Is 2ci and MAOI?

[fungus44]

There was some discussion of the low level MAOI activity of MDMA.

I've found 2ci to be a pretty effective potentiator of tryptamines. I've also had the usual quesiness in the gut that many other users have, not unlike some other MAOIs.

I realize that it's no something easily discovered due to the wide prohibition on psychedelic research, but do folks have any ideas or knowledge?

 

[BilZ0r]

I think it's very likely that it competes at MAO.
Breif research pulls up a newish paper from Dave Nichols, where if I'm not mistake compound 44 is 2CI and it reports an MAO-A IC50 of 43µM, but then there's no fucking way 2CI gets up to those kind of concentrations in recreational users.

Interestingly there are some thio- compounds (2CT) which have some serious IC50s ~100nM which are totally believable concs for those drugs to reach.

Still, assays are never perfect, and if that IC50 is out by a factor of 5, then that would be a serious MAOI.


[edit]Data 2nd references from Scorza, M. C.; Carrau, C.; Silveira, R.; Zapata-Torres, G.; Cassels,
B. K.; Reyes-Parada, M. Monoamine oxidase inhibitory properties
of some methoxylated and alkylthio amphetamine derivatives:
structure-activity relationships. Biochem. Pharmacol.
1997, 54, 1361-1369.[/edit]

 

[Blowmonkey]

Interestingly there are some thio- compounds (2CT) which have some serious ~100nM which are totally believable concs for those drugs to reach.

As in 2C-T-7? 2 of the T7 deaths were in combination with MDMA, but I guess it's still a bit farfetched to say that this was due to MAO inhibition from the 2C-T-7.

 

[specialspack]

What does IC50 mean wrt MAOs? And are the concentrations you mention plasma levels or in the brain (post-synaptic? is that what they're called?)

 

[BilZ0r]

IC50: Inhibitory Concentration to reach 50% inhibition.

i.e. the concentration of a chemical needed to get 50% inhibition of whatever effect. In this case it will be inhibition of the rate of degredation of a chemical which MAO-A or B is selective for breaking down.

 

[fastandbulbous]

Some of the 2C-T-x's are competetive inhibitors at physiokogical concentration. Might go part of the way towards explaining how the 2C-T-x's have been the ones implicated in most deaths concerning PEA's - competetive MAOI + serotonogic agent = serotonin syndrome. All the 2C-T-x related deaths (2 for 2C-T-7 & 1 for 2C-T-21) all seemed to implicate hyperthermia as the cause of death, which is the characteristic of serotonin syndrome

 

[yaesutom]

2C-T-21 at least to me, which is just subjective really, "feels" like it releases some serotonin or something but who knows.

 

[specialspack]

Interestingly there are some thio- compounds (2CT) which have some serious ~100nM which are totally believable concs for those drugs to reach.

How does this compare with other MAOIs?

Bit off topic, but how does AMTs supposed MAOI activity compare?

 

[BilZ0r]

IC50s don't really tell you a lot... I mean, another drug could have a much lower potency IC50, but so long as it is selective it could be a perfectly good drug. With drugs like this, the important thing is to compare the IC50 to the concentration the drug reaches in the body.

According to this paper AMT is a MAOI, but I don't have online access, so I dont know about it's potency

 

[fastandbulbous]

AMT is a competetive MAOI, but it's only marginally more potent than amphetamine. Harmaline is effective at 10^-6M, yohimbine at 10^-4 and AMT at 10^-2M, so although it is technically a MAOI, it doesn't have any effect at doses normally encountered in the human body

 

[fungus44]

Thanks all. On a related note: Do any of you know much about 2ci and its degradation? I understand it is unstable chemically. I've had a couple of experinces with a batch that has been passed around quite a bit without adulteration except for relatively clean utensils and/or fingers. The dose can go higher (25 or 30mg) and is more classically psychedelic a la a 1/2 g of mushrooms or low dose LSD than the relatively speedy feel of fresh 2ci.

Maybe it's placebo, but I don't think so.

 

[Morninggloryseed]

What leads you to believe 2C-I is unstable? I am not saying you are wrong, but everything I have learned and been told about 4-halo-2,5-DMPEAs and 4-halo-2,5-DMAs has led me to believe that whatever halogen is in that 4-position holds on tight to that benzene ring, and doesn't let go. I do know most simple amphetamines and many other substituted phenethylamines are very stable.

 

[fungus44]

^^^ You may well be right. I'm quite stupid re: molecular chemistry. I did think the iodine did increase instability and this powder has been through many environmental changes (heat & cool, humidity & dryness) compared to any of the other 2Cs I have personal knowledge of.

The subjective effects were quite different than what I was used to, but they may have been set & setting, no hopes except for some bliss and in a natural and firendly outdoorsy environment compared to my other 2ci experiences which have all been very urban.

 

[C6H6]

2C-I is stable under the described conditions, any perceived change in activity is placebo. If there was a chemical decay, it would simply lead to a less potent product, but not one qualitatively different.