4-Fluoro-5-methoxy-DMT

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]

4-Fluoro-5-methoxy-DMT
Identifiers
IUPAC name
  • 4-Fluoro-5-Methoxy-N,N-dimethyltryptamine
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC13H17FN2O
Molar mass236.290 g·mol−1
3D model (JSmol)
SMILES
  • CN(C)CCC1=CNC2=C1C(=C(C=C2)OC)F
InChI
  • InChI=1S/C13H17FN2O/c1-16(2)7-6-9-8-15-10-4-5-11(17-3)13(14)12(9)10/h4-5,8,15H,6-7H2,1-3H3
  • Key:CTEKFOKTEGQYLO-UHFFFAOYSA-N
  (verify)

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

References
  1. Blair JB, Kurrasch-Orbaugh D, Marona-Lewicka D, Cumbay MG, Watts VJ, Barker EL, Nichols DE (November 2000). "Effect of ring fluorination on the pharmacology of hallucinogenic tryptamines". Journal of Medicinal Chemistry. 43 (24): 4701–10. doi:10.1021/jm000339w. PMID 11101361.
  2. Laban U, Kurrasch-Orbaugh D, Marona-Lewicka D, Nichols DE (March 2001). "A novel fluorinated tryptamine with highly potent serotonin 5-HT1A receptor agonist properties". Bioorganic & Medicinal Chemistry Letters. 11 (6): 793–5. doi:10.1016/S0960-894X(01)00062-2. PMID 11277522.
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