TOXIC FLUORINE COMPOUNDS: XIII. Ω-Fluoroalkyl ETHERS

Pattison, F. L. M.; Howell, W. C.; Woolford, R. G.

doi:10.1139/v57-021

Cited by 15 publications

(4 citation statements)

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“…could possibly be metabolized to fluoroacetate. [60,61] But in general fluorine that is covalently bound to a carbon cannot be abstracted metabolically and will also leave the body at the same carbon. The only exceptions are acyl fluorides or analogous compounds.…”

Section: The Phenethylamine Pharmacophorementioning

confidence: 99%

“…Also certain fluorine compounds are considered to be among the most poisonous derivatives such as soman and sarin, both highly effective chemical warfare agents. [60,61] But in general fluorine that is covalently bound to a carbon cannot be abstracted metabolically and will also leave the body at the same carbon. [59] It shows its extreme toxic effects towards mammals wherein it cannot be distinguished from acetate; fluoroacetate underlies the same metabolic pathways (enzymatic transformations as follows: together with coenzyme A, fluoroacetate forms fluoroacetyl-CoA, which in the tricarboxylic acids cycle (TCA cycle) substitutes for acetyl-CoA.…”

Section: Introductionmentioning

confidence: 99%

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Fluorine in psychedelic phenethylamines

Trachsel¹

2012

Drug Testing and Analysis

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The so-called psychedelic phenethylamines represent a class of drugs with a large range of psychoactive properties in humans, ranging from naturally occurring mescaline to amphetamine analogues and homologues. The interest in many of these compounds, occasionally referred to as designer-drugs, is widely dispersed across popular culture and political and scientific communities. In recent decades, fluorine has become a powerful and important tool in medicinal chemistry. In addition, fluorine-containing compounds and medicines can be found in numerous commercially successful pharmaceuticals that have gained a market share of some 5-15%. One might anticipate this trend to increase in the future. As far as fluorinated phenethylamines are concerned, much less is known about their chemistry and pharmacology. This paper provides an overview regarding the biological properties of over 60 fluorinated phenethylamines and discusses both historical and recent chemistry-related developments. It was shown that the introduction of fluorine into the phenethylamine nucleus can impact greatly on psychoactivity of these compounds, ranging from marked loss to enhancement and prolongation of effects. For example, in contrast to the psychoactive escaline (70), it was observed that its fluoroescaline (76) counterpart was almost devoid of psychoactive effects. Difluoroescaline (77), on the other hand, retained, and trifluoroescaline (78) showed increased human potency of escaline (70). Difluoromescaline (72) and trifluoromescaline (73) increasingly surpassed human potency and duration of mescaline (22) effects.

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Section: The Phenethylamine Pharmacophorementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Fluorine in psychedelic phenethylamines

Trachsel¹

2012

Drug Testing and Analysis

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“…However, potentially adverse toxicological effects were reported [6][7][8][9][10] for a number of fluoroethers. Although this does not preclude the possibility of low toxicity fluoroethers, it is noteworthy and should be evaluated early on in the development of a fluoroether.…”

Section: Potential Chemical Familiesmentioning

confidence: 99%

Blowing Agents: The Next Generation

Decaire¹,

Pham²,

Richard³

et al. 1994

Journal of Cellular Plastics

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“…Alkali metal fluorides have also been used to replace halogens in aliphatic ethers. [12][13][14][15][16][17] We have used both the Swarts reaction and alkali metal fluorides to prepare the 34 fluoromethyl haloethyl ethers listed in Table I. The conditions of these fluorinations with the appropriate chloromethyl starting materials are summarized in Table II.…”

mentioning

confidence: 99%