Indolealkylamine metabolism: Synthesis of deuterated indolealkylamines as metabolic probes
Philip E. Morris, Cheng Chiao
Journal of Labelled Compounds and Radiopharmaceuticals June 1, 1993 DOI: 10.1002/jlcr.2580330603 (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Theoretical or philosophical paper Peer reviewed |
|---|---|
| Measures | 1H NMR, 2H NMR, 13C NMR |
| Citations | 7 |
| Key points | Describes a synthesis route for deuterium-labeled DMT and 5-MeO-DMT via reduction of amide intermediates with lithium aluminum deuteride, with structures confirmed by 1H, 2H and 13C NMR. The authors state the labeled compounds are intended as probes for investigating MAO-mediated metabolism of these compounds through the in vivo kinetic isotope effect. |
Abstract
Abstract The synthesis of the deuterium labeled, endogenously occurring, indolealkylamine hallucinogens N,N‐dimethyltryptamine and 5‐methoxy‐N,N‐dimethyltryptamine via reduction of amide intermediates with lithium aluminum deuteride is described. The compounds were characterized with 1H, 2H and 13C NMR. These compounds were synthesized for use as probes for investigating the metabolism of these compounds by MAO via the in vivo kinetic isotope effect.
Citations in the library
Cited by 5
- Administration of N,N-dimethyltryptamine (DMT) in psychedelic therapeutics and research and the study of endogenous DMT Psychopharmacology January 22, 2022
- Distribution of the hallucinogens N,N-dimethyltryptamine and 5-methoxy-N,N-dimethyltryptamine in rat brain following intraperitoneal injection: application of a new solid-phase extraction LC-APcI-MS-MS-isotope dilution method. Journal of Chromatography. B, Biomedical Sciences and Applications February 10, 2001
- Synthesis of 131I derivatives of indolealkylamines for brain mapping Journal of Labelled Compounds and Radiopharmaceuticals August 1, 1997
- Microwave‐accelerated preparation and analytical characterization of 5‐ethoxy‐N,N‐dialkyl‐[α,α,β,β‐H4]‐ and [α,α,β,β‐D4]‐tryptamines Drug Testing and Analysis December 29, 2010
- Discovery and In Vitro Characterization of SPL028: Deuterated N,N-Dimethyltryptamine. ACS Medicinal Chemistry Letters September 14, 2023
Cites 3
- Hallucinogenic N-methylated indolealkylamines in the cerebrospinal fluid of psychiatric and control populations. The British Journal of Psychiatry February 1, 1978
- Dimethyltryptamine levels in blood of schizophrenic patients and control subjects Psychopharmacology 1976
- A review of recent studies of the biosynthesis and excretion of hallucinogens formed by methylation of neurotransmitters or related substances. Schizophrenia Bulletin 1976