the increase in cAMP resultant from caffeine ingestion comparable to the decrease in cAMP (through adenylyl cyclase inhibition) resultant from opiates? I would think not, but I'm wrong all the time.

BilZ0r
24-02-2006, 23:37
I always figured it was a presynaptic action on dopaminergic terminals, but caffeine does increase unit activity in the VTA... though I wouldn't go so far as to say that it is dopamine release in the NAc that gives caffeine it's pleasant effect.. it has a serotonergic effect as well

BTB
24-02-2006, 23:58
I am sorry...I didnt mean to over-simplify it....

at the doses of average human consumption...the primary mechanism of action is actually the release of dopamine in the pre-frontal cortex.....must explain all the educated people sitting in my local cafe...

Smyth
25-02-2006, 00:14
There is this: http://www.guarana.com/

From what I can decipher its effects are very similar to caffeine.

I find it odd that your average Joe just thinks that tea/coffee/chocolate all contain caffeine. Whilst this may be true for coffee, I think I remember reading some place that very similar, yet not identical alkaloids exist in tea and chocolate. Yes Jamshyd also is aware of this little artifact.

I think this whole business is an interesting subject though.

Yeah looking at the structure of that 'Theophylline' alkaloid found in tea.

Although it contains three N-H groups, two of these are amides and so only one of these can be alkylated. Indeed, that Fenethylline is a masked amphetamine derivative.

There is a whole raft of other functional groups that could be attached to that nitrogen atom though. It seems inevitable that some exploration of the possibilities must have been attempted by some research body, either an academic or drug company at some stage.

J. Alfred Prufrock
25-02-2006, 19:32
This is a sample of guarana I picked up from a Japanese vendor a few years ago. Maybe it's worth an examination for actives, I always assumed it was just caffeine.

phase_dancer
26-02-2006, 03:18
Caffeine (CRC press)


The analysis of the methylxanthines (caffeine, theobromine, and theophylline) is important in the areas of nutrition and clinical chemistry.
These three compounds compose the majority of the alkaloids present in
coffee, tea, cocoa, cola nuts, and guarana.

The other mention regarding guarana:


Recently, Salvadori and colleagues published a study in which TLC was used as a screening tool for the determination of caffeine, theobromine, and theophylline in samples of horse urine after the horses had ingested guarana powder.


Salvadori, M.C., Rieser, E.M., Ribeiro Neto, L.M., and Nascimmento, E.S., Determination of xanthines by high performance liquid chromatography and thin layer chromatography in horse urine after ingestion of Guarana powder, Analyst, 119,2701,1994