DFMDA
Chemical compound
From Wikipedia, the free encyclopedia
DFMDA, also known as F2-MDA or as 3,4-(difluoromethylenedioxy)amphetamine, is a chemical compound of the phenethylamine, amphetamine, and MDxx families related to the entactogen and psychedelic drug MDA.[2][3][1] It is the derivative of MDA in which the two hydrogen atoms on the carbon atom of the 3,4-methylenedioxy ring have been replaced with fluorine atoms.[2][3][1]
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| Other names | F2-MDA; DiFMDA; Difluoro-MDA; 3,4-(Difluoromethylenedioxy)amphetamine |
| Routes of administration | Oral[1][2] |
| Drug class | Monoamine releasing agent; Serotonin releasing agent |
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| Duration of action | Unknown[1][2] |
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| Formula | C10H11F2NO2 |
| Molar mass | 215.200 g·mol−1 |
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Daniel Trachsel tested DFMDA in humans and found that it was inactive at doses of up to 250 mg orally.[1][2] Higher doses were not tested.[1][2] For comparison, he listed MDA's dose as 80 to 160 mg orally.[1]
DFMDA was active at the serotonin transporter (SERT) similarly to MDA and MDMA and with intermediate affinity between the two.[1][2]
It was developed with the aim of finding a non-neurotoxic drug able to be used as a less harmful substitute for entactogens such as MDMA. Since a major route of the normal metabolism of these compounds is scission of the methylenedioxy ring, producing neurotoxic metabolites such as α-methyldopamine, it was hoped that the difluoromethylenedioxy bioisostere would show increased metabolic stability and less toxicity.[3][4][5] These compounds have not yet been tested in animals to verify whether they show similar pharmacological activity to the non-fluorinated parent compounds.[6] It is also now generally accepted that MDMA neurotoxicity results from a variety of different causes and is not solely due to accumulation of α-methyldopamine,[7][8][9] making it unclear how much less neurotoxic DFMDA and related drugs would be in practice.
The chemical synthesis of DFMDA has been described.[3] Some notable analogues of DFMDA include DFMDMA (F2-MDMA), EIDA, and IDA, among others.[1][2] Other fluorinated MDxx derivatives, for instance derivatives of MDEA, BDB, and MBDB, have also been described.[3][2]
DFMDA was first described in the scientific literature by Daniel Trachsel and colleagues in 2006.[3] He described its properties and effects in humans in 2012 and 2013.[1][2]