Synthesis and Characterization of 5-MeO-DMT Succinate for Clinical Use

Sherwood, Alexander M.; Claveau, Romain; Lancelotta, Rafael; Kaylo, Kristi; Lenoch, Kelsey

doi:10.1021/acsomega.0c05099

Cited by 23 publications

(20 citation statements)

References 51 publications

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“…There were two papers in this review that aimed to create salt forms of psychedelic substances. Cozzi and Daley ( 86 ) made DMT hemifumurate salt and Sherwood et al ( 84 ) made 5-MeO-DMT succinate salt; these are both molecules that have been used significantly less in clinical trials compared to psilocybin. Previous research investigating consumption of DMT and 5-MeO-DMT in a naturalistic setting noted that the administration for these substances have primarily been through oral administration of ayahuasca for DMT ( 144 ) and the inhalation of vapour for 5-MeO-DMT ( 136 , 137 ).…”

Section: Discussionmentioning

confidence: 99%

“…Two research groups used 1 H NMR spectroscopy during the process of synthesising psychedelic molecules into their water-soluble salt forms. Sherwood et al ( 84 ), synthesised 5-MeO-DMT succinate salt and Cozzi and Daley ( 86 ) synthesised DMT hemifumarate salt. The reactions used to synthesis these molecules were different; 5-MeO-DMT succinate salt was produced using a Fischer indole reaction, whereas the DMT hemifumarate salt was produced with a Speeter and Anthony approach.…”

Section: Methodsmentioning

confidence: 99%

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1H Nuclear Magnetic Resonance: A Future Approach to the Metabolic Profiling of Psychedelics in Human Biofluids?

2021

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While psychedelics may have therapeutic potential for treating mental health disorders such as depression, further research is needed to better understand their biological effects and mechanisms of action when considering the development of future novel therapy approaches. Psychedelic research could potentially benefit from the integration of metabonomics by proton nuclear magnetic resonance (1H NMR) spectroscopy which is an analytical chemistry-based approach that can measure the breakdown of drugs into their metabolites and their metabolic consequences from various biofluids. We have performed a systematic review with the primary aim of exploring published literature where 1H NMR analysed psychedelic substances including psilocin, lysergic acid diethylamide (LSD), LSD derivatives, N,N-dimethyltryptamine (DMT), 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT) and bufotenin. The second aim was to assess the benefits and limitations of 1H NMR spectroscopy-based metabolomics as a tool in psychedelic research and the final aim was to explore potential future directions. We found that the most current use of 1H NMR in psychedelic research has been for the structural elucidation and analytical characterisation of psychedelic molecules and that no papers used 1H NMR in the metabolic profiling of biofluids, thus exposing a current research gap and the underuse of 1H NMR. The efficacy of 1H NMR spectroscopy was also compared to mass spectrometry, where both metabonomics techniques have previously shown to be appropriate for biofluid analysis in other applications. Additionally, potential future directions for psychedelic research were identified as real-time NMR, in vivo1H nuclear magnetic resonance spectroscopy (MRS) and 1H NMR studies of the gut microbiome. Further psychedelic studies need to be conducted that incorporate the use of 1H NMR spectroscopy in the analysis of metabolites both in the peripheral biofluids and in vivo to determine whether it will be an effective future approach for clinical and naturalistic research.

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Section: Discussionmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

1H Nuclear Magnetic Resonance: A Future Approach to the Metabolic Profiling of Psychedelics in Human Biofluids?

2021

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“…Alternative Names: O-methyl-bufotenin, five-methoxy, The Power and Toad Venom 5-MeO-DMT (5-MeO) is a powerful psychoactive tryptamine able to be synthesised through botanical sources but also is present and can be extracted from the parotid secretions of the toad incilius alvaris. 95 5-MeO is considered approximately 5 times stronger than the closely related DMT and is thought to operate via the same mode of action. 95,96 Onset after inhalation is often fast, intense and fully enveloping with wide variations between users.…”

Section: -Meo-dmt (5-methoxy-nn-dimethyltryptamine)mentioning

confidence: 99%

'Tick, Tick, BOOM! Recent updates in the use of electronic cigarette technology as an illicit drug delivery system' - A multimodal review of how licit harm reduction devices are being co-opted into potential lethal weapons.

Dooley¹

2022

Preprint

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The vaporization of illicit drugs can be traced back to ancient times, to snuff boxes with traces of psychedelic drugs in Aztec tombs and opium pipes being found in the remains of many great ancient Chinese societies. The advancement of e-cigarette technology has resulted in a new and novel way to vaporize drugs, and while nicotine vaping remains their primary use, meta-analysis of online forums and statistical analysis indicates this is trend which is increasing in popularity. This paper aims to provide an update on the state of e-cigarettes being used as an illicit drug delivery system, the potential public health consequences of this kind of appropriation and a toxicological assessment of the most popular drugs being vaporised. A systematic review of online dark web marketplaces and online drug forums have formed the basis of this review. It can be concluded that this is a growing area of public health concern and one which should be continued to be monitored closely, particularly with respect to Novel Psychoactive Substances due to their continued and abundant proliferation and lack of research with respect to their toxicological profiles.

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“…It can be administered via inhalation or injection, but does not function as a psychedelic when consumed orally (Weil & Davis, 1994). A recent report described the synthesis of a water-soluble succinate salt of 5-MeO-DMT (Sherwood et al, 2020). 5-Methoxy-N,N-diallyltryptamine (5-MeO-DALT) is a synthetic analogue of 5-MeO-DMT, which was synthesized in 2004 by Alexander Shulgin (Shulgin & Shulgin, 2016).…”

Section: Chemical Contextmentioning

confidence: 99%

`Foxtrot' fumarate: a water-soluble salt of N,N-diallyl-5-methoxytryptamine (5-MeO-DALT)

Pham

Sammeta

Chadeayne³

et al. 2021

Acta Cryst E

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The title compound, bis(N,N-diallyl-5-methoxytryptammonium) (5-MeO-DALT) fumarate (systematic name: bis{N-[2-(5-methoxy-1H-indol-3-yl)ethyl]- N-(prop-2-en-1-yl)prop-2-en-1-aminium} (E)-but-2-enedioate), 2C17H23N2O+·C4H2O4 2−, has a single tryptammonium cation and half of a fumarate dianion in the asymmetric unit. The tryptammonium and fumarate ions are held together in one-dimensional chains by a series of N—H...O hydrogen bonds. These chains are combinations of R 4 4(22) rings, and C 2 2(14) and C 4 4(28) parallel chains along [111].

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Synthesis and Characterization of 5-MeO-DMT Succinate for Clinical Use

Cited by 23 publications

References 51 publications

1H Nuclear Magnetic Resonance: A Future Approach to the Metabolic Profiling of Psychedelics in Human Biofluids?

1H Nuclear Magnetic Resonance: A Future Approach to the Metabolic Profiling of Psychedelics in Human Biofluids?

'Tick, Tick, BOOM! Recent updates in the use of electronic cigarette technology as an illicit drug delivery system' - A multimodal review of how licit harm reduction devices are being co-opted into potential lethal weapons.

`Foxtrot' fumarate: a water-soluble salt of N,N-diallyl-5-methoxytryptamine (5-MeO-DALT)

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