ChemInform Abstract: Synthesis and Pharmacological Examination of Benzofuran, Indan, and Tetralin Analogues of 3,4‐(Methylenedioxy)amphetamine.

Monte, Aaron; Marona‐Lewicka, Danuta; Cozzi, Nicholas V.; Nichols, David E.

doi:10.1002/chin.199413160

Cited by 15 publications

(27 citation statements)

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“…They are phenethylamine derivatives and related to methylenedioxyphenethylamines such as 3,4-methylenedioxy-methamphetamine (MDMA, Ecstasy) and 3,4-methylenedioxy-amphetamine (MDA), both classified as Class A drugs in the U.K. Benzofuran analogues of MDA were first synthesised in the early 1990s (Monte et al, 1993) and became prevalent as recreational drugs, also known as 'legal highs', nearly two decades later. They were permanently banned as Class B substances in the U.K. in 2014 (The…”

Section: Introductionmentioning

confidence: 99%

Combined in vitro and in silico approaches to the assessment of stimulant properties of novel psychoactive substances – The case of the benzofuran 5-MAPB

Sahai

Davidson

Khelashvili

et al. 2017

Progress in Neuro-Psychopharmacology and Biological Psychiatry

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Section: Introductionmentioning

confidence: 99%

Combined in vitro and in silico approaches to the assessment of stimulant properties of novel psychoactive substances – The case of the benzofuran 5-MAPB

Sahai

Davidson

Khelashvili

et al. 2017

Progress in Neuro-Psychopharmacology and Biological Psychiatry

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“…However, the effect of 5-MAPB and 2-MAPB has not been determined in vitro. Monte et al (1993) had postulated that because of their structural similarity to phenethylamines, benzofurans are likely to act as catecholamine-releasing or re-uptake-inhibiting agents. However, the effect of benzofurans on the extracellular monoamine level has not been verified in animal studies.…”

Section: Introductionmentioning

confidence: 99%

Novel psychoactive benzofurans strongly increase extracellular serotonin level in mouse corpus striatum

et al. 2016

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-We examined the effects of three benzofurans [1-(Benzofuran-5-yl)-N-methylpropan-2 -amine (5-MAPB), 1-(Benzofuran-2-yl)-N-methylpropan-2-amine (2-MAPB), and 1-(Benzofuran-5-yl)-N-ethylpropan-2-amine (5-EAPB)] on the extracellular monoamine level in mouse corpus striatum by the microdialysis method and compared them with the effects of psychoactive 3,4-Methylenedioxymethamphetamine (MDMA). The effects of benzofurans on the extracellular monoamine level were qualitatively analogous to that of MDMA, with an increase in serotonin (5-HT) level exceeding dopamine (DA) level. The effects of 2-MAPB and 5-EAPB were almost the same as the effect of MDMA. However, 5-MAPB strongly increased extracellular monoamine level than MDMA. These differences in the potency appear to have a structure-activity relationship. The administration of 5-MAPB (1.6 × 10 -4 mol/kg B.W.) resulted in the death of two-thirds of the mice. The same dose of MDMA did not cause any deaths. The administration of 5-MAPB (1.6 × 10 -4 mol/kg B.W.) produced a 3.41°C ± 0.28°C rise in rectal temperature after 1 hr, whereas the administration of MDMA (1.6 × 10 -4 mol/kg B.W.) produced an approximate 1.85°C ± 0.26°C rise. These results suggest that benzofurans have 5-HT toxicity similar to MDMA, and 5-MAPB has a higher risk of lethal intoxication than MDMA. Furthermore, 5-APB, the metabolic product of 5-MAPB demethylation, may be involved in the acute 5-HT toxicity and may cause lethal intoxication in mice.

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“…[3] Many different groups of NPS, such as synthetic cannabinoids, synthetic cathinones, phenethylamines, piperazines, and plant-based substances, etc., have been encountered by law enforcement. [5][6][7][8] Ring-substituted phenethylamines have been on the drug market for more than 50 years, but increased interest in these substances originated from the publication of PIHKAL. Many phenethylamine derivatives could produce psychoactive effects through modulation of the monoamine neurotransmitter systems, resulting in their abuse as stimulants, psychedelics, or entactogens.…”

Section: Introductionmentioning

confidence: 99%

Identification of five substituted phenethylamine derivatives 5‐MAPDB, 5‐AEDB, MDMA methylene homolog, 6‐Br‐MDMA, and 5‐APB‐NBOMe

Liu

Wang²,

Qian³

et al. 2016

Drug Testing and Analysis

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This paper reports analytical properties of five substituted phenethylamine derivatives seized from a clandestine laboratory. These five derivatives include 5-(2-methylaminopropyl)-2,3-dihydrobenzofuran (5-MAPDB, 1), 5-(2-aminoethyl)-2,3-dihydrobenzofuran (5-AEDB, 2), N,2-dimethyl-3-(3,4-methylenedioxyphenyl)propan-1-amine (MDMA methylene homolog, 3), 6-bromo-3,4-methylenedioxymethamphetamine (6-Br-MDMA, 4), and 1-(benzofuran-5-yl)-N-(2-methoxybenzyl)propan-2-amine (5-APB-NBOMe, 5). These compounds were identified by liquid chromatography-quadrupole time-of-flight mass spectrometry (LC-QTOF-MS), gas chromatography-mass spectrometry (GC-MS), and nuclear magnetic resonance spectroscopy (NMR). No analytical properties about compounds 1-4 have appeared until now, making this the first report on these compounds. Copyright © 2016 John Wiley & Sons, Ltd.

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ChemInform Abstract: Synthesis and Pharmacological Examination of Benzofuran, Indan, and Tetralin Analogues of 3,4‐(Methylenedioxy)amphetamine.

Cited by 15 publications

References 1 publication

Combined in vitro and in silico approaches to the assessment of stimulant properties of novel psychoactive substances – The case of the benzofuran 5-MAPB

Combined in vitro and in silico approaches to the assessment of stimulant properties of novel psychoactive substances – The case of the benzofuran 5-MAPB

Novel psychoactive benzofurans strongly increase extracellular serotonin level in mouse corpus striatum

Identification of five substituted phenethylamine derivatives 5‐MAPDB, 5‐AEDB, MDMA methylene homolog, 6‐Br‐MDMA, and 5‐APB‐NBOMe

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