2C-iBu
Pharmaceutical compound From Wikipedia, the free encyclopedia
2,5-Dimethoxy-4-isobutylphenethylamine (2C-iBu or 2C-IB), also known by its developmental code name ELE-02, is a serotonin 5-HT2A receptor agonist, serotonergic psychedelic, and anti-inflammatory drug which is under development for the treatment of inflammation.[2][3][4][5][6][7] It is a member of the phenethylamine and 2C families of compounds.[4][5][7] The drug is being developed as a topical eye drop for treatment of inflammatory eye conditions.[2][3] There is also interest in 2C-iBu and related drugs for treatment of systemic inflammation and neuroinflammation.[8][9][10][11][12][5]
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| Clinical data | |
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| Other names | 2,5-Dimethoxy-4-isobutylphenethylamine; 4-Isobutyl-2,5-dimethoxyphenethylamine; 2C-iBu; 2C-IB; ELE-02; ELE02; ELEU02 |
| Routes of administration | Oral;[1] Ophthalmic[2][3] |
| Drug class | Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen; Anti-inflammatory drug |
| Pharmacokinetic data | |
| Protein binding | 74%[4] |
| Duration of action | 20 hours[1] |
| Identifiers | |
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| PubChem CID | |
| Chemical and physical data | |
| Formula | C14H23NO2 |
| Molar mass | 237.343 g·mol−1 |
| 3D model (JSmol) | |
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2C-iBu was not assessed or discovered by Alexander Shulgin and was not described in PiHKAL (Phenethylamines I Have Known and Loved) (1991).[7][13] However, he did include 2C-iBu (as "2C-IB") as a DOM analogue in a table in The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds (2011).[1] In addition, he stated in a footnote that a 5 mg oral dose of 2C-iBu produces threshold activity and has a long duration of about 20 hours.[1] The cited source for these observations, however, was only a 2006 personal communication with "M. Mueller." [1]
2C-iBu was subsequently more thoroughly characterized by Charles D. Nichols and colleagues at Louisiana State University School of Medicine as a novel anti-inflammatory drug in the late 2010s.[4][7] Eleusis has licensed 2C-iBu intellectual property from LSU and the drug has reached the preclinical research stage of development, but no recent development has been reported as of October 2023.[2][3]
Pharmacology
Summarize
Perspective
2C-iBu is a highly potent and robustly efficacious serotonin 5-HT2A receptor agonist.[4] Its EC50 values are 1.3 nM for calcium mobilization and 57.5 nM for β-arrestin-2 recruitment, whereas its Emax values are 103% for calcium mobilization and 77% for β-arrestin-2 recruitment relative to serotonin.[4] The drug showed higher potency and efficacy as a serotonin 5-HT2A receptor agonist than several other 2C drugs, including 2C-NP, 2C-B, 2C-I, 2C-H, and 2C-iP, whereas its activities were more comparable to or less than those of the DOx drugs DOIB, (R)-DOB, (R)-DOI, and DOiP.[4] 2C-iBu has also been assessed and found to bind to other serotonin receptors, including the serotonin 5-HT2C, 5-HT2B, 5-HT1B, 5-HT1D, 5-HT1A, 5-HT7, and 5-HT6 receptors, in that order of affinity and with varying avidities.[4]
2C-iBu dose-dependently produces the head-twitch response (HTR), a behavioral proxy of psychedelic effects, in rodents.[4] In terms of ED50, 2C-iBu is about 3-fold less potent than (R)-DOI in producing the HTR.[4] According to Eleusis, it is expected to have "greatly reduced" psychoactivity or hallucinogenic effects compared to related drugs like other members of the 2C family.[6][14]
The drug is effective in an allergic asthma model in rodents and showed similar potency as (R)-DOI.[4] Due to its reduced potency in producing the HTR but retained anti-inflammatory potency, 2C-iBu is expected to show greater separation between the desired anti-inflammatory and the undesired psychedelic effects in humans compared to (R)-DOI.[4] In contrast to certain other anti-inflammatory drugs like corticosteroids, serotonin 5-HT2A receptor agonists like 2C-iBu are not immunosuppressants.[14]
Chemistry
2C-iBu, also known as 2,5-dimethoxy-4-isobutylphenethylamine, is a phenethylamine and 2C derivative.[4][5][7]
Related drugs to 2C-iBu include 2C-Bu (the butyl analogue), 2C-tBu (the tert-butyl analogue), 2C-sBu (the sec-butyl analogue), and 2C-CPM (the cyclopropylmethyl analogue).[4] In addition, 2C-iBu is related to DOx drugs such as DOIB (DOiBu).[4][15]
According to Charles D. Nichols, 2,5-dimethoxyamphetamine (2,5-DMA) has potent anti-inflammatory activity with weak or no hallucinogenic effects.[7][15] Moreover, DOTFM has potent psychedelic effects with no anti-inflammatory activity.[7][16][17] Hence, it appears that the anti-inflammatory effects and psychedelic effects of serotonin 5-HT2A receptor agonists can be fully dissociated.[7]
The chemical synthesis of 2C-iBu has been described.[4][1]
Clinical development
2C-iBu was developed as a novel anti-inflammatory drug by Charles D. Nichols and colleagues at Eleusis in the late 2010s.[7][4] They are developing it for treatment of inflammatory conditions.[2][3] Eleusis was acquired by and merged into Beckley Psytech in October 2022.[2][18][19] The drug has reached the preclinical research stage of development, but no recent development has been reported as of October 2023.[2][3] Eleusis has licensed intellectual property surrounding 2C-iBu and has patent protection for 2C-iBu.[6][4]
Legal status
2C-iBu is not a controlled substance in the United States as of 2020.[6]
See also
References
External links
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