Synthesis and characterization of 5<i>H</i>‐1,3‐dioxolo[4,5‐<i>f</i>]indoleethylamines

Grotjahn, Douglas B.

doi:10.1002/jhet.5570200438

Cited by 7 publications

(3 citation statements)

References 21 publications

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“…N-CBA was prepared by the same method used to prepare the radioactive N-CBA. N-Methylcyclopropylamine was prepared as described by Grotjahn (1983). N-[1-3H]CBA was prepared as described by Silverman & Hoffman (1981) (sp act.…”

Section: Methodsmentioning

confidence: 99%

Revised mechanism for inactivation of mitochondrial monoamine oxidase by N-cyclopropylbenzylamine

Vazquez¹,

Silverman²

1985

Biochemistry

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A mechanism previously proposed for inactivation of monoamine oxidase (MAO) by N-cyclopropylbenzylamine (N-CBA) [Silverman, R. B., & Hoffman, S. J. (1980) J. Am. Chem. Soc. 102, 884-886] is revised. Inactivation of MAO by N-[1-3H]CBA results in incorporation of about 3 equiv of tritium into the enzyme and release of [3H]acrolein. Treatment of inactivated enzyme with benzylamine, a reactivator for N-CBA-inactivated MAO, releases only 1 equiv of tritium as [3H]acrolein concomitant with reactivation of the enzyme. Even after MAO is inactivated by N-[1-3H]CBA, the reaction continues. At pH 7.2, a linear release of [3H]acrolein is observed for 70 h, which produces 55 equiv of [3H]acrolein while 2.3 equiv of tritium is incorporated into the enzyme. At pH 9, only 3.5 equiv of [3H]acrolein is detected in solution after 96 h, but 40 equiv of tritium is incorporated into the enzyme, presumably as a result of greater ionization of protein nucleophiles at the higher pH. N-[1-3H]Cyclopropyl-alpha-methylbenzylamine (N-C alpha MBA) produces the same adduct as N-CBA but gives only 1-1.35 equiv of tritium bound after inactivation of the enzyme. Denaturation of labeled enzyme results in reoxidation of the flavin without release of tritium, indicating attachment is not to the flavin but rather to an amino acid residue. Enzyme inactivated with N-[1-3H]C alpha MBA is reactivated by benzylamine with the release of 1 equiv of [3H]acrolein, which must have come from an adduct attached to an active site amino acid residue.(ABSTRACT TRUNCATED AT 250 WORDS)

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Section: Methodsmentioning

confidence: 99%

Revised mechanism for inactivation of mitochondrial monoamine oxidase by N-cyclopropylbenzylamine

Vazquez¹,

Silverman²

1985

Biochemistry

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“…45,46 A similar phenomenon has been observed during the synthesis of psilocin analogues and for N,N-(disubstituted)-5,6-methylenedioxyindole-3-yl-glyoxalylamides. [47][48][49] The presence of the b-keto functional group reduces the electron density on the amide group which increases the rotational barrier when compared with simple amides. 50 Two fundamental differences, however, can be observed between the NMR spectra of 1-12 6 and 7).…”

Section: Nmr Spectroscopymentioning

confidence: 99%

Analytical chemistry of synthetic routes to psychoactive tryptamines : Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR

Brandt¹,

Freeman

Fleet

et al. 2005

Analyst

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The degree of alkylation of the side chain nitrogen in tryptamines is one important factor that affects psychoactivity. The method of Speeter and Anthony is considered to be one of the most important synthetic preparative methods. The final step in this reaction is based on the reduction of a (substituted) indole-3-yl-glyoxalylamide to the desired tryptamine with metal hydride. Twelve symmetrically and 13 asymmetrically N,N-disubstituted glyoxalylamides and their corresponding tryptamine derivatives have been synthesised and characterised by gas chromatography EI-ion trap mass spectrometry, electrospray-triple quadrupole-tandem mass spectrometry and NMR spectroscopy. Mass spectral and NMR similarities and differences between the investigated compounds are discussed. A solvent dependency is observed that has to be taken into consideration for the unambiguous assignment of (1)H- and (13)C-NMR chemical shifts. The (1)H-NMR study demonstrated that one can evaluate the rotamer populations of the asymmetrical glyoxalylamides. In a forensic or clinical scenario where single or multiple reaction monitoring approaches are contemplated, the appropriate ion transitions of choice may then focus on the two main fragmentations, namely beta-cleavage ([M+H](+)-->CH(2)N(+)R(2)R(3)) and/or alpha-cleavage ([M+H](+)-->[3-vinylindole](+)), respectively. The synthesis, NMR and MS analytical data presented provide the forensic analyst and clinical biochemist with a detailed and self-consistent body of information and mechanisms for the spectral identification of the more likely psychoactive tryptamines that may be met.

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“…A similar phenomenon has been reported during the synthesis of psilocin analogues 41,42 and for N,N-(disubstituted)-5,6-methylenedioxyindole-3-yl-glyoxalylamides. 43 For several glyoxalylamides Spaeth and coworkers 44 found a coalescence temperature of 80-150 uC and calculated that the rotation barriers in these amides were 10-15 kJ mol 21 higher than in simple acid amides like N,N-indole-3-acetamide that do not possess a b-carbonyl group.…”

Section: Implications Of the Nmr Datamentioning

confidence: 99%

Analytical chemistry of synthetic routes to psychoactive tryptamines : Part I. Characterisation of the Speeter and Anthony synthetic route to 5-methoxy-N,N-diisopropyltryptamine using ESI-MS-MS and ESI-TOF-MS

Brandt

Freeman

Fleet

et al. 2004

Analyst

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5-Methoxy-N,N-diisopropyltryptamine (5-MeO-DIPT), a new psychoactive tryptamine derivative, has been synthesised by the Speeter and Anthony procedure. This synthetic route was characterised by ESI-MS-MS, ESI-TOF-MS and NMR. Side products have been identified as 3-(2-N,N-diisopropylamino-ethyl)-1H-indol-5-ol (5), 2-N,N-diisopropylamino-1-(5-methoxy-1H-indol-3-yl)-ethanol (6), 2-(5-methoxy-1H-indol-3-yl)-ethanol (7) and 2-N,N-diisopropylamino-1-(5-methoxy-1H-indol-3-yl)-ethanone (8).

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Synthesis and characterization of 5H‐1,3‐dioxolo[4,5‐f]indoleethylamines

Cited by 7 publications

References 21 publications

Revised mechanism for inactivation of mitochondrial monoamine oxidase by N-cyclopropylbenzylamine

Revised mechanism for inactivation of mitochondrial monoamine oxidase by N-cyclopropylbenzylamine

Analytical chemistry of synthetic routes to psychoactive tryptamines : Part II. Characterisation of the Speeter and Anthony synthetic route to N,N-dialkylated tryptamines using GC-EI-ITMS, ESI-TQ-MS-MS and NMR

Analytical chemistry of synthetic routes to psychoactive tryptamines : Part I. Characterisation of the Speeter and Anthony synthetic route to 5-methoxy-N,N-diisopropyltryptamine using ESI-MS-MS and ESI-TOF-MS

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