:4-Fluoro-5-methoxy-DMT

{{Short description|Chemical compound}}

{{Drugbox

| verifiedrevid = 451563257

| IUPAC_name = 4-Fluoro-5-Methoxy-N,N-dimethyltryptamine

| image = 4-Fluoro-5-methoxy-N,N-dimethyltryptamine.svg

| width =

| tradename =

| pregnancy_category =

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| protein_bound =

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 312314-18-4

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 3E926T8YGD

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| PubChem = 10082834

| ChemSpiderID = 8258372

| C=13 | H=17 | F=1 | N=2 | O=1

| smiles = CN(C)CCC1=CNC2=C1C(=C(C=C2)OC)F

| StdInChI = 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

| StdInChIKey = CTEKFOKTEGQYLO-UHFFFAOYSA-N

}}

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-HT_1A agonist. Substitution with the 4-fluorine markedly increased 5-HT_1A selectivity over 5-HT_2A/2C receptors with potency greater than that of the 5-HT_1A agonist 8-OH-DPAT.{{cite journal | vauthors = Blair JB, Kurrasch-Orbaugh D, Marona-Lewicka D, Cumbay MG, Watts VJ, Barker EL, Nichols DE | title = Effect of ring fluorination on the pharmacology of hallucinogenic tryptamines | journal = Journal of Medicinal Chemistry | volume = 43 | issue = 24 | pages = 4701–10 | date = November 2000 | pmid = 11101361 | doi = 10.1021/jm000339w }}

The analog compound with the N,N-dialkyl substituents constrained into a pyrrolidine ring, is a slightly stronger agonist for the 5-HT_1A receptor and retains the selectivity over the 5-HT_2A/2C receptors.{{cite journal | vauthors = Laban U, Kurrasch-Orbaugh D, Marona-Lewicka D, Nichols DE | title = A novel fluorinated tryptamine with highly potent serotonin 5-HT1A receptor agonist properties | journal = Bioorganic & Medicinal Chemistry Letters | volume = 11 | issue = 6 | pages = 793–5 | date = March 2001 | pmid = 11277522 | doi = 10.1016/S0960-894X(01)00062-2 }}