6-Fluoro-DMT

Last updated
6-Fluoro-DMT
6-Fluoro-DMT skeletal.svg
Clinical data
ATC code
  • none
Identifiers
  • 2-(6-fluoro-1H-indol-3-yl)-N,N-dimethyl-ethanamine
CAS Number
ChemSpider
Chemical and physical data
Formula C12H15FN2
Molar mass 206.264 g·mol−1
3D model (JSmol)
  • CN(CCC1=CNC2=C1C=CC(F)=C2)C
  • InChI=1S/C12H15FN2/c1-15(2)6-5-9-8-14-12-7-10(13)3-4-11(9)12/h3-4,7-8,14H,5-6H2,1-2H3 Yes check.svgY
  • Key:DZXZPVGWRZCXDH-UHFFFAOYSA-N Yes check.svgY
   (verify)

6-Fluoro-N,N-dimethyltryptamine (6-Fluoro-DMT) is a synthetic drug of the tryptamine chemical class.

Contents

Pharmacology

Binding profile

6-Fluoro-DMT possess affinity for the 5-HT1A (392.6 nM), 5-HT1B (217.7 nM), 5-HT1D (55.4 nM), 5-HT1E (460.8 nM), 5-HT2A (866 nM), 5-HT2B (29.8 nM), 5-HT2C (674.2 nM), 5-HT5A (960.5 nM), 5-HT6 (25.6 nM), 5-HT7 (40.8 nM), D1 (547.3 nM), D2 (610.4 nM), D3 (866.8 nM), D4 (1,454 nM), D5 (6,291 nM), α1A-adrenergic (173.3 nM), α2B-adrenergic (295.5 nM), α2C-adrenergic (148.8 nM), H1 (46.6 nM), H2 (925.4 nM), I1 (898.4 nM), 1 (6,892 nM), and 2 (7,128 nM) receptors, as well as the SERT (144.6 nM). [1] It has low/negligible (> 10,000 nM) affinity for the 5-HT3, α1B-adrenergic, α2A-adrenergic, β1-adrenergic, β2-adrenergic, H3, H4, and M1-M5 receptors, as well as the DAT and NET. [1] It has not been screened at 5-HT1F, 5-HT4, α1D-adrenergic, β3-adrenergic, or VMAT1/VMAT2.

See also

Related Research Articles

2,5-Dimethoxy-4-bromoamphetamine Chemical compound

Dimethoxybromoamphetamine (DOB), also known as brolamfetamine (INN) and bromo-DMA, is a psychedelic drug and substituted amphetamine of the phenethylamine class of compounds. DOB was first synthesized by Alexander Shulgin in 1967. Its synthesis and effects are documented in Shulgin's book PiHKAL: A Chemical Love Story.

3,4-Methylenedioxyamphetamine Empathogen-entactogen, psychostimulant, and psychedelic drug of the amphetamine family

3,4-Methylenedioxyamphetamine is an empathogen-entactogen, psychostimulant, and psychedelic drug of the amphetamine family that is encountered mainly as a recreational drug. In terms of pharmacology, MDA acts most importantly as a serotonin–norepinephrine–dopamine releasing agent (SNDRA). In most countries, the drug is a controlled substance and its possession and sale are illegal.

Carvedilol Oral blood-pressure medication

Carvedilol, sold under the brand name Coreg among others, is a medication used to treat high blood pressure, congestive heart failure (CHF), and left ventricular dysfunction in people who are otherwise stable. For high blood pressure, it is generally a second-line treatment. It is taken by mouth.

Ritanserin

Ritanserin is a serotonin receptor antagonist which was never marketed for clinical use but has been used in scientific research.

Lisuride Chemical compound

Lisuride, sold under the brand name Dopergin among others, is a monoaminergic medication of the ergoline class which is used in the treatment of Parkinson's disease, migraine, and high prolactin levels. It is taken by mouth.

Rotigotine Chemical compound

Rotigotine, sold under the brand name Neupro among others, is a dopamine agonist of the non-ergoline class of medications indicated for the treatment of Parkinson's disease (PD) and restless legs syndrome (RLS). It is formulated as a once-daily transdermal patch which provides a slow and constant supply of the drug over the course of 24 hours.

The alpha-2 (α2) adrenergic receptor is a G protein-coupled receptor (GPCR) associated with the Gi heterotrimeric G-protein. It consists of three highly homologous subtypes, including α2A-, α2B-, and α2C-adrenergic. Some species other than humans express a fourth α2D-adrenergic receptor as well. Catecholamines like norepinephrine (noradrenaline) and epinephrine (adrenaline) signal through the α2-adrenergic receptor in the central and peripheral nervous systems.

Niaprazine

Niaprazine (INN) is a sedative-hypnotic drug of the phenylpiperazine group. It has been used in the treatment of sleep disturbances since the early 1970s in several European countries including France, Italy, and Luxembourg. It is commonly used with children and adolescents on account of its favorable safety and tolerability profile and lack of abuse potential.

2,5-Dimethoxy-4-ethoxyamphetamine Psychedelic drug

2,5-Dimethoxy-4-ethoxyamphetamine (MEM) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin. In his book PiHKAL, he lists the active dose range as 20–50 mg, and the duration as 10–14 hours. According to Shulgin, MEM produces color enhancement, visual phenomena, and pattern movement, among other effects.

5-Bromo-DMT Chemical compound

5-Bromo-DMT (5-bromo-N,N-dimethyltryptamine) is a psychedelic brominated indole alkaloid found in the sponges Smenospongia aurea and Smenospongia echina, as well as in Verongula rigida alongside 5,6-Dibromo-DMT and seven other alkaloids. It is the 5-bromo derivative of DMT, a psychedelic found in many plants and animals.

Tandospirone

Tandospirone is an anxiolytic and antidepressant drug used in China and Japan, where it is marketed by Dainippon Sumitomo Pharma. It is a member of the azapirone class of drugs and is closely related to other azapirones like buspirone and gepirone.

5-Fluoro-AMT Chemical compound

5-Fluoro-α-methyltryptamine, also known as PAL-544, is a putative stimulant, entactogen, and psychedelic tryptamine derivative related to α-methyltryptamine (αMT). It has been found to act as a well-balanced serotonin-norepinephrine-dopamine releasing agent, a 5-HT2A receptor agonist, and a potent and specific MAO-A inhibitor. It produces a strong head-twitch response in mice, and this effect is known to correlate with psychedelic effects in humans, which suggests that 5-fluoro-αMT could be an active psychedelic in humans, although it is not known to have been tested in humans and could be dangerous due to its strong inhibition of MAO-A.

5-HT<sub>2B</sub> receptor Mammalian protein found in Homo sapiens

5-Hydroxytryptamine receptor 2B (5-HT2B) also known as serotonin receptor 2B is a protein that in humans is encoded by the HTR2B gene. 5-HT2B is a member of the 5-HT2 receptor family that binds the neurotransmitter serotonin (5-hydroxytryptamine, 5-HT).

Blonanserin Atypical antipsychotic

Blonanserin, sold under the brand name Lonasen, is a relatively new atypical antipsychotic commercialized by Dainippon Sumitomo Pharma in Japan and Korea for the treatment of schizophrenia. Relative to many other antipsychotics, blonanserin has an improved tolerability profile, lacking side effects such as extrapyramidal symptoms, excessive sedation, or hypotension. As with many second-generation (atypical) antipsychotics it is significantly more efficacious in the treatment of the negative symptoms of schizophrenia compared to first-generation (typical) antipsychotics such as haloperidol.

Quinupramine

Quinupramine is a tricyclic antidepressant (TCA) used in Europe for the treatment of depression.

5-Fluoro-DMT Chemical compound

5-Fluoro-N,N-dimethyltryptamine is a tryptamine derivative related to compounds such as 5-bromo-DMT and 5-MeO-DMT. Fluorination of psychedelic tryptamines either reduces or has little effect on 5-HT2A/C receptor affinity or intrinsic activity, although 6-fluoro-DET is inactive as a psychedelic despite acting as a 5-HT2A agonist, while 4-fluoro-5-methoxy-DMT is a much stronger agonist at 5-HT1A than 5-HT2A.

4C-T-2 Chemical compound

2,5-Dimethoxy-4-ethylthio-α-ethylphenethylamine (4C-T-2) is a synthetic drug of the phenethylamine chemical class. It is the α-ethylated analogue of 2C-T-2.

7,N,N-TMT

7,N,N-trimethyltryptamine (7-methyl-DMT, 7-TMT), is a tryptamine derivative which acts as an agonist of 5-HT2 receptors. In animal tests, both 7-TMT and its 5-methoxy derivative 5-MeO-7-TMT produced behavioural responses similar to those of psychedelic drugs such as DMT, but the larger 7-ethyl and 7-bromo derivatives of DMT did not produce psychedelic responses despite having higher 5-HT2 receptor affinity in vitro (cf. DOBU, DOAM). 7-TMT also weakly inhibits reuptake of serotonin but with little effect on dopamine or noradrenaline reuptake.

5-Chloro-αMT Chemical compound

5-Chloro-α-methyltryptamine (5-Chloro-αMT), also known as PAL-542, is a tryptamine derivative related to α-methyltryptamine (αMT) and one of only a few known specific serotonin-dopamine releasing agents (SDRAs). It has been investigated in animals as a potential treatment for cocaine dependence. The EC50 values of 5-chloro-αMT in evoking the in vitro release of serotonin (5-HT), dopamine (DA), and norepinephrine (NE) in rat synaptosomes were reported as 16 nM, 54 nM, and 3434 nM, with an NE/DA ratio of 63.6 and a DA/5-HT ratio of 3.38, indicating that it is a highly specific and well-balanced SDRA. However, 5-chloro-αMT has also been found to act as a potent full agonist of the 5-HT2A receptor, with an EC50 value of 6.27 nM and an efficacy of 105%, and almost assuredly acts as a potent agonist of other serotonin receptors as well.

Amesergide

Amesergide is a serotonin receptor antagonist of the ergoline and lysergamide families related to methysergide which was under development by Eli Lilly and Company for the treatment of a variety of conditions including depression, anxiety, schizophrenia, male sexual dysfunction, migraine, and thrombosis but was never marketed. It reached phase II clinical trials for the treatment of depression, erectile dysfunction, and premature ejaculation prior to the discontinuation of its development.

References

  1. 1 2 Ray TS (February 2010). "Psychedelics and the human receptorome". PLOS ONE. 5 (2): e9019. Bibcode:2010PLoSO...5.9019R. doi: 10.1371/journal.pone.0009019 . PMC   2814854 . PMID   20126400.