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4-MeO-DMT

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4-MeO-DMT

4-Methoxy-N,N-dimethyltryptamine (4-MeO-DMT), is a tryptamine derivative which has some central activity in animal tests similar to that of related psychedelic tryptamine drugs, although with significantly lower potency than either 5-MeO-DMT or 4-hydroxy-DMT (psilocin).[1][2][3][4] The longer chain homologue 4-MeO-DET was not found to be active in man at doses up to 30 mg by mouth or smoked, but its isomer 4-MeO-MiPT was found to be weakly active in human trials.[5]

See also

  • 4-Acetoxy-DMT; O-acetyl-DMT; 4-AcO-DMT: It is often said to have similar effects to Magic Mushrooms and it is disputed that, serving as a pro-drug, it may produce psilocin by atmospheric degradation or in vivo hydrolysis by esterases. Psilocin is the major active principle in psilocybin mushrooms. Psilocybin, considered the other main active principle in these mushrooms, is also suspected to serve as a pro-drug to psilocin. There is no proof at this moment that elucidates the extent of activity that 4-AcO-DMT and psilocybin themselves have. It is also unclear how much reaches the brain before being metabolized to psilocin. A distinct possibility is that an equilibrium exists between psilocin and its pro-drugs. 4-AcO-DMT has a slower buildup and decline of effects than psilocin, suggesting altered pharmacokinetic properties as a result of the ester hydrolysis reaction. A similar phenomenon may apply to psilocybin; thus, the variation in relative amounts of psilocybin compared to psilocin found in Magic Mushrooms may produce a variation or range of pharmacokinetic profiles.
  • Alexander Shulgin, who synthesized and bio-assayed countless tryptamine analogues for the very first time, has mentioned his suspicion that, while 4-hydroxy moieties of tryptamine alkaloids can have a protective group such as an ester, it should readily be cleaved to yield the indolol (psilocin) as an active zwitterion.[5]

4-Methoxylated tryptamines can be expected to be partially metabolized through O-demethylation by CYP2D6 enzymes similar to 5-MeO-DMT metabolism.[6] The reduced qualitative effects and potency of 4-MeO-DMT compared to psilocin esters indicates that this reaction happens less readily than deamination by MAO-A. Active levels of psilocin do not seem to be produced or at least not comparable to 4-AcO-DMT and psilocybin, since observed effects are very different. Limited psychedelic effects from 4-MeO-DMT could indicate heavily modulated pharmacokinetics of limited levels of psilocin metabolite or they can serve as an example of intrinsic activity of 4-Hydroxy-N,N-alkyltryptamine esters and ethers.

  • 4-MeO-MiPT: Alexander Shulgin has explicitly documented the synthesis, chemical properties, and effects of 4-MeO-MiPT as the only 4-methoxy tryptamine in his book TiHKAL. 4-MeO-MiPT and 4-MeO-DMT are present on the research chemical grey market. There do not seem to be any other 4-methoxylated homologues available. As a result of Shulgin's publication, more is known about 4-MeO-MiPT, but not very much about 4-MeO-DMT.

References

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