IsoDMT
Serotonergic drug
From Wikipedia, the free encyclopedia
isoDMT, also known as N,N-dimethylisotryptamine, is a putatively non-hallucinogenic serotonin 5-HT2A receptor agonist and psychoplastogen of the isotryptamine group.[1][2][3][4][5][6] It is the isotryptamine homologue of dimethyltryptamine (DMT), a more well-known serotonergic psychedelic of the tryptamine family, and represents a small structural modification of DMT.[2][3][6]
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| Other names | iso-DMT; N,N-Dimethylisotryptamine; iso-N,N-DMT; N,N-Dimethylaminoisotryptamine; Dimethylaminoisotryptamine |
| Drug class | Non-hallucinogenic serotonin 5-HT2A receptor agonist; Psychoplastogen |
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| Formula | C12H16N2 |
| Molar mass | 188.274 g·mol−1 |
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Pharmacology
Pharmacodynamics
isoDMT does not produce hallucinogen-like stimulus generalization in animal drug discrimination tests and similarly does not produce the head-twitch response, an animal behavioral proxy of psychedelic-like effects.[1][2][4][6] As such, it is not expected to be hallucinogenic in humans.[1][2][4][6] However, isoDMT retains significant activity at the serotonin 5-HT2 receptors and shows psychoplastogenic effects comparable to those of serotonergic psychedelics in preclinical research.[7][6][8][9] Its affinities (Ki) for the serotonin 5-HT2 receptors have been reported to be 600–650 nM for 5-HT2A and 720 nM at 5-HT2C.[9]
Chemistry
Analogues
Several derivatives of isoDMT have been developed, including the non-hallucinogenic psychoplastogens 5-MeO-isoDMT and zalsupindole (DLX-001; AAZ-A-154; (R)-5-MeO-α-methyl-isoDMT) and the hallucinogen and psychoplastogen 6-MeO-isoDMT.[1][10][7][6] Zalsupindole has shown antidepressant-like effects in animals, thought to be secondary to its psychoplastogenic actions, and is under development for potential medical use to treat neuropsychiatric disorders like depression.[1][11][12][13] Another analogue of isoDMT is α-methylisotryptamine (isoAMT), the isotryptamine homologue of α-methyltryptamine (AMT).[14][15][16]