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Systematic (IUPAC) name
Clinical data
312314-18-4 YesY
Chemical data
Formula C13H17FN2O
236,13 g/mol
 YesY (what is this?)  (verify)

4-Fluoro-5-Methoxy-N,N-dimethyltryptamine (4-F-5-MeO-DMT) was first described by David E. Nichols team in 2000. It is a potent 5-HT1A agonist. Substitution with the 4-fluorine markedly increased 5-HT1A selectivity over 5-HT2A/2C receptors with potency greater than that of the 5-HT1A agonist 8-OH-DPAT.[1]

The analog compound with the N,N-dialkyl substituents constrained into a pyrrolidine ring, is a slightly stronger agonist for the 5-HT1A receptor and retains the selectivity over the 5-HT2A/2C receptors.[2]

See also[edit]


  1. ^ Joseph B. Blair, Deborah Kurrasch-Orbaugh, Danuta Marona-Lewicka, Medhane G. Cumbay, Val J. Watts, Eric L. Barker, and David E. Nichols (2000). "Effect of Ring Fluorination on the Pharmacology of Hallucinogenic Tryptamines". Journal of Medicinal Chemistry 43 (24): 4701–4710. doi:10.1021/jm000339w. PMID 11101361. 
  2. ^ Uros Laban, Deborah Kurrasch-Orbaugh, Danuta Marona-Lewicka and David E. Nichols (2001). "A Novel Fluorinated Tryptamine with Highly Potent Serotonin 5-HT1A Receptor Agonist Properties". Bioorganic & Medicinal Chemistry Letters 11 (6): 793–795. doi:10.1016/S0960-894X(01)00062-2. PMID 11277522.