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| Other names | O4310; 1-Isopropyl-6-fluoropsilocin |
| Drug class | Serotonin 5-HT2A receptor agonist |
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| Formula | C15H21FN2O |
| Molar mass | 264.344 g·mol−1 |
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O-4310, also known as 1-isopropyl-6-fluoropsilocin, is a serotonin receptor agonist of the tryptamine family. [1] [2] It is the 1-isopropylated and 6-flourinated derivative of the serotonergic psychedelic psilocin. [2]
The drug is said to be a serotonin 5-HT2A receptor agonist and to be highly selective for activation of this receptor over the closely related serotonin 5-HT2B and 5-HT2C receptors. [2] Its EC50 at the serotonin 5-HT2A receptor was reported to be 5 nM and it was said to have an Emax of 89% relative to serotonin. [2] Conversely, O-4310 was said to be inactive at the serotonin 5-HT2B receptor, with no EC50 or Emax reported for this receptor, and was claimed to have an EC50 of 592 nM at the serotonin 5-HT2C receptor with an Emax of approximately 50%. [2] Hence, O-4310 appears to show about 118-fold selectivity for activation of the serotonin 5-HT2A receptor over the serotonin 5-HT2C receptor. [2] The pharmacodynamic activity of O-4310 was briefly described in a patent but not in the published scientific literature. [2] [1] If the reported data are accurate, O-4310, along with other drugs like 25CN-NBOH and (S,S)-DMBMPP, would be one of the most selective known agonists of the serotonin 5-HT2A receptor over the other serotonin 5-HT2 receptors. [3]
O-4310 was patented by Bryan Roth and colleagues in 2006 and the patent was assigned to the American pharmaceutical company Organix Inc as well as a couple of other assignees. [2] The drug was also employed in an animal study and described in the scientific literature by a group of Iranian researchers in 2017. [1]
2,5-Dimethoxy-4-iodoamphetamine (DOI) is a psychedelic drug of the amphetamine and 4-substituted-2,5-dimethoxyamphetamine (DOx) families.
The 5-HT2A receptor is a subtype of the 5-HT2 receptor that belongs to the serotonin receptor family and is a G protein-coupled receptor (GPCR). The 5-HT2A receptor is a cell surface receptor, but has several intracellular locations.
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.
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25B-NBOMe is a derivative of the phenethylamine psychedelic 2C-B, discovered in 2004 by Ralf Heim at the Free University of Berlin. It acts as a potent full agonist for the 5HT2A receptor. Duration of effects lasts about 3–10 hours, although the parent compound is rapidly cleared from the blood when used in the radiolabeled form in tracer doses. Recently, Custodio et al. (2019) evaluated the potential involvement of dysregulated dopaminergic system, neuroadaptation, and brain wave changes which may contribute to the rewarding and reinforcing properties of 25B-NBOMe in rodents.
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5-HT2C receptor agonists are a class of drugs that activate 5-HT2C receptors. They have been investigated for the treatment of a number of conditions including obesity, psychiatric disorders, sexual dysfunction and urinary incontinence.
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DMBMPP, or 2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine, is a 2-benzylpiperidine analog of the hallucinogenic N-benzylphenethylamine 25B-NBOMe and was discovered in 2011 by Jose Juncosa in the group of David E. Nichols at Purdue University. DMBMPP differs from 25B-NBOMe by incorporating the amine within a piperidine ring, making for a more rigid molecular structure than that of the open-chain 25B-NBOMe. The presence of the piperidine ring introduces two stereocenters, thus, four stereoisomers of this compound can be made.
25N-NBOMe is a derivative of the hallucinogen 2C-N. The pharmacological properties of 25N-NBOMe have not been described in the scientific literature, but it is believed to act in a similar manner to related compounds such as 25I-NBOMe and 25C-NBOMe, which are potent agonists at the 5HT2A receptor. 25N-NBOMe has been sold as a street drug and has only been described in the literature in terms of identification by forensic analysis.
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The 25-NB (25x-NBx) series, or NBOMe series, also known as the N-benzylphenethylamines, is a family of serotonergic psychedelics. They are substituted phenethylamines and were derived from the 2C family. The most commonly encountered NBOMe drugs are 25I-NBOMe, 25B-NBOMe, and 25C-NBOMe.
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7-F-5-MeO-MET (5-MeO-7-F-MET, 5-Methoxy-7-fluoro-N-methyl-N-ethyltryptamine) is a tryptamine derivative which acts as a serotonin receptor agonist selective for the 5-HT2 subtypes, with a pEC50 of 8.71 at 5-HT2A, vs 8.25 at 5-HT2B and 7.69 at 5-HT2C. In animal tests it produced the most potent head-twitch response of a range of related fluorinated tryptamine derivatives tested, though still with slightly lower potency than psilocybin.
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Lysergine, also known as 9,10-didehydro-6,8β-dimethylergoline, is an ergot alkaloid and serotonin receptor agonist of the ergoline family. It is a minor constituent of ergot.
ITI-1549 is a putatively non-hallucinogenic serotonin 5-HT2A receptor agonist which is under development for the treatment of mood disorders and other psychiatric disorders. In addition to acting at the serotonin 5-HT2A receptor, it is also an antagonist of the serotonin 5-HT2B receptor and an agonist of the serotonin 5-HT2C receptor. The drug's route of administration has not been specified.
BMB-201 is a serotonin 5-HT2A and 5-HT2C receptor agonist described as a non-hallucinogenic psychoplastogen which is under development for the treatment of depression, anxiety, pain, and other indications.
BMB-202 is a serotonin 5-HT2A receptor agonist and psychedelic hallucinogen which is under development for the treatment of depressive disorders and post-traumatic stress disorder (PTSD). It is taken by mouth. However, BMB-202 has also been evaluated by injection in preclinical studies.
The psychedelic phenethylamines typically exhibit less than 5–10-fold selectivity for 5-HT2A over 5-HT2C receptors.53,54 Notable exceptions include (S,S)-DMBMPP and 25CN-NBOH (Figure 3), which are the most selective 5-HT2AR agonists published to date.49,58–61 (S,S)-DMBMPP exhibits more than 100-fold higher binding affinity for the 5-HT2AR over 5-HT2CR, and 25CN-NBOH has substantially higher agonist potencies at 5-HT2AR compared to 5-HT2CR.
