2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine

2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine (DOEF; also known as dimethoxyfluoroethylamphetamine) is a lesser-known psychedelic drug and member of the DOx class.[1][2] DOEF was first synthesized by Alexander Shulgin. In his book PiHKAL, the dosage range is listed as 2–3.5 mg, and the duration is listed as 12–16 hours.[3] Very little data exists about the pharmacological properties, metabolism, and toxicity of DOEF.

2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine

Names
IUPAC name 1-[4-(2-fluoroethyl)-2,5-dimethoxyphenyl]propan-2-amine
Identifiers
CAS Number	121649-01-2^N
3D model (JSmol)	Interactive image Interactive image
ChEMBL	ChEMBL123685^Y
ChemSpider	21106293^Y
PubChem CID	14201982
CompTox Dashboard (EPA)	DTXSID00557322
InChI InChI=1S/C13H20FNO2/c1-9(15)6-11-8-12(16-2)10(4-5-14)7-13(11)17-3/h7-9H,4-6,15H2,1-3H3^Y Key: QLENKWFQUHHBKZ-UHFFFAOYSA-N^Y InChI=1/C13H20FNO2/c1-9(15)6-11-8-12(16-2)10(4-5-14)7-13(11)17-3/h7-9H,4-6,15H2,1-3H3 Key: QLENKWFQUHHBKZ-UHFFFAOYAO
SMILES C1(=CC(=C(C=C1CC(C)N)OC)CCF)OC COc1cc(CC(C)N)c(cc1CCF)OC
Properties
Chemical formula	C13H20FNO2
Molar mass	241.306 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References

1. Gerdes, John M.; Mathis, Chester A.; Shulgin, Alexander T. (1988). "Synthesis of 1-[2′,5′-dimethoxy-4′-(β-fluoroethyl)phenyl]-2-aminopropane:studies related to 18F-labeled serotonin receptor ligands". Tetrahedron Letters. 29 (50): 6537–6539. doi:10.1016/S0040-4039(00)82391-6.
2. Trachsel, Daniel (2012). "Fluorine in psychedelic phenethylamines". Drug Testing and Analysis. 4 (7–8): 577–590. doi:10.1002/dta.413. PMID 22374819.
3. DOEF Entry in PiHKAL