Chemistry:2C-EF

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2C-EF, also known as 4-(2-fluoroethyl)-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families.[1][2][3] It is the 2C analogue of the DOx psychedelic DOEF.[1][2] The drug is taken orally.[1][3] 2C-EF was first described in the literature by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved.[2]

Use and effects

While 2C-EF was briefly mentioned by Alexander Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved), its properties and effects were not described.[2] Subsequently, in his book The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds, Shulgin listed 2C-EF's dose range as 6 to 12 mg orally and its duration as 12 hours.[3][1] This information was cited via personal communication with M. Mueller in 2006.[1]

Interactions

2C-EF is metabolized by monoamine oxidase (MAO) enzymes, including monoamine oxidase A (MAO-A) and/or monoamine oxidase B (MAO-B).[4] Monoamine oxidase inhibitors (MAOIs) such as phenelzine, tranylcypromine, moclobemide, and selegiline may potentiate the effects of 2C-EF.[4][5] This may result in overdose and serious toxicity.[4][5]

Pharmacology

Pharmacodynamics

2C-EF is a serotonergic psychedelic and hence presumably acts as a serotonin 5-HT2A receptor agonist.[3]

Pharmacokinetics

The metabolism of 2C-EF has been studied in vitro.[4] It undergoes demethylation at position 2 or 5, hydroxylation, and deamination, as well as acetylation and glucuronidation.[4] Oxidative deamination, mediated mainly by monoamine oxidase (MAO) enzymes, is the main route of metabolism for 2C-EF.[4]

Chemistry

Analogues

Analogues of 2C-EF include 2C-E, 2C-T-21, 2C-TFM, 2C-TFE, DOEF, and 2C-EF-FLY, among others.[2][6][7][8]

History

2C-EF was originally named by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[2] However, he only speculated about it and never actually synthesized or tested it himself.[2] Subsequently, 2C-EF was synthesized and tested by others such as Daniel Trachsel.[9][6]: 770 

Society and culture

Canada

2C-EF is a controlled substance in Canada under phenethylamine blanket-ban language.[10]

United States

2C-EF is not an explicitly controlled substance in the United States.[11] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. 1. Berkeley: Transform Press. 2011. ISBN 978-0-9630096-3-0. "2C-EF [...] (7,8) [...] (7) Not in the published scientific literature. (8) Orally active in humans at 6-10 mg; duration 12 hours (Mueller, 2006)." 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628. http://www.erowid.org/library/books_online/pihkal/pihkal.shtml.  "DOEF". https://erowid.org/library/books_online/pihkal/pihkal065.shtml. "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." 
  3. ↑ 3.0 3.1 3.2 3.3 "Comparison of the behavioral responses induced by phenylalkylamine hallucinogens and their tetrahydrobenzodifuran ("FLY") and benzodifuran ("DragonFLY") analogs". Neuropharmacology 144: 368–376. January 2019. doi:10.1016/j.neuropharm.2018.10.037. 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.". 
  4. ↑ 4.0 4.1 4.2 4.3 4.4 4.5 "Metabolic profiling of 2C-EF in human liver microsomes: Identification of major metabolites and biotransformation pathways". Toxicologie Analytique et Clinique. 2025. doi:10.1016/j.toxac.2025.08.005. 
  5. ↑ 5.0 5.1 "Drug-drug interactions involving classic psychedelics: A systematic review". Journal of Psychopharmacology 38 (1): 3–18. January 2024. doi:10.1177/02698811231211219. PMID 37982394. 
  6. ↑ 6.0 6.1 Phenethylamine: Von der Struktur zur Funktion. Nachtschatten Verlag AG. 2013. ISBN 978-3-03788-700-4. 
  7. ↑ "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. October 2019. doi:10.1002/dta.2675. PMID 31299701. 
  8. ↑ "How preclinical studies have influenced novel psychoactive substance legislation in the UK and Europe". British Journal of Clinical Pharmacology 86 (3): 452–481. March 2020. doi:10.1111/bcp.14224. PMID 32045495. 
  9. ↑ "The frontier orbital phase angles: novel QSAR descriptors for benzene derivatives, applied to phenylalkylamine hallucinogens". Journal of Medicinal Chemistry 41 (20): 3845–3856. September 1998. doi:10.1021/jm980144c. PMID 9748359. 
  10. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  11. ↑ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026, https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf 



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