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// Workers AI · dad joke modeWhat did DMAI say to its date? "You're my data-match

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DMAI
Clinical data
Other namesBD-214; BD214; UCD0076; UCD-0076; 4-DMAEI; 4-(N,N-Dimethylaminoethyl)indole
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor antagonist; Serotonin 5-HT2B receptor agonist; Serotonin 5-HT2C receptor agonist; Dopamine D2 receptor agonist
ATC code
  • None
Identifiers
  • 2-(1H-indol-4-yl)-N,N-dimethylethanamine
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC12H16N2
Molar mass188.274 g·mol−1
3D model (JSmol)
  • CN(C)CCC1=C2C=CNC2=CC=C1
  • InChI=1S/C12H16N2/c1-14(2)9-7-10-4-3-5-12-11(10)6-8-13-12/h3-6,8,13H,7,9H2,1-2H3
  • Key:CUMMXOMCIOVFBY-UHFFFAOYSA-N

DMAI, also known as BD-214, UCD0076, or 4-(N,N-dimethylaminoethyl)indole (4-DMAEI), is a monoamine receptor modulator of the phenethylamine family.[1][2][3][4] It is the positional isomer of the psychedelic drug dimethyltryptamine (DMT) in which the side chain has been moved from the 3 position to the 4 position, making the compound a phenethylamine rather than a tryptamine.[1][2] The drug can also be considered a partial ergoline.[1][2][4]

Pharmacology

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Pharmacodynamics

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DMAI shows weak affinity for the serotonin 5-HT2A receptor (Ki = 1,970 nM).[4] The drug shows no agonism of the serotonin 5-HT2A receptor, instead acting as a weak antagonist of this receptor.[4] It is a partial agonist of the serotonin 5-HT2B receptor, with an EC50Tooltip half-maximal effective concentration of 1,630 nM and an EmaxTooltip maximal efficacy of 44%.[4] In addition, it is a potent high-efficacy partial agonist of the serotonin 5-HT2C receptor, with an EC50 of 334 nM and an Emax of 83%.[4] DMAI is also a high-efficacy agonist of the serotonin 5-HT1 receptors, with EC50 values of approximately 500 to 800 nM (except 134 nM at 5-HT1D) and Emax values of greater than 80%.[4] It is a potent and moderate-efficacy partial agonist of the dopamine D2 receptor, with an EC50 of 588 nM and an Emax of 43%.[4]

In accordance with its lack of serotonin 5-HT2A receptor agonism, DMAI failed to produce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[4] Instead, it suppressed the 5-MeO-DMT-induced head-twitch response and antagonized amphetamine-induced hyperlocomotion, effects suggestive of antipsychotic-like activity.[4] The drug has also been reported to produce sympathomimetic effects in cats, which might be mediated by α1-adrenergic receptor stimulation or α2-adrenergic receptor antagonism.[1] It robustly suppresses prolactin levels in rodents, which is assumed to be due to its dopamine D2 receptor agonism.[2][4]

Chemistry

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The chemical synthesis of DMAI has been described.[2][4] Some analogue of DMAI include DEAI (4-(N,N-diethylaminoethyl)indole; 4-DEAEI; BD-271) and DPAI (4-(N,N-dipropylaminoethyl)indole; 4-DPAEI; 2-desoxo-2-ene-ropinirole; BD-179).[1][2]

History

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DMAI was first described in the scientific literature by 1984.[1][3][2] Subsequently, it was described in greater detail by David E. Olson and colleagues in 2026.[4]

See also

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References

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  1. 1 2 3 4 5 6 Koons JC, Long JP, Cannon JG (December 1984). "In vivo and in vitro dopaminergic effects of three ergoline fragments". Naunyn Schmiedebergs Arch Pharmacol. 328 (2): 180–185. doi:10.1007/BF00512069. PMID 6527705.
  2. 1 2 3 4 5 6 7 Persons, Pe; Mayer, Jp; Nichols, De; Cassady, Jm; Smalstig, Eb; Clemens, Ja (1991). "Preliminary evaluation of 4-(2-N,N-dialkylaminoethyl)indoles as potential dopamine agonists". European Journal of Medicinal Chemistry. 26 (4): 473–475. doi:10.1016/0223-5234(91)90110-9. Retrieved 6 October 2026.
  3. 1 2 Long, J. P.; Bhatnagar, R. K.; Chatterjee, T.; Flynn, J. R.; Cannon, J. G. (23 October 2024). "Inhibition of Cardiac Neurotransmission In Vivo and In Vitro by Structural Analogs of Dopamine". Cardiovascular Function of Peripheral Dopamine Receptors. Boca Raton: CRC Press. p. 103–132. doi:10.1201/9781003573753-6. ISBN 978-1-003-57375-3. Retrieved 6 October 2026.
  4. 1 2 3 4 5 6 7 8 9 10 11 12 13 Basargin AG, Domokosa A, Hennessey JJ, Aarrestad IK, Sambyal R, Khatib YA, Krüger J, Dunlap LE, Carter SJ, Rebek IA, McKee JL, Schalk SS, Liu M, Fettinger JC, Gonzalez MA, Potluri A, Tantillo DJ, Fiehn O, McCorvy JD, Olson DE (September 2026). "Deconstruction of lysergic acid diethylamide". Proceedings of the National Academy of Sciences of the United States of America. 123 (38) e2603412123. doi:10.1073/pnas.2603412123. PMID 42709856.
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