4-MeO-DMT

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4-MeO-DMT
Systematic (IUPAC) name
2-(4-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine
Clinical data
Legal status ?
Identifiers
CAS number 3965-97-7 N
ATC code ?
PubChem CID 12017578
ChemSpider 23126449 YesY
ChEMBL CHEMBL32029 YesY
Chemical data
Formula C13H18N2O 
Mol. mass 218.29 g/mol
 N (what is this?)  (verify)

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

  1. ↑ Glennon RA, Young R, Benington F, Morin RD (February 1982). "Hallucinogens as discriminative stimuli: a comparison of 4-OMe DMT and 5-OMe DMT with their methythio counterparts". Life Sciences 30 (5): 465–7. doi:10.1016/0024-3205(82)90463-5. PMID 6801410. 
  2. ↑ Kline TB, Benington F, Morin RD, Beaton JM (August 1982). "Structure-activity relationships in potentially hallucinogenic N,N-dialkyltryptamines substituted in the benzene moiety". Journal of Medicinal Chemistry 25 (8): 908–13. doi:10.1021/jm00350a005. PMID 7120280. 
  3. ↑ Kline TB, Benington F, Morin RD, Beaton JM, Glennon RA, Domelsmith LN, Houk KN, Rozeboom MD (November 1982). "Structure-activity relationships for hallucinogenic N,N-dialkyltryptamines: photoelectron spectra and serotonin receptor affinities of methylthio and methylenedioxy derivatives". Journal of Medicinal Chemistry 25 (11): 1381–3. doi:10.1021/jm00353a021. PMID 6815326. 
  4. ↑ Nichols DE, Glennon RA. Medicinal Chemistry and Structure-Activity Relationships of Hallucinogens, in Hallucinogens, Neurochemical, Behavioral, and Clinical Perspectives (Raven Press 1984), pp 95-142. ISBN 978-0-89004-990-7
  5. ↑ 5.0 5.1 4-MeO-MiPT Entry in TIHKAL
  6. ↑ Shen, HW; Jiang, XL; Winter, JC; Yu, AM (2010). "Psychedelic 5-methoxy-N,N-dimethyltryptamine: Metabolism, pharmacokinetics, drug interactions, and pharmacological actions". Current drug metabolism 11 (8): 659–66. PMC 3028383. PMID 20942780. 
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