DFMDA

Difluoromethylenedioxyamphetamine (DFMDA, DiFMDA) is a substituted derivative of 3,4-methylenedioxyamphetamine (MDA), which was developed by Daniel Trachsel and coworkers, along with the corresponding fluorinated derivatives of MDMA, MDEA, BDB and MBDB, with the aim of finding a non-neurotoxic drug able to be used as a less harmful substitute for entactogenic drugs 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 alpha-methyldopamine, it was hoped that the difluoromethylenedioxy bioisostere would show increased metabolic stability and less toxicity.^[1][2][3]

DFMDA

Clinical data
ATC code	none
Legal status
Legal status	CA: Schedule I DE: NpSG (Industrial and scientific use only) UK: Class A
Identifiers
IUPAC name 1-(2,2-Difluoro-1,3-benzodioxol-5-yl)propan-2-amine
CAS Number	910393-51-0 Y
PubChem CID	57467735
ChemSpider	26495356
UNII	8Q2ANL037S
CompTox Dashboard (EPA)	DTXSID10726729
Chemical and physical data
Formula	C10H11F2NO2
Molar mass	215.200 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(Cc1ccc2c(c1)OC(O2)(F)F)N
InChI InChI=1S/C10H11F2NO2/c1-6(13)4-7-2-3-8-9(5-7)15-10(11,12)14-8/h2-3,5-6H,4,13H2,1H3 Key:BHDXKBALNFHXDV-UHFFFAOYSA-N
NY (what is this?)  (verify)

These compounds have not yet been tested in animals to verify whether they show similar pharmacological activity to the non-fluorinated parent compounds, although in vitro binding studies show DFMDA to have a SERT affinity in between that of MDA and MDMA.^[4] It is also now generally accepted that MDMA neurotoxicity results from a variety of different causes and is not solely due to accumulation of alpha-methyldopamine,^[5][6][7] making it unclear how much less neurotoxic DFMDA and related drugs would be in practice.

See also

• 3,4-Ethylidenedioxyamphetamine (EIDA)
• 3,4-Isopropylidenedioxyamphetamine (IDA)