2C-EF
Pharmaceutical compound
From Wikipedia, the free encyclopedia
2C-EF, also known as 4-(2-fluoroethyl)-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families.[3][4][1] It is the 2C analogue of the DOx psychedelic DOEF.[3][4] The drug is taken orally.[3][1] 2C-EF was first described in the literature by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved.[4]
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| Other names | 4-(2-Fluoroethyl)-2,5-dimethoxyphenethylamine; 2,5-Dimethoxy-4-(2-fluoroethyl)phenethylamine |
| Routes of administration | Oral[1] |
| Drug class | Serotonergic psychedelic; Hallucinogen |
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| Metabolism | Deamination (MAO), demethylation, hydroxylation, acetylation, glucuronidation[2] |
| Duration of action | 12 hours[1] |
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| Formula | C12H18FNO2 |
| Molar mass | 227.279 g·mol−1 |
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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.[4] 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.[1][3] This information was cited via personal communication with M. Mueller in 2006.[3]
Interactions
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][5] This may result in overdose and serious toxicity.[2][5]
Pharmacology
Pharmacodynamics
2C-EF is a serotonergic psychedelic and hence presumably acts as a serotonin 5-HT2A receptor agonist.[1]
Pharmacokinetics
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
History
2C-EF was originally named by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[4] However, he only speculated about it and never actually synthesized or tested it himself.[4] Subsequently, 2C-EF was synthesized and tested by others such as Daniel Trachsel.[9][6]: 770
Society and culture
Legal status
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.