4-Fluoro-5-methoxy-DMT

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4-Fluoro-5-methoxy-DMT

Systematic (IUPAC) name
4-Fluoro-5-Methoxy-N,N-dimethyltryptamine
Clinical data
Legal status	?
Identifiers
CAS number	312314-18-4
ATC code	?
Chemical data
Formula	C₁₃H₁₇F N₂O
Mol. mass	236,13 g/mol
Y (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-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]

References

↑ 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.
↑ 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.

Hallucinogens

Psychedelics
5-HT_2AR agonists

Lysergamides	AL-LAD ALD-52 BU-LAD CYP-LAD IP-LAD Diallyllysergamide Dimethyllysergamide Ergometrine ETH-LAD LAE-32 LPD-824 LSA LSD LSD-Pip LSH LSM-775 Lysergic acid 2-butyl amide LSZ Lysergic acid 3-pentyl amide Methylergometrine Methylisopropyllysergamide Methysergide N1-Methyl-lysergic acid diethylamide PARGY-LAD PRO-LAD

Phenethylamines	Aleph 2-Methyl-MDA 2C-B 2C-B-Dragonfly 2C-B-FLY βk-2C-B 2C-C 2C-C-FLY 25C-NBOMe 25CN-NBOH 25CN-NBOMe 25D-NBOMe 2C-D 2C-D-FLY 2C-E 2C-E-FLY 2C-E-NBOMe 2C-EF 2C-F 2C-F-NBOMe 2C-G 2C-G-NBOMe 2C-H-NBOMe 2C-I 2C-I-FLY 2C-N 25N-NBOMe 2C-O 2C-O-4 2C-P 2C-T 2C-T-2 2C-T-4 2C-T-4-NBOMe 2C-T-7 2C-T-7-FLY 2C-T-7-NBOH 2C-T-8 2C-T-13 2C-T-15 2C-T-17 2C-T-19 2C-T-21 2C-TFM 25TFM-NBOMe 2C-YN 2CBCB-NBOMe 2CBFly-NBOMe 2CD-5EtO 25B-NBOMe 25C-NBOH 25I-NBMD 25I-NBOH 25I-NBOMe 2C-P-NBOMe 3C-AL 3C-E 3C-P 5-APB 5-APDB 5-APDI 5-Methyl-MDA 6-APB 6-APDB 6-Methyl-MDA Br-DFLY DESOXY DMMDA DMMDA-2 DOB DOB-FLY DOC DOEF DOET DOF DOI DOM DOM-FLY DON DOPR DOTFM Escaline Ganesha HOT-2 HOT-7 HOT-17 Isoproscaline Jimscaline Juncosamine Lophophine Macromerine MDA MDEA MDMA Mescaline Methallylescaline MMA MMDA MMDA-2 MMDA-3a MMDMA NBOMe-mescaline Proscaline TCB-2 TFMFly TMA

Piperazines	pFPP TMFPP mCPP

Tryptamines	1-Methyl-5-methoxy-diisopropyltryptamine 2,N,N-TMT 4,5-DHP-AMT 4,5-DHP-DMT 4-Acetoxy-DALT 4-Acetoxy-DET 4-Acetoxy-DiPT 4-Acetoxy-DMT 4-Acetoxy-DPT 4-Acetoxy-MiPT 4-HO-5-MeO-DMT 4-HO-DBT 4-HO-DPT 4-HO-MET 4-HO-MPMI 4-HO-MPT 4,N,N-TMT 4-Propionyloxy-DMT 5,6-diBr-DMT 5-AcO-DMT 5-Bromo-DMT 5-Me-MIPT 5-MeO-2,N,N-TMT 5-MeO-4,N,N-TMT 5-MeO-α,N,N-TMT 5-MeO-α-ET 5-MeO-α-MT 5-MeO-DALT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT 5-MeO-DPT 5-MeO-EiPT 5-MeO-MET 5-MeO-MiPT 5-MeO-MPMI 5-N,N-TMT 7,N,N-TMT α-ET α-MT α,N,N-TMT Aeruginascin Baeocystin Bufotenin DALT DBT DCPT DET DIPT DMT DPT EiPT Ethocin Ethocybin Iprocin MET Miprocin MiPT Norbaeocystin PiPT Psilocin Psilocybin

Others	AL-38022A Elemicin Ibogaine Myristicin Noribogaine Voacangine

Dissociatives
NMDAR antagonists

Adamantanes	Amantadine Memantine Rimantadine

Arylcyclohexylamines	3-MeO-PCP 4-MeO-PCP Dieticyclidine Diphenidine Esketamine Ethketamine Eticyclidine Gacyclidine Ketamine Methoxetamine Methoxyketamine Neramexane PCPr Phencyclidine Rolicyclidine Tenocyclidine Tiletamine

Morphinans	Dextrallorphan Dextromethorphan Dextrorphan Racemethorphan Racemorphan

Others	2-MDP 8A-PDHQ Aptiganel Dexoxadrol Dizocilpine Etoxadrol Ibogaine Midafotel NEFA Nitrous oxide Noribogaine Perzinfotel Remacemide Selfotel Xenon

Deliriants
mAChR antagonists

Miscellaneous

Cannabinoids
CB₁R agonists

Phytocannabinoids	Cannabinol THC (Dronabinol) THCV (Cannabidiol has different mechanism of action)

Synthetic	CP 47,497 CP 55,244 CP 55,940 DMHP HU-210 JWH-018 JWH-030 JWH-073 JWH-081 JWH-200 JWH-250 Levonantradol Nabilone Nabitan Parahexyl WIN 55,212-2

D₂R agonists

Aporphine
Bromocriptine
Cabergoline
Lisuride
Memantine
Nuciferine
Pergolide
Piribedil
Pramipexole
Ropinirole
Rotigotine
Also indirect D₂ agonists, such as dopamine reuptake inhibitors (cocaine, methylphenidate), releasing agents (amphetamine, methamphetamine), and precursors (levodopa).

GABA_AR agonists

Inhalants
Mixed MOA

Others

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4-Fluoro-5-methoxy-DMT

See also

References