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(Top) 1 See also 2 References

4-Fluoro-5-methoxy-DMT

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4-Fluoro-5-methoxy-DMT

Identifiers

4-Fluoro-5-Methoxy-N,N-dimethyltryptamine

312314-18-4^Y

10082834

8258372

CompTox Dashboard (EPA)

DTXSID001029532

Chemical and physical data

C₁₃H₁₇FN₂O

236.290 g·mol⁻¹

3D model (JSmol)

Interactive image

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

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

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.^[1]

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.^[2]

See also[edit]

References[edit]

^ 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.

^ 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.

Psychedelics
(5-HT_2A
agonists)

2C-B-FLY

Bromo-DragonFLY

Lyserg‐
amides

1B-LSD

2-Butyllysergamide

3-Pentyllysergamide

Diallyllysergamide

Dimethyllysergamide

Methylergometrine

Phenethyl‐
amines

2C-B

25x-NB

25B-NB

25x-NB3OMe

25B-NB3OMe

25x-NB4OMe

25B-NB4OMe

25x-NBF

25B-NBF

25x-NBMD

25B-NBMD

25x-NBOH

25B-NBOH

25x-NBOMe

25B-NBOMe

Atypical structures

25B-N1POMe

NBOMe-mescaline

25x-NMx

25B-NMe7BF

N-(2C)-fentanyl

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2C-B-DragonFLY-NBOH

2C-B-FLY-NB2EtO5Cl

2C-B-PP

alpha-alkyltryptamines

4,5-DHP-α-MT

x-DALT

(Daltocin) 4-HO-DALT

(Daltacetin) 4-AcO-DALT

x-DET

(Ethacetin) 4-AcO-DET

(Ethocin) 4-HO-DET

(Ethocybin) 4-PO-DET

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(Ipracetin) 4-AcO-DiPT

(Iprocin) 4-HO-DiPT

x-DMT

4,5-DHP-DMT

4-Propionyloxy-DMT

5-MeO-2,N,N-TMT

5-MeO-4,N,N-TMT

5-MeO-α,N,N-TMT

(Bufotenin) 5-HO-DMT

(Psilocin) 4-HO-DMT

(Psilocybin) 4-PO-DMT

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(Depracetin) 4-AcO-DPT

(Deprocin) 4-HO-DPT

(The Light) DPT

Ibogaine-related

18-MAC

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(Metocin) 4-HO-MET

(Metocetin) 4-AcO-MET

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(Mipracetin) 4-AcO-MiPT

(Miprocin) 4-HO-MiPT

(Moxy) 5-MeO-MiPT

Others

4-HO-DBT

(Lucigenol) 4-HO-MPMI

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Others

AL-38022A

RH-34
Also empathogens in general (e. g.: 5-APB, 5-MAPB, 6-APB and other substituted benzofurans).

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antagonists)

Arylcyclo‐
hexylamines

Ketamine-related

2-Fluorodeschloroketamine

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Esketamine ((S)-ketamine)

Methoxyketamine

PCP-related

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Deliriants
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Cannabinoids
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THC (Dronabinol)

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CP 47,497

HU-210

JWH-007

Misc. designer cannabinoids

4-HTMPIPO

5F-CUMYL-PINACA

ADAMANTYL-THPINACA

THC-O-phosphate

Apomorphine

Salvinorin A
Also indirect D₂ agonists, such as dopamine reuptake inhibitors (cocaine, methylphenidate), releasing agents (amphetamine, methamphetamine), and precursors (levodopa).

GABA_A
enhancers

CI-966

Muscimol (Amanita muscaria)

Inhalants
(Mixed MOA)

Aliphatic hydrocarbons
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Aromatic hydrocarbons

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2-EMSB

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Glaucine

Serotonin receptor modulators

Agonists: 8-OH-DPAT

Antidepressants (e.g., etoperidone, hydroxynefazodone, nefazodone, trazodone, triazoledione, vilazodone, vortioxetine)

Atypical antipsychotics (e.g., aripiprazole, asenapine, brexpiprazole, cariprazine, clozapine, lurasidone, quetiapine, ziprasidone)

Azapirones (e.g., buspirone, eptapirone, gepirone, perospirone, tandospirone)

Ergolines (e.g., bromocriptine, cabergoline, dihydroergotamine, ergotamine, lisuride, LSD, methylergometrine (methylergonovine), methysergide, pergolide)

Serotonin (5-HT)

Tryptamines (e.g., 5-CT, 5-MeO-DMT, 5-MT, bufotenin, DMT, indorenate, N-Me-5-HT, psilocin, psilocybin)

Antagonists: Atypical antipsychotics (e.g., iloperidone, risperidone, sertindole)

Beta blockers (e.g., alprenolol, carteolol, cyanopindolol, iodocyanopindolol, isamoltane, oxprenolol, penbutolol, pindobind, pindolol, propranolol, tertatolol)

Ergolines (e.g., metergoline)

Metitepine (methiothepin)

MIN-117 (WF-516)

Unknown/unsorted: Acetryptine

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Agonists: Anpirtoline

Ergolines (e.g., bromocriptine, dihydroergotamine, ergotamine, methylergometrine (methylergonovine), methysergide, pergolide)

Serotonin (5-HT)

Triptans (e.g., avitriptan, donitriptan, eletriptan, sumatriptan, zolmitriptan)

Tryptamines (e.g., 5-BT, 5-CT, 5-MT, DMT)

Antagonists: AR-A000002

Beta blockers (e.g., alprenolol, carteolol, isamoltane, oxprenolol, penbutolol, propranolol, tertatolol)

Ergolines (e.g., metergoline)

Metitepine (methiothepin)

Unknown/unsorted: Ergolines (e.g., cabergoline, ergometrine (ergonovine), lisuride)

Agonists: CP-122,288

Ergolines (e.g., bromocriptine, cabergoline, dihydroergotamine, ergotamine, LSD, methysergide)

Serotonin (5-HT)

Triptans (e.g., almotriptan, avitriptan, donitriptan, eletriptan, frovatriptan, naratriptan, rizatriptan, sumatriptan, zolmitriptan)

Tryptamines (e.g., 5-BT, 5-CT, 5-Et-DMT, 5-MT, 5-(nonyloxy)tryptamine, DMT)

Antagonists: Alniditan

Ergolines (e.g., metergoline)

Metitepine (methiothepin)

Unknown/unsorted: Acetryptine

Ergolines (e.g., lisuride, lysergol, pergolide)

Agonists: BRL-54443

Ergolines (e.g., methysergide)

Serotonin (5-HT)

Triptans (e.g., eletriptan)

Tryptamines (e.g., tryptamine)

Antagonists: Metitepine (methiothepin)

Unknown/unsorted: Ergolines (e.g., ergometrine (ergonovine), lysergol, methylergometrine (methylergonovine)

Agonists: BRL-54443

Ergolines (e.g., bromocriptine, lysergol, methylergometrine (methylergonovine) methysergide)

Serotonin (5-HT)

Triptans (e.g., eletriptan, naratriptan, sumatriptan)

Tryptamines (e.g., 5-MT)

Antagonists: Metitepine (methiothepin)

Agonists: 25H/NB series (e.g., 25I-NBF, 25I-NBMD, 25I-NBOH, 25I-NBOMe, 25B-NBOMe, 25C-NBOMe, 25TFM-NBOMe, 2CBCB-NBOMe, 25CN-NBOH, 2CBFly-NBOMe)

2Cs (e.g., 2C-B, 2C-E, 2C-I, 2C-T-2, 2C-T-7, 2C-T-21)

5-Methoxytryptamines (5-MeO-DET, 5-MeO-DiPT, 5-MeO-DMT, 5-MeO-DPT, 5-MT)

α-Alkyltryptamines (e.g., 5-Cl-αMT, 5-Fl-αMT, 5-MeO-αET, 5-MeO-αMT, α-Me-5-HT, αET, αMT)

Bromo-DragonFLY

DOx (e.g., DOB, DOC, DOI, DOM)

Ergolines (e.g., 1P-LSD, ALD-52, bromocriptine, cabergoline, ergine (LSA), ergometrine (ergonovine), ergotamine, lisuride, LA-SS-Az, LSB, LSD, LSD-Pip, LSH, LSP, methylergometrine (methylergonovine), pergolide)

MDxx (e.g., MDA (tenamfetamine), MDMA (midomafetamine), MDOH, MMDA)

Phenethylamines (e.g., lophophine, mescaline)

Piperazines (e.g., BZP, quipazine, TFMPP)

Serotonin (5-HT)

Tryptamines (e.g., 5-BT, 5-CT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine)

Antagonists: 5-I-R91150

Antihistamines (e.g., cyproheptadine, hydroxyzine, ketotifen, perlapine)

Atypical antipsychotics (e.g., amperozide, aripiprazole, asenapine, blonanserin, brexpiprazole, carpipramine, clocapramine, clorotepine, clozapine, fluperlapine, gevotroline, iloperidone, lurasidone, melperone, mosapramine, ocaperidone, olanzapine, paliperidone, quetiapine, risperidone, sertindole, zicronapine, ziprasidone, zotepine)

Chlorprothixene

Ergolines (e.g., amesergide, LY-53857, LY-215,840, mesulergine, metergoline, methysergide, sergolexole)

Metitepine (methiothepin)

MIN-117 (WF-516)

Opiranserin (VVZ-149)

Phenoxybenzamine

Serotonin antagonists and reuptake inhibitors (e.g., etoperidone, hydroxynefazodone, lubazodone, mepiprazole, nefazodone, triazoledione, trazodone)

Tetracyclic antidepressants (e.g., amoxapine, aptazapine, esmirtazapine, maprotiline, mianserin, mirtazapine)

Tricyclic antidepressants (e.g., amitriptyline)

Typical antipsychotics (e.g., chlorpromazine, fluphenazine, haloperidol, loxapine, perphenazine, pimozide, pipamperone, prochlorperazine, setoperone, spiperone, spiramide, thioridazine, thiothixene, trifluoperazine)

Unknown/unsorted: Ergolines (e.g., dihydroergotamine, nicergoline)

Agonists: 4-Methylaminorex

Amphetamines (e.g., chlorphentermine, cloforex, dexfenfluramine, fenfluramine, levofenfluramine, norfenfluramine)

DOx (e.g., DOB, DOC, DOI, DOM)

Ergolines (e.g., cabergoline, dihydroergocryptine, dihydroergotamine, ergotamine, methylergometrine (methylergonovine), methysergide, pergolide)

MDxx (e.g., MDA (tenamfetamine), MDMA (midomafetamine), MDOH, MMDA)

Piperazines (e.g., TFMPP)

Serotonin (5-HT)

Tryptamines (e.g., 5-BT, 5-CT, 5-MT, α-Me-5-HT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine)

Antagonists: Agomelatine

Atypical antipsychotics (e.g., amisulpride, aripiprazole, asenapine, brexpiprazole, cariprazine, clozapine, N-desalkylquetiapine (norquetiapine), N-desmethylclozapine (norclozapine), olanzapine, pipamperone, quetiapine, risperidone, ziprasidone)

Ergolines (e.g., amesergide, bromocriptine, lisuride, LY-53857, LY-272015, mesulergine)

Metitepine (methiothepin)

Tetracyclic antidepressants (e.g., amoxapine, mianserin, mirtazapine)

Typical antipsychotics (e.g., chlorpromazine)

Unknown/unsorted: Ergolines (e.g., ergometrine (ergonovine))

Agonists: 2Cs (e.g., 2C-B, 2C-E, 2C-I, 2C-T-2, 2C-T-7, 2C-T-21)

5-Methoxytryptamines (5-MeO-DET, 5-MeO-DiPT, 5-MeO-DMT, 5-MeO-DPT, 5-MT)

α-Alkyltryptamines (e.g., 5-Cl-αMT, 5-Fl-αMT, 5-MeO-αET, 5-MeO-αMT, α-Me-5-HT, αET, αMT)

DOx (e.g., DOB, DOC, DOI, DOM)

Ergolines (e.g., ALD-52, cabergoline, dihydroergotamine, ergine (LSA), ergotamine, lisuride, LA-SS-Az, LSB, LSD, LSD-Pip, LSH, LSP, pergolide)

MDxx (e.g., MDA (tenamfetamine), MDMA (midomafetamine), MDOH, MMDA)

Phenethylamines (e.g., lophophine, mescaline)

Piperazines (e.g., aripiprazole, BZP, mCPP, quipazine, TFMPP)

Serotonin (5-HT)

Tryptamines (e.g., 5-BT, 5-CT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine)

Antagonists: Adatanserin

Atypical antipsychotics (e.g., asenapine, clorotepine, clozapine, fluperlapine, iloperidone, melperone, olanzapine, paliperidone, quetiapine, risperidone, sertindole, ziprasidone, zotepine)

Ergolines (e.g., amesergide, bromocriptine, LY-53857, LY-215,840, mesulergine, metergoline, methysergide, sergolexole)

Latrepirdine (dimebolin)

Metitepine (methiothepin)

Tetracyclic antidepressants (e.g., amoxapine, aptazapine, esmirtazapine, maprotiline, mianserin, mirtazapine)

Tricyclic antidepressants (e.g., amitriptyline, nortriptyline)

Typical antipsychotics (e.g., chlorpromazine, loxapine, pimozide, pipamperone, thioridazine)

Unknown/unsorted: Efavirenz

Ergolines (e.g., ergometrine (ergonovine), methylergometrine (methylergonovine))

Agonists: Alcohols (e.g., butanol, ethanol (alcohol), trichloroethanol)

Phenylbiguanide

Piperazines (e.g., BZP, mCPP, quipazine)

Serotonin (5-HT)

Tryptamines (e.g., 2-Me-5-HT, 5-CT, bufotenidine (5-HTQ))

Volatiles/gases (e.g., halothane, isoflurane, toluene, trichloroethane)

Antagonists: Alosetron

Atypical antipsychotics (e.g., clozapine, olanzapine, quetiapine)

Bemesetron (MDL-72222)

Hydroxybupropion

Tetracyclic antidepressants (e.g., amoxapine, mianserin, mirtazapine)

Typical antipsychotics (e.g., loxapine)

Volatiles/gases (e.g., nitrous oxide, sevoflurane, xenon)

Unknown/unsorted: LY-53857

Piperazines (e.g., naphthylpiperazine)

Agonists: 5-MT

Serotonin (5-HT)

Antagonists: GR-113808

Agonists: Ergolines (e.g., 2-Br-LSD (BOL-148), ergotamine, LSD)

Serotonin (5-HT)

Tryptamines (e.g., 5-CT)

Antagonists: Asenapine

Latrepirdine (dimebolin)

Metitepine (methiothepin)

Unknown/unsorted: Ergolines (e.g., metergoline, methysergide)
Piperazines (e.g., naphthylpiperazine)

Agonists: Ergolines (e.g., dihydroergocryptine, dihydroergotamine, ergotamine, lisuride, LSD, mesulergine, metergoline, methysergide)

Serotonin (5-HT)

Tryptamines (e.g., 2-Me-5-HT, 5-BT, 5-CT, 5-MT, Bufotenin, E-6801, E-6837, EMD-386088, EMDT, LY-586713, N-Me-5-HT, ST-1936, tryptamine)

Antagonists: ABT-354

Atypical antipsychotics (e.g., aripiprazole, asenapine, clorotepine, clozapine, fluperlapine, iloperidone, olanzapine, tiospirone)

Latrepirdine (dimebolin)

Metitepine (methiothepin)

Tetracyclic antidepressants (e.g., amoxapine, mianserin)

Tricyclic antidepressants (e.g., amitriptyline, clomipramine, doxepin, nortriptyline)

Typical antipsychotics (e.g., chlorpromazine, loxapine)

Unknown/unsorted: Ergolines (e.g., 2-Br-LSD (BOL-148), bromocriptine, lergotrile, pergolide)

Piperazines (e.g., naphthylpiperazine)

Agonists: 8-OH-DPAT

Ergolines (e.g., LSD)

Serotonin (5-HT)

Triptans (e.g., frovatriptan)

Tryptamines (e.g., 5-CT, 5-MT, bufotenin, N-Me-5-HT)

Antagonists: Atypical antipsychotics (e.g., amisulpride, aripiprazole, asenapine, brexpiprazole, clorotepine, clozapine, fluperlapine, olanzapine, risperidone, sertindole, tiospirone, ziprasidone, zotepine)

Ergolines (e.g., 2-Br-LSD (BOL-148), amesergide, bromocriptine, cabergoline, dihydroergotamine, ergotamine, LY-53857, LY-215,840, mesulergine, metergoline, methysergide, sergolexole)

Metitepine (methiothepin)

Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin, mirtazapine)

Tricyclic antidepressants (e.g., amitriptyline, clomipramine, imipramine)

Typical antipsychotics (e.g., acetophenazine, chlorpromazine, chlorprothixene, fluphenazine, loxapine, pimozide)

Unknown/unsorted: Ergolines (e.g., lisuride, pergolide)

Piperazines (e.g., naphthylpiperazine)

See also: Receptor/signaling modulators

Adrenergics

Dopaminergics

Melatonergics

Monoamine reuptake inhibitors and releasing agents

Monoamine metabolism modulators

Monoamine neurotoxins

1-Methylpsilocin

5,7-Dihydroxytryptamine

5-Methoxytryptamine

5-MeO-7,N,N-TMT

5-(Nonyloxy)tryptamine

6-Hydroxymelatonin

7-Methyl-α-ethyltryptamine

α,N,N-Trimethyltryptamine

Bufotenin (5-HO-DMT)

Convolutindole A

Desformylflustrabromine

Methylbutyltryptamine

N-Ethyltryptamine

N-Feruloylserotonin

N-t-Butyltryptamine

Plakohypaphorine

Psilocin (4-HO-DMT)

Psilocybin (4-PO-DMT)

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