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

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

IUPAC name (RS)-2-[4-(2-Fluoro-ethyl)-2,5-dimethoxy-phenyl]-1-methyl-ethylamine
Other names 1-[4-(2-fluoroethyl)-2,5-dimethoxyphenyl]propan-2-amine
Identifiers
CAS number	^N
ChemSpider	^Y
ChEMBL	^Y
Jmol-3D images	Image 1 Image 2
SMILES C1(=CC(=C(C=C1CC(C)N)OC)CCF)OC COc1cc(CC(C)N)c(cc1CCF)OC
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
Properties
Molecular formula	C₁₃H₂₀NO₂F
Molar mass	241.31 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N Y/N?)

DOEF, or 4-fluoro ethyl-2,5-methoxy amphetamine, is a lesser-known psychedelic drug and a substituted amphetamine. DOEF was first synthesized by Alexander Shulgin. In his book PiHKAL (Phenethylamines i Have Known And Loved), the dosage range is listed as 2-3.5[mg], and the duration is listed as 12–16 hours. DOEF produces increased appreciation of music, closed-eye visuals, increased sexual pleasure, and intense slowing of time. Very little data exists about the pharmacological properties, metabolism, and toxicity of DOEF.

References

External links

PiHKALDOEF Entry in
DOEF Entry in PiHKAL • info

Hallucinogens

Psychedelics
5-HT_2AR agonists

Lysergamides	AL-LAD ALD-52 BU-LAD IP-LAD Diallyllysergamide Dimethyllysergamide Ergometrine ETH-LAD LAE-32 LPD-824 LSA LSD LSD-Pip LSH LSM-775 Lysergic acid 2-butyl amide LSZ Lysergic acid 3-pentyl amide Methylergometrine Methylisopropyllysergamide Methysergide N1-Methyl-lysergic acid diethylamide PARGY-LAD PRO-LAD

Phenethylamines	Aleph 2-(2,5-Dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine 2-Methyl-MDA 2C-B 2C-B-Dragonfly 2C-B-FLY 2CB-Ind βk-2C-B 2C-C 2C-C-FLY 25C-NBOMe 25CN-NBOH 25CN-NBOMe 25D-NBOMe 2C-D 2C-D-FLY 2C-E 2C-E-FLY 25E-NBOMe 2C-EF 2C-F 25F-NBOMe 2C-G 25G-NBOMe 25H-NBOMe 2C-I 2C-IP 2C-I-FLY 2C-N 25N-NBOMe 2C-O 2C-O-4 2C-P 2C-T 2C-T-2 2C-T-4 25T4-NBOMe 2C-T-7 2C-T-7-FLY 25T7-NBOH 2C-T-8 2C-T-13 2C-T-15 2C-T-17 2C-T-19 2C-T-21 2C-TFM 25TFM-NBOMe 2C-YN 2C-V 2CBCB-NBOMe 2CBFly-NBOMe 2CD-5EtO 25B-NBOMe 25B-NBOH 25C-NBOH 25I-NBMD 25I-NBOH 25I-NBF 25I-NBOMe 25P-NBOMe 3C-AL 3C-E 3C-P 5-APB 5-APDB 5-APDI 5-Methyl-MDA 6-APB 6-APDB 6-Methyl-MDA Br-DFLY DESOXY DMMDA DMMDA-2 DOB DOB-FLY DOC DOEF DOET DOF DOI DOM DOM-FLY DON DOPR DOTFM BOB BOD Escaline Ganesha HOT-2 HOT-7 HOT-17 Isoproscaline Jimscaline Lophophine Macromerine MDA MDEA MDMA Mescaline Methallylescaline MMA MMDA MMDA-2 MMDA-3a MMDMA NBOMe-mescaline Proscaline TCB-2 TFMFly TMA

Piperazines	pFPP TMFPP mCPP

Tryptamines	1-Methyl-5-methoxy-diisopropyltryptamine 2,N,N-TMT 4,5-DHP-AMT 4,5-DHP-DMT 4-Acetoxy-DALT 4-Acetoxy-DET 4-Acetoxy-DiPT 4-Acetoxy-DMT 4-Acetoxy-DPT 4-Acetoxy-MiPT 4-HO-5-MeO-DMT 4-HO-DBT 4-HO-DPT 4-HO-MET 4-HO-MPMI 4-HO-MPT 4,N,N-TMT 4-Propionyloxy-DMT 5,6-diBr-DMT 5-AcO-DMT 5-Bromo-DMT 5-Me-MIPT 5-MeO-2,N,N-TMT 5-MeO-4,N,N-TMT 5-MeO-α,N,N-TMT 5-MeO-α-ET 5-MeO-α-MT 5-MeO-DALT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT 5-MeO-DPT 5-MeO-EiPT 5-MeO-MET 5-MeO-MiPT 5-MeO-MPMI 5-N,N-TMT 7,N,N-TMT α-ET α-MT α,N,N-TMT Aeruginascin Baeocystin Bufotenin DALT DBT DCPT DET DIPT DMT DPT EiPT Ethocin Ethocybin Ibogaine Iprocin MET Miprocin MiPT Norbaeocystin Noribogaine PiPT Psilocin Psilocybin Voacangine

Others	AL-38022A ALPHA Dimemebfe Efavirenz Elemicin M-ALPHA Myristicin RH-34

Dissociatives
NMDAR antagonists

Adamantanes	Amantadine Memantine Rimantadine

Arylcyclohexylamines	3-MeO-PCP 4-MeO-PCP Dieticyclidine Diphenidine Esketamine Ethketamine Eticyclidine Gacyclidine Ketamine Methoxetamine Methoxyketamine Neramexane PCPr Phencyclidine Rolicyclidine Tenocyclidine Tiletamine

Morphinans	Dextrallorphan Dextromethorphan Dextrorphan Racemethorphan Racemorphan

Others	2-MDP 8A-PDHQ Aptiganel Dexoxadrol Dizocilpine Etoxadrol Ibogaine Midafotel NEFA Nitrous oxide Noribogaine Perzinfotel Remacemide Selfotel Xenon

Deliriants
mAChR antagonists

Miscellaneous

Cannabinoids
CB₁R agonists

Phytocannabinoids	Cannabinol THC (Dronabinol) THCV (Cannabidiol has different mechanism of action)

Synthetic	4-HTMPIPO 5F-PB-22 AB-001 AB-005 A-836,339 AB-CHMINACA AB-FUBINACA AB-PINACA ADB-FUBINACA ADB-PINACA ADBICA AM-630 AM-679 AM-694 AM-1220 AM-1221 AM-1235 AM-1241 AM-1248 AM-2201 AM-2232 AM-2233 APICA APINACA CB-13 CP 47,497 CP 55,244 CP 55,940 DMHP HU-210 HU-308 JWH-007 JWH-015 JWH-018 JWH-019 JWH-030 JWH-073 JWH-081 JWH-098 JWH-116 JWH-122 JWH-149 JWH-167 JWH-182 JWH-193 JWH-198 JWH-200 JWH-203 JWH-210 JWH-250 JWH-251 JWH-398 JWH-424 JTE 7-31 JTE-907 Levonantradol MAM-2201 MDA-19 MN-25 NESS-0327 NESS-040C5 Nabilone Nabitan Org 28611 Parahexyl QUCHIC QUPIC RCS-4 RCS-8 SDB-006 STS-135 THC-O-acetate THC-O-phosphate UR-144 WIN 55,212-2 XLR-11

D₂R agonists

Apomorphine
Aporphine
Bromocriptine
Cabergoline
Lisuride
Memantine
Nuciferine
Pergolide
Piribedil
Pramipexole
Ropinirole
Rotigotine
Also indirect D₂ agonists, such as dopamine reuptake inhibitors (cocaine, methylphenidate), releasing agents (amphetamine, methamphetamine), and precursors (levodopa).

GABA_AR agonists

Inhalants
Mixed MOA

κOR agonists

MAO inhibitors

σR agonists

Others

Drugs from PiHKAL

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