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

Simon D. Brandt; Sally Freeman; Ian A. Fleet; Peter McGagh; John F. Alder

doi:10.1039/b407239c

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

Simon D. Brandt, Sally Freeman, Ian A. Fleet, Peter McGagh, John F. Alder

Research output: Contribution to journal › Article › peer-review

Abstract

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).

Original language	English
Pages (from-to)	1047-1057
Number of pages	10
Journal	Analyst
Volume	129
Issue number	11
DOIs	https://doi.org/10.1039/b407239c
Publication status	Published - Nov 2004

Keywords

Drug screening; Drugs of abuse; Forensic analysis; Mass spectrometry; Pharmaceutical analysis (prepn. of (methoxy)-N,N-bis(methylethyl)tryptamine (foxy methoxy), study of Speeter and Anthony synthetic route using electrospray ionization mass spectrometry and ESI-TOF-MS, and its application to drug screening); Electron ionization mass spectrometry; Time-of-flight mass spectrometry (prepn. of N,N-bis(methylethyl)(phenylmethoxy)tryptamine and study of Speeter and Anthony synthetic route using electrospray ionization mass spectrometry and ESI-time-of-flight mass spectrometry); NMR spectroscopy (prepn. of N,N-bis(methylethyl)(phenylmethoxy)tryptamine and study of Speeter and Anthony synthetic route using electrospray ionization mass spectrometry, ESI-time-of-flight mass spectrometry, and NMR)

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@article{8bc41caa3cee4160b5315c5dc8430583,

title = "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",

abstract = "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).",

keywords = "Drug screening; Drugs of abuse; Forensic analysis; Mass spectrometry; Pharmaceutical analysis (prepn. of (methoxy)-N,N-bis(methylethyl)tryptamine (foxy methoxy), study of Speeter and Anthony synthetic route using electrospray ionization mass spectrometry and ESI-TOF-MS, and its application to drug screening); Electron ionization mass spectrometry; Time-of-flight mass spectrometry (prepn. of N,N-bis(methylethyl)(phenylmethoxy)tryptamine and study of Speeter and Anthony synthetic route using electrospray ionization mass spectrometry and ESI-time-of-flight mass spectrometry); NMR spectroscopy (prepn. of N,N-bis(methylethyl)(phenylmethoxy)tryptamine and study of Speeter and Anthony synthetic route using electrospray ionization mass spectrometry, ESI-time-of-flight mass spectrometry, and NMR)",

author = "Brandt, {Simon D.} and Sally Freeman and Fleet, {Ian A.} and Peter McGagh and Alder, {John F.}",

year = "2004",

month = nov,

doi = "10.1039/b407239c",

language = "English",

volume = "129",

pages = "1047--1057",

journal = "Analyst",

issn = "0003-2654",

publisher = "Royal Society of Chemistry",

number = "11",

}

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, Simon D.; Freeman, Sally; Fleet, Ian A. et al.
In: Analyst, Vol. 129, No. 11, 11.2004, p. 1047-1057.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - 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

AU - Brandt, Simon D.

AU - Freeman, Sally

AU - Fleet, Ian A.

AU - McGagh, Peter

AU - Alder, John F.

PY - 2004/11

Y1 - 2004/11

N2 - 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).

AB - 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).

KW - Drug screening; Drugs of abuse; Forensic analysis; Mass spectrometry; Pharmaceutical analysis (prepn. of (methoxy)-N,N-bis(methylethyl)tryptamine (foxy methoxy), study of Speeter and Anthony synthetic route using electrospray ionization mass spectrometry

U2 - 10.1039/b407239c

DO - 10.1039/b407239c

M3 - Article

SN - 0003-2654

VL - 129

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JO - Analyst

JF - Analyst

IS - 11

ER -