Ibogaminalog

Chemical compound From Wikipedia, the free encyclopedia

Ibogaminalog (developmental code name DM-506) is a non-selective and non-psychedelic serotonin receptor modulator of the ibogalog group related to the iboga alkaloid ibogamine but with a simplified chemical structure. It was first described in the 1960s but was subsequently further studied and reported on in the 2020s.[1][2][3][4][5][6]

Other namesDM-506; DM506
CAS Number
Quick facts Clinical data, Other names ...
Ibogaminalog
Clinical data
Other namesDM-506; DM506
Drug classNon-selective serotonin receptor modulator; Non-hallucinogenic serotonin 5-HT2A receptor partial agonist
Identifiers
  • 3-methyl-2,4,5,6-tetrahydro-1H-azepino[4,5-b]indole
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H16N2
Molar mass200.285 g·mol−1
3D model (JSmol)
  • CN1CCC2=C(CC1)NC3=CC=CC=C23
  • InChI=1S/C13H16N2/c1-15-8-6-11-10-4-2-3-5-12(10)14-13(11)7-9-15/h2-5,14H,6-9H2,1H3
  • Key:WBCPONKOWIDTJM-UHFFFAOYSA-N
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Pharmacology

Ibogaminalog is known to act as an agonist of serotonin receptors, including of the serotonin 5-HT2A receptor (Ki = 17–11,190 nM; EC50Tooltip half-maximal effective concentration = 2.9–34 nM; EmaxTooltip maximal efficacy = 33–76%), the serotonin 5-HT2B receptor (Ki = 16.5–63,780 nM; EC50 = 2.9–33 nM; Emax = 68–69%), and the serotonin 5-HT6 receptor (EC50 = 2.9 nM; Emax = 96%), and as an inverse agonist of the serotonin 5-HT7 receptor (ImaxTooltip maximal inhibition = 14%).[4][3][7][8]

It is a weak to very weak monoamine reuptake inhibitor, including of serotonin, norepinephrine, and dopamine (IC50Tooltip half-maximal inhibitory concentration = 3,100 nM, 9,500 nM, and 70,000 nM, respectively), whereas it is not a significant monoamine oxidase inhibitor (MAOI) of MAO-A or MAO-B.[7] The drug also acts weakly as a negative allosteric modulator of the α7 and α9α10 nicotinic acetylcholine receptors.[2]

Ibogaminalog does not produce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents, and hence may be non-hallucinogenic in humans.[4] On the other hand, it has been found to produce sedative, antidepressant-like, anxiolytic-like, antiaddictive-like, and analgesic-like effects in rodents.[4][7][5][3]

See also

References

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