The pKa values of DMT, 5-MeO-DMT, 5-HO-DMT, and related compounds.
amino group pKa - Alkaloid8.68 - DMT (dimethyltryptamine)
?.?? - DMT N-Oxide (dimethyltryptamine N-Oxide)
?.?? - 5-MeO-DMT (methoxybufotenin)
?.?? - 5-MeO-DMT N-Oxide (methoxybufotenin N-Oxide)
9.67 - 5-HO-DMT (bufotenine)
?.?? - 5-HO-DMT N-Oxide (bufotenine N-Oxide)
8.47 - 4-HO-DMT (psilocin)
?.?? - O-phosphoryl-4-HO-DMT (psilocybin)
hydroxyl group pKa - Alkaloid?.?? - 5-HO-DMT (bufotenine)
?.?? - 5-HO-DMT N-Oxide (bufotenine N-Oxide)
?.?? - 4-HO-DMT (psilocin)
XlogP - Alkaloid2.0 - DMT (dimethyltryptamine)
1.7 - DMT N-Oxide (dimethyltryptamine N-Oxide)
1.9 - 5-MeO-DMT (methoxybufotenin)
?.? - 5-MeO-DMT N-Oxide (methoxybufotenin N-Oxide)
1.6 - 5-HO-DMT (bufotenine)
1.3 - 5-HO-DMT N-Oxide (bufotenine N-Oxide)
1.6 - 4-HO-DMT (psilocin)
0.2 - O-phosphoryl-4-HO-DMT (psilocybin)
I cannot find some of the pKa values. The hydroxyl groups of psilocin and bufotenine are apparently weakly acidic, but I can't find their pKa values. If anyone knows their pKa please post it! Also, what use is the hydroxyl group’s pKa of psilocin and bufotenine? Can a strong base react with them?
Human blood has a pH of about 7.4. In order for an alkaloid to cross the blood brain barrier easily, it’s pKa should be close to or lower than 7.4 or else too much of the drug will get ionized when it comes into contact with human blood. Ionized drugs do not normally enter the brain. Also the XlogP should be high (about 1.5 or higher), meaning it’s water soluble should be low. A drug with a low XlogP will affect the body more than the brain. So for hallucinogens you want a high XlogP, the higher the better. The pKa of LSD is 7.8 and it’s XlogP is 2.1. Because of it’s high XlogP and it’s low pKa, it can very easily enter the brain. This is one reason why it is so potent compared to DMT, it's pKa is much lower and it's XlogP is higher.
XlogP and pKa aren't the only things that affect a drug's potency, but they are factors.
For extraction purposes SWIM really wants to know the pKa 5-MeO-DMT. It has a lower XlogP than DMT, and it absorbs better sublingually and is about 5-10 times stronger than DMT, so this means that its pKa is probably much lower than that of DMT.
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