61-50-7

Usage

Biological Activity

Endogenous σ 1 receptor ligand and psychoactive plant compound (K i = 14.8 μ M). Binding to σ 1 inhibits voltage-gated Na + channels and is responsible for the behavioral effects of DMT. Also a 5-HT 2A receptor agonist and inhibitor of 5-HT uptake at plasma membrane serotonin transporters (SERT) (K i = 4.0 μ M).

InChI:InChI=1/C12H16N2/c1-14(2)8-7-10-9-13-12-6-4-3-5-11(10)12/h3-6,9,13H,7-8H2,1-2H3

Upstream product

• 3389-21-7 3-(2-bromoethyl)-1H-indole 
• 124-40-3 dimethyl amine 
• 29095-44-1 2-(1H-indol-3-yl)-N,N-dimethyl-2-oxoacetamide 
• 19718-92-4 4-(N,N-dimethylamino)butyraldehyde dimethyl acetal 
• 59-88-1 phenylhydrazine hydrochloride 
• 17274-65-6 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole 
• 72853-80-6 5,6-Dibromo-N,N-dimethyltryptamine 
• 161202-91-1 1-hydroxy-N,N-dimethyltryptamine 
• 61-54-1 tryptamine 
• 74-88-4 methyl iodide 
• 2155-94-4 N,N-dimethyl-2-propen-1-amine 
• 201230-82-2 carbon monoxide 
• 100-63-0 phenylhydrazine 
• 108-01-0 2-(N,N-dimethylamino)ethanol 

Downstream Products

• 15741-71-6 N-phthalimidotryptamine 
• 639795-10-1 1-(2-bromophenylsulphonyl)-N,N-dimethyltryptamine 
• 481661-82-9 N,N-dimethyl-1-(2'-bromobenzoyl)tryptamine 
• 1012860-57-9 1-phenylthio-N,N-dimethyltryptamine 
• 144034-80-0 rizatriptan 
• 145202-66-0 rizatriptan benzoate 
• 4560-13-8 dimethyl-[2-(2-phenyl-indol-3-yl)-ethyl]-amine 
• 22120-32-7 2-(5-chloro-1H-indol-3-yl)-N, N-dimethylethanamine 
• 17274-65-6 5-bromo-3-[2-(N,N-dimethylamino)ethyl]-1H-indole 
• 4335-93-7 3-(dimethylaminoethyl)-1-methoxyindole 
• 1019-45-0 N,N-dimethyl-5-methoxytryptamine 
• 487-93-4 bufotenin 

Relevant academic research and scientific papers

ALKALOIDS FROM THE HALLUCINOGENIC PLANT VIROLA SEBIFERA

Key Word Index - Virola sebifera; Myristicaceae; hallucinogenic plant; alkaloids; N-methyl-N-acetyltryptamine; N-methyl-N-formyltryptamine; 2-methyl-1,2,3,4-tetrahydro-β-carboline; N,N-dimethyltryptamine; N,N-dimethyltryptamine-N-oxide; N-monomethyltryptamine. - Bark of Virola sebifera used in the preparation of hallucinogenic snuffs and drinks in Venezuela has yielded N-methyl-N-formyltryptamine and N-methyl-N-acetyltryptamine, which exist in two rotameric forms reflecting hindered rotation around the carbon-nitrogen bond of the amide function.They were detected by HPLC as well as NMR. 2-Methyl-1,2,3,4-tetrahydro-β-carboline, N,N-dimethyltryptamine, its oxide and N-monomethyltryptamine were also identified.

Successful bridging from a peptide to a non peptide antagonist at the human tachykinin NK-2 receptor

Non peptide products have been found to show nanomolar binding and functional affinities at the human tachykinin NK-2 receptor. The new antagonists do not possess stereogenic centers and their thermal behaviour in solution is featured by a peculiar set of conformational stereoisomers. A macroscopic viewpoint is preferentially adopted to rationalize the obtained results.

qNMR: An applicable method for the determination of dimethyltryptamine in ayahuasca, a psychoactive plant preparation

Ayahuasca is an Amazonian plant beverage obtained by infusing the pounded stems of Banisteriopsis caapi in combination with the leaves of Psychotria viridis. P. viridis contains the psychedelic indole N,N-dimethyltryptamine (DMT). This association has a wide range of use in religious rituals around the world. In the present work, an easy, fast and non-destructive method by Nuclear Magnetic Resonance of proton (1H NMR) for quantification of DMT in ayahuasca samples was developed and validated. 2,5-Dimethoxybenzaldehyde (DMBO) was used as internal standard (IS). For this purpose, the area ratios produced by protons of DMT (N(CH3)2) at 2.70 ppm, singlet, (6H) and for DMBO (Ar(OCH3)2) at 3.80 and 3.89 ppm, doublet, (6H) were used for quantification. The lower limit of quantification (LLOQ) was 12.5 μg/mL and a good intra-assay precision was also obtained (relative standard deviation 1H NMR method is not time consuming and can be readily applied to monitor this tryptamine in plant preparations. We believe that qNMR can be used for identification and quantification of many plant-based products and metabolites with important advantages, while comparing with other analytical techniques.

THERAPEUTIC COMPOSITIONS COMPRISING DEUTERATED OR PARTIALLY DEUTERATED N,N-DIMETHYLTRYPTAMINE COMPOUNDS

The present invention relates to compositions comprising N,N-dimethyltryptamine, deuterated N,N-dimethyltryptamine and/or partially deuterated N,N-dimethyltryptamine. In particular, the present invention relates to compositions comprising a combination of N,N-dimethyltryptamine and 2% or more by weight of one or more deuterated N,N- dimethyltryptamine compound selected from α,α-dideutero-N,N-dimethyltryptamine and α,α,β,β-tetradeutero-N,N-dimethyltryptamine. Additional and alternative compositions of the present invention comprise a combination of N,N-dimethyltryptamine and 2% or more by weight of one or more partially deuterated N,N-dimethyltryptamine compound selected from α,β,β-trideutero-N,N-dimethyltryptamine, α,β-dideutero-N,N- dimethyltryptamine, and α-deutero-N,N-dimethyltryptamine. Methods of synthesising compositions of the present invention, and methods of use of presently described compositions in treating psychiatric or psychocognitive disorders, such as major depressive disorder, are also provided.

Ruthenium Pincer Complex Catalyzed Selective Synthesis of C-3 Alkylated Indoles and Bisindolylmethanes Directly from Indoles and Alcohols

Herein, we presented Ru-SNS complex that serves as a useful catalyst for C-3 alkylation of 1H-indoles with various aliphatic primary and secondary alcohols including cyclic alcohols as well as benzylic alcohols. The selective synthesis of bisindolylmethane derivatives is also achieved from the same set of indole and alcohol just by altering the reaction parameters. Furthermore, the sustainable synthesis of C-3 alkylated indoles directly from 2-(2-nitrophenyl)ethan-1-ol and alcohols catalysed by a Ru-complex via “borrowing hydrogen” strategy is reported. This protocol provides an atom-economical sustainable route to access structurally important compounds like arundine, vibrindole A and tryptamine based derivatives. (Figure presented.).

Indole derivatives and its application on the medicament

The invention provides indole derivatives or stereisomers, tautomers, nitrogen oxides, solvate, metabolic products, pharmaceutically acceptable salts or prodrugs thereof for treating the alzheimer disease. The invention further discloses a pharmaceutical composition containing the compounds and a method of using the compounds or the pharmaceutical composition thereof to treat the alzheimer disease.

Reduction and Reductive Deuteration of Tertiary Amides Mediated by Sodium Dispersions with Distinct Proton Donor-Dependent Chemoselectivity

A practical and scalable single electron transfer reduction mediated by sodium dispersions has been developed for the reduction and reductive deuteration of tertiary amides. The chemoselectivity of this method highly depends on the nature of the proton donor. The challenging reduction via C-N bond cleavage has been achieved using Na/EtOH, affording alcohol products, while the use of Na/NaOH/H2O leads to the formation of amines via selective C-O scission. Sodium dispersions with high specific surface areas are crucial to obtain high yields and good chemoselectivity. This new method tolerates a range of tertiary amides. Moreover, the corresponding reductive deuterations mediated by Na/EtOD-d1 and Na/NaOH/D2O afford useful α,α-dideuterio alcohols and α,α-dideuterio amines with an excellent deuterium content.

Well-Defined Phosphine-Free Iron-Catalyzed N-Ethylation and N-Methylation of Amines with Ethanol and Methanol

An iron(0) complex bearing a cyclopentadienone ligand catalyzed N-methylation and N-ethylation of aryl and aliphatic amines with methanol or ethanol in mild and basic conditions through a hydrogen autotransfer borrowing process is reported. A broad range of aromatic and aliphatic amines underwent mono- or dimethylation in high yields. DFT calculations suggest molecular hydrogen acts not only as a reducing agent but also as an additive to displace thermodynamic equilibria.

Benzocarbazoles heterocyclic compound and its preparation and use (by machine translation)

The present invention provides a class of non-nucleoside anti-viral inhibitors, in particular to such as shown in formula I benzo heterocyclic compound or its pharmaceutically acceptable salt or hydrate, the invention also provides the compound or its pharmaceutically acceptable salt or hydrate of the preparation method. Pharmacological test indicates that the compound or its pharmaceutically acceptable salt or hydrate can effectively inhibit hepatitis b virus DNA replication and hepatitis c virus RNA replication, therefore, the invention also provides the compounds in the preparation of preventing and/or the treatment of viral infections, particularly hepatitis b virus (HBV) infection, hepatitis c virus (HCV) infection of use of the medicament. (by machine translation)

Marine AChE inhibitors isolated from Geodia barretti: Natural compounds and their synthetic analogs

Barettin, 8,9-dihydrobarettin, bromoconicamin and a novel brominated marine indole were isolated from the boreal sponge Geodia barretti collected off the Norwegian coast. The compounds were evaluated as inhibitors of electric eel acetylcholinesterase. Barettin and 8,9-dihydrobarettin displayed significant inhibition of the enzyme, with inhibition constants (Ki) of 29 and 19 μM respectively towards acetylcholinesterase via a reversible noncompetitive mechanism. These activities are comparable to those of several other natural acetylcholinesterase inhibitors of marine origin. Bromoconicamin was less potent against acetylcholinesterase, and the novel compound was inactive. Based on the inhibitory activity, a library of 22 simplified synthetic analogs was designed and prepared to probe the role of the brominated indole, common to all the isolated compounds. From the structure-activity investigation it was shown that the brominated indole motif is not sufficient to generate a high acetylcholinesterase inhibitory activity, even when combined with natural cationic ligands for the acetylcholinesterase active site. The four natural compounds were also analysed for their butyrylcholinesterase inhibitory activity in addition and shown to display comparable activities. The study illustrates how both barettin and 8,9-dihydrobarettin display additional bioactivities which may help to explain their biological role in the producing organism. The findings also provide new insights into the structure-activity relationship of both natural and synthetic acetylcholinesterase inhibitors.