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2C-EF

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2C-EF
Clinical data
Other names4-(2-Fluoroethyl)-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-(2-fluoroethyl)phenethylamine
Routes of
administration		Oral[1]
Drug classSerotonergic psychedelic; Hallucinogen
ATC code
  • None
Pharmacokinetic data
MetabolismDeamination (MAOTooltip monoamine oxidase), demethylation, hydroxylation, acetylation, glucuronidation[2]
Duration of action12 hours[1]
Identifiers
  • 2-[4-(2-fluoroethyl)-2,5-dimethoxyphenyl]ethan-1-amine
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H18FNO2
Molar mass227.279 g·mol−1
3D model (JSmol)
  • COC1=CC(=C(C=C1CCN)OC)CCF
  • InChI=1S/C12H18FNO2/c1-15-11-8-10(4-6-14)12(16-2)7-9(11)3-5-13/h7-8H,3-6,14H2,1-2H3
  • Key:KXPMRPNOYIOXFY-UHFFFAOYSA-N

2C-EF, also known as 4-(2-fluoroethyl)-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families.[3][1] It is the 2C analogue of the DOx psychedelic DOEF.[3] The drug is taken orally.[1] 2C-EF was first described in the literature in 1991.[3]

Use and effects

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2C-EF is an active psychedelic drug and has a dose range of 6 to 12 mg orally and duration of 12 hours.[1]

Interactions

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See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

2C-EF is metabolized by monoamine oxidase (MAO) enzymes, including monoamine oxidase A (MAO-A) and/or monoamine oxidase B (MAO-B).[2] Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C-EF.[2][4] This may result in overdose and serious toxicity.[2][4]

Pharmacology

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Pharmacodynamics

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2C-EF is a serotonergic psychedelic.[1]

Pharmacokinetics

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The metabolism of 2C-EF has been studied in vitro.[2] It undergoes demethylation at position 2 or 5, hydroxylation, and deamination, as well as acetylation and glucuronidation.[2] Oxidative deamination, mediated mainly by monoamine oxidase (MAO) enzymes, is the main route of metabolism for 2C-EF.[2]

Chemistry

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Analogues

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A notable derivative of 2C-EF is 2C-EF-FLY.[5][6]

History

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2C-EF was originally named by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[3] However, he only speculated about it and never actually synthesized or tested it himself.[3] Subsequently, 2C-EF was synthesized and tested by others such as Daniel Trachsel.[7][8]: 770 

See also

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References

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  1. ^ a b c d e f Halberstadt AL, Chatha M, Stratford A, Grill M, Brandt SD (January 2019). "Comparison of the behavioral responses induced by phenylalkylamine hallucinogens and their tetrahydrobenzodifuran ("FLY") and benzodifuran ("DragonFLY") analogs". Neuropharmacology. 144: 368–376. doi:10.1016/j.neuropharm.2018.10.037. PMC 6863604. PMID 30385253. According to Shulgin and Shulgin (1991), 2C-E is active at doses of 10–25 mg. 4-(2-Fluoroethyl)-2,5-dimethoxyphenethylamine (2C-EF) also reportedly acts as a hallucinogen and is orally active in humans at doses of 6–12 mg with a duration of 12 hours (Shulgin et al. 2011), although information about the extent of recreational use of this substance appears to be lacking.
  2. ^ a b c d e f g Arbouche N, Gheddar L, Ameline A, Raul JS, Kintz P (2025). "Metabolic profiling of 2C-EF in human liver microsomes: Identification of major metabolites and biotransformation pathways". Toxicologie Analytique et Clinique. doi:10.1016/j.toxac.2025.08.005.
  3. ^ a b c d e Shulgin A, Shulgin A (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. "DOEF". And I'll bet you dollars to doughnuts, that if one were to make the two-carbon analog 2,5-dimethoxy-4-(2-fluoroethyl)phenethylamine, it would be every bit as much a treasure and ally as is 2C-B or 2C-I. In fact, I am sure enough about this prediction that I am willing to name the stuff 2C-EF. It will be easily made from 2C-B by the same reaction scheme that was used above for DOEF. And I will even guess that its activity level will be in the 20–30 milligram area.
  4. ^ a b Halman A, Kong G, Sarris J, Perkins D (January 2024). "Drug-drug interactions involving classic psychedelics: A systematic review". Journal of Psychopharmacology. 38 (1): 3–18. doi:10.1177/02698811231211219. PMC 10851641. PMID 37982394.
  5. ^ Wagmann L, Hempel N, Richter LH, Brandt SD, Stratford A, Meyer MR (October 2019). "Phenethylamine-derived new psychoactive substances 2C-E-FLY, 2C-EF-FLY, and 2C-T-7-FLY: Investigations on their metabolic fate including isoenzyme activities and their toxicological detectability in urine screenings". Drug Testing and Analysis. 11 (10): 1507–1521. doi:10.1002/dta.2675. PMID 31299701.
  6. ^ Santos-Toscano R, Guirguis A, Davidson C (March 2020). "How preclinical studies have influenced novel psychoactive substance legislation in the UK and Europe". British Journal of Clinical Pharmacology. 86 (3): 452–481. doi:10.1111/bcp.14224. PMC 7080617. PMID 32045495.
  7. ^ Clare BW (September 1998). "The frontier orbital phase angles: novel QSAR descriptors for benzene derivatives, applied to phenylalkylamine hallucinogens". Journal of Medicinal Chemistry. 41 (20): 3845–3856. doi:10.1021/jm980144c. PMID 9748359.
  8. ^ Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: Von der Struktur zur Funktion. Nachtschatten Verlag AG. ISBN 978-3-03788-700-4.
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