5-MeO-DALT: the freebase of <i>N</i>,<i>N</i>-diallyl-5-methoxytryptamine

Chadeayne, Andrew R.; Pham, Duyen N. K.; Golen, James A.; Manke, David R.

doi:10.1107/s2414314620004988

Cited by 7 publications

(5 citation statements)

References 24 publications

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“…mushrooms [82]. In addition, several synthetic tryptamines, including 5-MeO-DALT (5-methoxy-N,N-diallyltryptamine) [83] and 4-AcO-DMT (4-acetoxy-N,Ndimethyltryptamine) [84], exhibit pronounced psychoactive effects and have emerged on illicit drug markets as substitutes for classic psychedelics [85].…”

Section: Tryptaminesmentioning

confidence: 99%

New Psychoactive Substances: Health and Legal Challenges

Santos,

Maia,

Dinis-Oliveira

et al. 2024

Psychoactives

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Drug abuse represents a significant public health problem with a growing tendency. As a way of circumventing the strict national and international control of psychoactive substances by regulatory agencies, there is a market release of new substances with psychoactive activity, called New Psychoactive Substances (NPSs). This group of substances encompasses a diverse range of synthetic compounds designed to mimic the effects of traditional illicit substances. As NPSs show stronger psychoactive effects than classical drugs, they pose unique challenges to public health and regulatory frameworks. Additionally, some substances are considered NPSs in some countries but not in others. Therefore, based on a given legal definition, manufacturers can create an NPS that does not fall under that definition and thus is not prohibited. This review critically explores the multifaceted dimensions of the criminal and legal contexts associated with NPSs. It examines the trends of abuse, the intricate network of criminal and legal aspects surrounding these substances, and the crucial warning signs that indicate their emergence, highlighting the health risks posed by these substances. In conclusion, this manuscript addresses the intricate interplay between the pharmacology, risks, and regulatory responses. These multifaceted challenges associated with NPSs will likely provide valuable insights for future research.

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Section: Tryptaminesmentioning

confidence: 99%

New Psychoactive Substances: Health and Legal Challenges

Santos,

Maia,

Dinis-Oliveira

et al. 2024

Psychoactives

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“…N-methyltryptamine (QQQAHA: Bergin et al, 1968). There are nine other 4-hydroxytryptamines reported in the literature, the natural product psilocin (PSILIN: Petcher & Weber, 1974), 4-hydroxy-N-methyl-N-isopropyltryptamine as its fumarate (TUFQAP: Chadeayne et al, 2020a) and hydrofumarate (RONSUL: Chadeayne et al, 2019a) salts, 4-hydroxy-N,N-di-n-propyltryptamine as its chloride (WAMGEA: Sammeta et al, 2020) and fumarate (WUCGAF: Chadeayne et al, 2019b) salts, and the four quaternary tryptamines 4-hydroxy-N,N,N-trimethyltryptamine (XUXFAA: Chadeayne et al, 2020c), 4-hydroxy-N,N-dimethyl-N-ethyltryptamine, 4-hydroxy-N,N-dimethylisopropyltryptamine, and 4-hydroxy-N,Ndi-n-propyltryptamine (EDOYIJ, EDOYUV and EDOZIK: Glatfelter et al, 2022a). The reported structures most closely related to compound (2) are indole-3-yl-N-isopropylglyoxalylamide (HUNCID: Mansell et al, 2009), 4-benzyloxyindole-3-yl-N,N-diisopropylglyoxalylamide (RUHYEY: Spaeth et al, 1997) and 4-acetoxyindole-3-yl-N,N-diethylglyoxalylamide (AVUMOT: Wu et al, 2004).…”

Section: Database Surveymentioning

confidence: 99%

Synthesis and structure of 4-hydroxy-N-isopropyltryptamine (4-HO-NiPT) and its precursors

Laban¹,

Naeem²,

Chadeayne³

et al. 2023

Acta Cryst E

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The title compound, 4-hydroxy-N-isopropyltryptamine (4) or 4-HO-NiPT (systematic name: 3-{2-[(propan-2-yl)amino]ethyl}-1H-indol-4-ol), C13H18N2O, was synthesized in three steps from 4-benzyloxyindole (1) (systematic name: 4-phenoxy-1H-indole), C15H13NO. (1) was treated with oxalyl chloride and isopropylamine to produce N-isopropyl-4-benzyloxy-3-indoleglyoxylamide (2) {systematic name: 2-[4-(benzyloxy)-1H-indol-3-yl]-2-oxo-N-(propan-2-yl)acetamide}, C20H20N2O3. (2) was reduced to generate 4-benzyloxy-N-isopropyltryptamine (3) or 4-HO-NiPT, which was characterized as its chloride salt 4-benzyloxy-N-isopropyltryptammonium chloride (3a) (systematic name: {2-[4-(benzyloxy)-1H-indol-3-yl]ethyl}(propan-2-yl)azanium chloride), C20H25N2O·Cl. Finally the benzyl group of (3) was removed via hydrogenation to generate 4-HO-NiPT. The crystal structures of the title compound and all three synthetic precursors are presented.

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“…There are six other monoalkyltryptamine structures reported in the literature. These are the natural product norpsilocin, 4-hydroxy-N-methyltryptamine, which has been reported as its free base and its fumarate salt (MULXAV and MULXEZ; Chadeayne et al, 2020), the natural product baeocystin (FEJBAB; Naeem et al, 2022b), 4-acetoxy-N-methyltryptamine (Glatfelter et al, Symmetry codes: (i) x À 1 2 ; Ày; z À 1 2 ; (ii The structure of serotonin has also been determined as its hydrogen oxalate salt (SERHOX: Amit et al, 1978).…”

Section: Structure Descriptionmentioning

confidence: 99%

N-Methylserotonin hydrogen oxalate

Naeem,

Anas,

Chadeayne

et al. 2023

IUCr Data

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The solid-state structure of N-methylserotonin {systematic name: [2-(5-hydroxy-1H-indol-3-yl)ethyl](methyl)azanium hydrogen oxalate}, C11H15N2O+·C2HO4 −, is reported. The structure possesses a singly protonated N-methylserotonin cation and one hydrogen oxalate anion in the asymmetric unit. In the crystal, the molecules are linked by N—H...O and O—H...O hydrogen bonds into a three-dimensional network.

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5-MeO-DALT: the freebase of N,N-diallyl-5-methoxytryptamine

Cited by 7 publications

References 24 publications

New Psychoactive Substances: Health and Legal Challenges

New Psychoactive Substances: Health and Legal Challenges

Synthesis and structure of 4-hydroxy-N-isopropyltryptamine (4-HO-NiPT) and its precursors

N-Methylserotonin hydrogen oxalate

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