Concise Synthesis of N,N-Dimethyltryptamine and 5-Methoxy-N,N-dimethyltryptamine Starting with Bufotenine from Brazilian Anadenanthera ssp

@article{Moreira2015ConciseSO,
  title={Concise Synthesis of N,N-Dimethyltryptamine and 5-Methoxy-N,N-dimethyltryptamine Starting with Bufotenine from Brazilian Anadenanthera ssp},
  author={Leandro A. Moreira and Maria M{\'a}rcia Murta and Claudia Cristina Gatto and Christopher William Fagg and Maria L. dos Santos},
  journal={Natural Product Communications},
  year={2015},
  volume={10}
}
Bufotenine (1, 5-hydroxy-N,N-dimethyltryptamine) was isolated from seeds of Anadenanthera spp., a tree widespread in the Brazilian cerrado, using an efficient acid-base shakeout protocol. The conversion of bufotenine into N,N-dimethyltryptamine (4) and 5-methoxy-N,N-dimethyltryptamine (5) was accomplished through an innovative and short approach featuring the use of novel bufotenine-aminoborane complex (7). Furthermore, an easy methodology for conversion of bufotenine into 5-hydroxy-N,N,N… Expand
2 Citations

Tables from this paper

Serotonin and dopamine derivatives from the Papua New Guinea zoantharian Zoanthus cf. sansibaricus
Abstract In our continuous search for bioactive natural products from marine zoantharians, three serotonin derivatives 1-3 and one dopamine analogue 4 together with the known ecdysteroidsExpand
Comparing the Detection of Endogenous Psychedelics in Individuals With and Without Alleged Mediumistic Experiences
TLDR
There were no differences between individuals with and without alleged mediumistic experiences concerning endogenous psychedelics, and both BT and DMT are highly sensitive to metabolism by monoamine oxidase and to N‐oxidation, and do not survive in the periphery for long. Expand

References

SHOWING 1-10 OF 30 REFERENCES
Noncompetitive Inhibition of Indolethylamine-N-methyltransferase by N,N-Dimethyltryptamine and N,N-Dimethylaminopropyltryptamine
TLDR
The demonstration of noncompetitive mechanisms for INMT inhibition implies the presence of an inhibitory allosteric site, which may illuminate new biochemical pathway(s) underlying the biology of INMT. Expand
Citrus genus plants contain N-methylated tryptamine derivatives and their 5-hydroxylated forms.
TLDR
It is conceivable that both Leaves and seeds represent the arrival point of a biosynthetic pathway aimed to provide Citrus plants with chemical defense against aggressors, supported by the finding that leaves and seeds are the parts of the plant where the highest levels of those compounds were found. Expand
Psychedelic 5-methoxy-N,N-dimethyltryptamine: metabolism, pharmacokinetics, drug interactions, and pharmacological actions.
5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT) belongs to a group of naturally-occurring psychoactive indolealkylamine drugs. It acts as a nonselective serotonin (5-HT) agonist and causes manyExpand
Pharmacokinetic Interactions between Monoamine Oxidase A Inhibitor Harmaline and 5-Methoxy-N,N-Dimethyltryptamine, and the Impact of CYP2D6 Status
TLDR
A unified PK model including the inhibition of MAO-A- and CYP2D6-catalyzed 5-MeO-DMT metabolism by harmaline was developed and may be further employed to predict harmaline and 5-Methoxy-N,N-dimethyltryptamine PK interactions at various doses, define the impact of CYP 2D6 status, and drive harmaline–5-Me O-D MT pharmacodynamics. Expand
A critical review of reports of endogenous psychedelic N, N-dimethyltryptamines in humans: 1955-2010.
TLDR
A critical review of 69 published studies reporting the detection or detection and quantitation of these compounds in human body fluids addresses the methods applied and the criteria used in the determination of the presence of DMT, MDMT, and HDMT. Expand
Effects of monoamine oxidase inhibitor and cytochrome P450 2D6 status on 5-methoxy-N,N-dimethyltryptamine metabolism and pharmacokinetics.
TLDR
Findings indicate that MAOI largely affects 5-MeO-DMT metabolism and pharmacokinetics, as well as bufotenine formation that is mediated by CYP2D6. Expand
Identification of 5-hydroxy-tryptamine (bufotenine) in takini (Brosimumacutifolium Huber subsp. acutifolium C.C. Berg, Moraceae), a shamanic potion used in the Guiana Plateau.
TLDR
This paper is the first thorough analysis of takini, a hallucinogen used by the shamans of several peoples in Suriname, French Guiana, and the region east of the Para in Brazil, and reveals that the active ingredient is bufotenine, and that this compound is only contained in the subspecies Brosimum acutifolium Huber subsp. Expand
Gas chromatographic analysis of dimethyltryptamine and beta-carboline alkaloids in ayahuasca, an Amazonian psychoactive plant beverage.
TLDR
A simple gas chromatographic method for the simultaneous determination of dimethyltryptamine and the main beta-carbolines found in ayahuasca preparations was developed and validated and can be useful to estimate administered doses in animals and humans for further pharmacological and toxicological investigations ofAyahuasca. Expand
Indole metabolism in Piptadenia peregrina
TLDR
An unusual enzymatic reaction: the direct hydroxylation of tryptamine to 5-hydroxytryptamine (5-HT) has been shown to occur in tissues of Piptadenia peregrina and it is suggested that the intermediates in the synthesis of bufotenine from tryptophan in this plant are tryptamines, 5-HT and N -methyl-5- HT. Expand
Antifouling properties of simple indole and purine alkaloids from the Mediterranean gorgonian Paramuricea clavata.
TLDR
In contrast to commercial antifoulants, bufotenine and 1,3,7-trimethylisoguanine showed significant antiadhesion activity against one bacterial strain while being nontoxic. Expand
...
1
2
3
...