Well if you ever get to see things like the controlled substances from Sigma-Aldrich, a lot of clinical drugs are labelled 'toxic' because it doesn't take much to produce disruptive CNS effects (the amphetamines spring to mind). AMT comes with a toxic label, but it was also used as a clinical drug in the USSR for quite a few years. Basically a toxic label means simply that it doesn't take much to disrupt your normal functioning to a significant degree, it doesn't mean that it's something that you can't ingest under any circumstances (5-fluoro AMT is a much more potent competetive inhibitor of MAO than AMT, although still not in the same potency league as the harmala alkaloids).
That said, I wouldn't disagree with the toxic labelling/classification of 5-methoxy AMT as even the dose that elicits psychedelic activity can make you puke and fill your hoggers (the squirts!
) simultaneously - a true torture psychedelic IMO
I came up with too many "CAUTION TOXIC" warnings where I didn't find the same warnings for "indole-3- ethyl-2-amino", (indole phenethylamines) or their dialkylated derivatives (DMT, DET, etc).
I would class 5-methoxy-N,N-diisoprpyltryptamine (an N,N-dialkylated tryptamine) as toxic if AMT gets that classification because of observed responses. After all, 10mg of 5-MeO DiPT is enough to make a lot of people suffer quite horribly, yet at that dose, AMT is fairly mild. At doses where AMT exerts a full psychedelic spectrum of activity, 5-MeO DiPT would have most people checking into an A&E dept because of the toxic effects (then again, IMO just about all of the 5-methoxydialkyltryptamines are horrible compounds in terms of their effects on my GI tract)
I would expect that alpha methyl TRYP's would be active for the reasons that have been previously knocked around by several of you guys about protection from MAOI's. Along with mono N-methylation, even better.
N-methylation of AMT causes a dramatic drop in activity - it seems that if you want an active tryptamine (or even ergoline) the sidechain nitrogen needs to be either a primary or tertiary amine; as secondary amines are the most basic of the three groups, I'd assume that there's a big ugly positively charged group not far from the aspartate residue which attracts the sidechain nitrogen (it can't be steric hinderance or tertiary amine tryptamines wouldn't be able to interact with it). Strangely, N,N,alpha-trimethyltryptamine seems to be a non-starter in the activity stakes as well - maybe the alpha methyl in combination with N-alkyl groups are in some way hindered, but this bit is all guesswork (I'm open to other viable ideas to explain that)
