2C-EF

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]

2C-EF

Clinical data
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
ATC code	None
Pharmacokinetic data
Metabolism	Deamination (MAOTooltip monoamine oxidase), demethylation, hydroxylation, acetylation, glucuronidation[2]
Duration of action	12 hours[1]
Identifiers
IUPAC name 2-[4-(2-fluoroethyl)-2,5-dimethoxyphenyl]ethan-1-amine
CAS Number	1222814-77-8
PubChem CID	44350106
ChemSpider	23206505
ChEMBL	ChEMBL421439
CompTox Dashboard (EPA)	DTXSID201336575
Chemical and physical data
Formula	C12H18FNO2
Molar mass	227.279 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=CC(=C(C=C1CCN)OC)CCF
InChI 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

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

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][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-HT_2A 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

Analogues

Analogues of 2C-EF include 2C-E, 2C-T-21, 2C-TFM, 2C-TFE, DOEF, and 2C-EF-FLY, among others.^[4][6][7][8]

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}

See also

• 2C (psychedelics)