FT-104

Last updated

FT-104
RE104.svg
Clinical data
Other namesRE-104; RE104; 4-glutaryloxy-N,N-diisopropyltryptamine
Legal status
Legal status
  • Investigational
Identifiers
  • 1-[3-[2-[Bis(1-methylethyl)amino]ethyl]-1H-indol-4-yl] pentanedioate
CAS Number
PubChem CID
UNII
Chemical and physical data
Formula C21H30N2O
Molar mass 326.484 g·mol−1
3D model (JSmol)
  • CC(C)N(CCC1=CNC2=C1C(=CC=C2)OC(=O)CCCC(=O)O)C(C)C
  • InChI=1S/C21H30N2O4/c1-14(2)23(15(3)4)12-11-16-13-22-17-7-5-8-18(21(16)17)27-20(26)10-6-9-19(24)25/h5,7-8,13-15,22H,6,9-12H2,1-4H3,(H,24,25)
  • Key:LSDOIAGGRBGDJJ-UHFFFAOYSA-N

FT-104 (also known as RE-104 and 4-glutaryloxy-N,N-diisopropyltryptamine) is a psychedelic tryptamine derivative which is a prodrug ester of the well known designer drug 4-HO-DiPT. [1] It is one of a number of related derivatives developed for potential medical applications, and is in human clinical trials as a possible treatment for postpartum depression and treatment-resistant depression. [2] [3] [4] [5]

Contents

It is being developed by the pharmaceutical company Reunion Neuroscience. [6]  As of 2024, FT-104 is entering Phase II clinical trials for post-partum depression. [7]

Pharmacology

FT-104 is a prodrug that is converted into the psychedelic tryptamine 4-HO-DiPT upon administration. [1] [8]  4-OH-DiPT then acts as an agonist on the serotonin 2A receptor which leads to an antidepressant effect. [6]

See also

Related Research Articles

<span class="mw-page-title-main">Psychedelic drug</span> Hallucinogenic class of psychoactive drug

Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary mental states and a perceived "expansion of consciousness". Also referred to as classic hallucinogens or serotonergic hallucinogens, the term psychedelic is sometimes used more broadly to include various types of hallucinogens, such as those which are atypical or adjacent to psychedelia like salvia and MDMA, respectively.

α-Methyltryptamine Chemical compound

α-Methyltryptamine is a psychedelic, stimulant, and entactogen drug of the tryptamine family. It was originally developed as an antidepressant at Upjohn in the 1960s, and was used briefly as an antidepressant in the Soviet Union under the brand name Indopan or Indopane before being discontinued.

<span class="mw-page-title-main">Tryptamine</span> Metabolite of the amino acid tryptophan

Tryptamine is an indolamine metabolite of the essential amino acid tryptophan. The chemical structure is defined by an indole—a fused benzene and pyrrole ring, and a 2-aminoethyl group at the second carbon. The structure of tryptamine is a shared feature of certain aminergic neuromodulators including melatonin, serotonin, bufotenin and psychedelic derivatives such as dimethyltryptamine (DMT), psilocybin, psilocin and others.

<span class="mw-page-title-main">5-MeO-DMT</span> Chemical compound

5-MeO-DMT (5-methoxy-N,N-dimethyltryptamine), also known as O-methylbufotenin or mebufotenin, is a naturally occurring psychedelic of the tryptamine family. It is found in a wide variety of plant species, and is also secreted by the glands of at least one toad species, the Colorado River toad. It may occur naturally in humans as well. Like its close relatives dimethyltryptamine (DMT) and bufotenin (5-HO-DMT), it has been used as an entheogen in South America. Slang terms include Five-methoxy, the power, bufo, and toad venom.

<span class="mw-page-title-main">5-MeO-DiPT</span> Psychedelic tryptamine

5-Methoxy-N,N-diisopropyltryptamine is a psychedelic tryptamine and the methoxy derivative of diisopropyltryptamine (DiPT).

<span class="mw-page-title-main">5-Hydroxytryptophan</span> Chemical compound

5-Hydroxytryptophan (5-HTP), used medically as oxitriptan, is a naturally occurring amino acid and chemical precursor as well as a metabolic intermediate in the biosynthesis of the neurotransmitter serotonin.

α-Ethyltryptamine Chemical compound

α-Ethyltryptamine, also known as etryptamine, is an entactogen and stimulant drug of the tryptamine family. It was originally developed and marketed as an antidepressant under the brand name Monase by Upjohn in the 1960s before being withdrawn due to toxicity.

<span class="mw-page-title-main">4-HO-DiPT</span> Chemical compound

4-Hydroxy-N,N-diisopropyltryptamine is a synthetic psychedelic drug. It is a higher homologue of psilocin, 4-HO-DET, and is a positional isomer of 4-HO-DPT and has a tryptamine molecular sub-structure.

<span class="mw-page-title-main">DiPT</span> Chemical compound

Diisopropyltryptamine is a psychedelic hallucinogenic drug of the tryptamine family that has a unique effect. While the majority of hallucinogens affect the visual sense, DiPT is primarily aural.

<span class="mw-page-title-main">5-MeO-MiPT</span> Chemical compound

5-MeO-MiPT is a psychedelic and hallucinogen of the tryptamine family. It used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs 5-MeO-DiPT, DiPT, and MiPT. It is commonly used as a "substitute" for 5-MeO-DiPT because of the very similar structure and effects.

<span class="mw-page-title-main">Serotonin receptor agonist</span> Neurotransmission-modulating substance

A serotonin receptor agonist is an agonist of one or more serotonin receptors. They activate serotonin receptors in a manner similar to that of serotonin, a neurotransmitter and hormone and the endogenous ligand of the serotonin receptors.

<span class="mw-page-title-main">Substituted tryptamine</span> Class of indoles

Substituted tryptamines, or simply tryptamines, also known as serotonin analogues (i.e., 5-hydroxytryptamine analogues), are organic compounds which may be thought of as being derived from tryptamine itself. The molecular structures of all tryptamines contain an indole ring, joined to an amino (NH2) group via an ethyl (−CH2–CH2−) sidechain. In substituted tryptamines, the indole ring, sidechain, and/or amino group are modified by substituting another group for one of the hydrogen (H) atoms.

<span class="mw-page-title-main">4-PrO-DMT</span> Chemical compound

4-Propionoxy-N,N-dimethyltryptamine is a synthetic psychedelic drug from the tryptamine family with psychedelic effects, and is believed to act as a prodrug for psilocin. It produces a head-twitch response in mice. It has been sold online as a designer drug since May 2019. It was first identified as a new psychoactive substance in Sweden, in July 2019. A number of related derivatives have been synthesized as prodrugs of psilocin for medical applications.

Psychoplastogens are a group of small molecule drugs that produce rapid and sustained effects on neuronal structure and function, intended to manifest therapeutic benefit after a single administration. Several existing psychoplastogens have been identified and their therapeutic effects demonstrated; several are presently at various stages of development as medications including ketamine, MDMA, scopolamine, and the serotonergic psychedelics, including LSD, psilocin, DMT, and 5-MeO-DMT. Compounds of this sort are being explored as therapeutics for a variety of brain disorders including depression, addiction, and PTSD. The ability to rapidly promote neuronal changes via mechanisms of neuroplasticity was recently discovered as the common therapeutic activity and mechanism of action.

<i>O</i>-Acetylbufotenine Psychedelic tryptamine

O-Acetylbufotenine, or bufotenine O-acetate, also known as 5-acetoxy-N,N-dimethyltryptamine (5-AcO-DMT) or O-acetyl-N,N-dimethylserotonin, is a synthetic tryptamine derivative and putative serotonergic psychedelic. It is the O-acetylated analogue of the naturally occurring peripherally selective serotonergic tryptamine bufotenine and is thought to act as a centrally penetrant prodrug of bufotenine.

<span class="mw-page-title-main">5-Fluoro-EPT</span> Chemical compound

5-Fluoro-EPT (5F-EPT, 5-fluoro-N-ethyl-N-propyltryptamine) is a psychedelic tryptamine derivative related to drugs such as EPT and 5-MeO-EPT. It acts as a potent full agonist at the 5-HT2A receptor with an EC50 of 5.54 nM and an efficacy of 104% (compared to serotonin). It produces a head-twitch response in animal studies, and is claimed to have antidepressant activity.

<span class="mw-page-title-main">4-Hydroxytryptamine</span> Serotonin receptor agonist

4-Hydroxytryptamine, also known as N,N-didesmethylpsilocin, is a naturally occurring tryptamine alkaloid. It is closely related chemically to the neurotransmitter serotonin, the psychedelic psilocin, and is the active form of the tryptamine alkaloid norbaeocystin.

MSP-1014 is a serotonergic psychedelic which is under development for the treatment of major depressive disorder, other depressive disorders, and anxiety disorders.

References

  1. 1 2 Bryson N, Alexander R, Asnis-Alibozek A, Ehlers MD (June 2024). "RE104: Synthesis and Activity of a Novel Serotonergic Psychedelic Prodrug of 4-Hydroxy-N,N-diisopropyltryptamine". ACS Chemical Neuroscience. 15 (12): 2386–2395. doi:10.1021/acschemneuro.4c00058. PMC   11191588 . PMID   38758589.
  2. Hallifax J (11 August 2022). "An Inside Look into Field Trip's Next-Generation Psychedelic, FT-104".
  3. WO 2022/000091,Bryson N,"Tryptamine prodrugs",published 6 January 2022, assigned to Field Trip Psychedelics Inc.
  4. US 2022/0024956,Slassi A, Araujo J,"Psilocin derivatives as serotonergic psychedelic agents for the treatment of CNS disorders.",published 27 January 2022, assigned to Mindset Pharma Inc.
  5. WO 2022/246572,Slassi A, Araujo J, Higgin GH, Gabriele J,"Hallucinogen-Fatty Acid Combination",published 1 December 2022, assigned to Mindset Pharma Inc.
  6. 1 2 Braner S (May 8, 2024). "Reunion Neuroscience raises $103 million for a psychedelic to treat depression". Chemical & Engineering News .
  7. Alexander R, Hocevar-Trnka J (June 26, 2024). "RE104: A Novel, Fast-Acting Psychedelic for Postpartum Depression". psychiatrictimes.com.
  8. "Reunion Neuroscience Announces Publication of Results from Early Preclinical Studies Demonstrating the Potential of RE104 for Development in Depressive Disorders". GlobalNewswire. May 20, 2024 via Yahoo!Finance.