Ibogaminalog

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]}

Ibogaminalog

Clinical data
Other names	DM-506; DM506
Drug class	Non-selective serotonin receptor modulator; Non-hallucinogenic serotonin 5-HT2A receptor partial agonist
Identifiers
IUPAC name 3-methyl-2,4,5,6-tetrahydro-1H-azepino[4,5-b]indole
CAS Number	7546-66-9 Y
PubChem CID	24183
ChemSpider	22605
CompTox Dashboard (EPA)	DTXSID70226391
Chemical and physical data
Formula	C13H16N2
Molar mass	200.285 g·mol−1
3D model (JSmol)	Interactive image
SMILES CN1CCC2=C(CC1)NC3=CC=CC=C23
InChI 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

Pharmacology

Ibogaminalog is known to act as an agonist of serotonin receptors, including of the serotonin 5-HT_2A receptor (K_i = 17–11,190 nM; EC₅₀Tooltip half-maximal effective concentration = 2.9–34 nM; E_maxTooltip maximal efficacy = 33–76%), the serotonin 5-HT_2B receptor (K_i = 16.5–63,780 nM; EC₅₀ = 2.9–33 nM; E_max = 68–69%), and the serotonin 5-HT₆ receptor (EC₅₀ = 2.9 nM; E_max = 96%), and as an inverse agonist of the serotonin 5-HT₇ receptor (I_maxTooltip 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

• Ibogalog
• Lorcaserin
• PHA-57378
• PNU-22394
• PNU-181731
• Ibogainalog
• Tabernanthalog