4-MeO-DMT
Encyclopedia
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 hallucinogenic tryptamine drugs, although with significantly lower potency than either 5-MeO-DMT
or 4-hydroxy-DMT (psilocin)
. The longer chain homologue 4-MeO-DET was not found to be active at any dose tested, but its isomer 4-MeO-MiPT
was found to be weakly active in human trials.
4-Methoxylated tryptamines can be expected to be partially metabolized through O-demethylation by CYP2D6
enzymes similar to 5-MeO-DMT metabolism. 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.
Tryptamine
Tryptamine is a monoamine alkaloid found in plants, fungi, and animals. It is based around the indole ring structure, and is chemically related to the amino acid tryptophan, from which its name is derived...
derivative which has some central activity in animal tests similar to that of related hallucinogenic tryptamine drugs, although with significantly lower potency than either 5-MeO-DMT
5-MeO-DMT
5-MeO-DMT is a powerful psychedelic tryptamine. It is found in a wide variety of plant and psychoactive toad species and, like its close relatives DMT and bufotenin , it has been used as an entheogen by South American shamans for thousands of years.-Chemistry:5-MeO-DMT was first synthesized in...
or 4-hydroxy-DMT (psilocin)
Psilocin
Psilocin , an aromatic compound, sometimes also spelled psilocine, psilocyn, or psilotsin, is a psychedelic mushroom alkaloid. It is found in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin...
. The longer chain homologue 4-MeO-DET was not found to be active at any dose tested, but its isomer 4-MeO-MiPT
4-MeO-MiPT
4-MeO-MiPT, or 4-methoxy-N-methyl-N-isopropyltryptamine, is a lesser-known psychedelic drug. It is the 4-methoxy analog of MiPT. 4-MeO-MiPT was first synthesized by Alexander Shulgin. In his book TiHKAL , the minimum dosage is listed as 20-30 mg, and the duration listed as 4–6 hours...
was found to be weakly active in human trials.
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 it's pro-drugs.
- Alexander ShulginAlexander ShulginAlexander "Sasha" Theodore Shulgin is an American pharmacologist, chemist, artist, and drug developer.Shulgin is credited with the popularization of MDMA, commonly known as ecstasy, in the late 1970s and early 1980s, especially for psychopharmaceutical use and the treatment of depression and...
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.
4-Methoxylated tryptamines can be expected to be partially metabolized through O-demethylation by CYP2D6
CYP2D6
Cytochrome P450 2D6 , a member of the cytochrome P450 mixed-function oxidase system, is one of the most important enzymes involved in the metabolism of xenobiotics in the body. Also, many substances are bioactivated by CYP2D6 to form their active compounds...
enzymes similar to 5-MeO-DMT metabolism. 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-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.
- 4-MeO-MiPT4-MeO-MiPT4-MeO-MiPT, or 4-methoxy-N-methyl-N-isopropyltryptamine, is a lesser-known psychedelic drug. It is the 4-methoxy analog of MiPT. 4-MeO-MiPT was first synthesized by Alexander Shulgin. In his book TiHKAL , the minimum dosage is listed as 20-30 mg, and the duration listed as 4–6 hours...
: 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 most is known about 4-MeO-MiPT but not very much about 4-MeO-DMT.