DM-506

DM-506
Identifiers
	IUPAC name 3-methyl-2,4,5,6-tetrahydro-1H-azepino[4,5-b]indole;
CAS Number	7546-66-9 ;
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;

DM-506 (Ibogaminalog) is a drug first invented in the 1960s,^[1] which acts as both a partial agonist at the 5-HT_2A receptor, and a negative allosteric modulator at the α7 and α9α10 nicotinic acetylcholine receptors. It can be regarded as a structurally simplified derivative of ibogaine and has been researched both for anti-addictive effects and for the treatment of neuropathic pain.^[2]^[3]^[4]^[5]^[6]

References

^ US 3529062, Renner U, "Indole derivatives as antitussive agents.", issued 15 September 1970, assigned to Novartis Corp.
^ Tae HS, Ortells MO, Yousuf A, Xu SQ, Akk G, Adams DJ, Arias HR (May 2024). "Tabernanthalog and ibogainalog inhibit the α7 and α9α10 nicotinic acetylcholine receptors via different mechanisms and with higher potency than the GABA_A receptor and Ca_V2.2 channel". Biochemical Pharmacology. 223: 116183. doi:10.1016/j.bcp.2024.116183. PMC 11151864. PMID 38580167.
^ Arias HR, Micheli L, Rudin D, Bento O, Borsdorf S, Ciampi C, et al. (June 2024). "Non-hallucinogenic compounds derived from iboga alkaloids alleviate neuropathic and visceral pain in mice through a mechanism involving 5-HT_2A receptor activation". Biomedicine & Pharmacotherapy. 177: 116867. doi:10.1016/j.biopha.2024.116867. PMID 38889634.
^ Arias HR, Rudin D, Hines DJ, Contreras A, Gulsevin A, Manetti D, et al. (March 2024). "The novel non-hallucinogenic compound DM506 (3-methyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole) induces sedative- and anxiolytic-like activity in mice by a mechanism involving 5-HT_2A receptor activation". European Journal of Pharmacology. 966: 176329. doi:10.1016/j.ejphar.2024.176329. hdl:2158/1354752. PMID 38253116.
^ Looschen K, Khatri SN, Maulik M, Salisbury C, Carman AF, Corriveau K, et al. (June 2024). "Novel psychoplastogen DM506 reduces cue-induced heroin-seeking and inhibits tonic GABA currents in the Prelimbic Cortex". Neurochemistry International. 178: 105785. doi:10.1016/j.neuint.2024.105785. hdl:2158/1371513. PMID 38838988.
^ Tae HS, Ortells MO, Tekarli BJ, Manetti D, Romanelli MN, McIntosh JM, et al. (July 2023). "DM506 (3-Methyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole fumarate), a Novel Derivative of Ibogamine, Inhibits α7 and α9α10 Nicotinic Acetylcholine Receptors by Different Allosteric Mechanisms". ACS Chemical Neuroscience. 14 (14): 2537–2547. doi:10.1021/acschemneuro.3c00212. PMID 37386821.

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[1] US 3529062, Renner U, "Indole derivatives as antitussive agents.", issued 15 September 1970, assigned to Novartis Corp.

[2] Tae HS, Ortells MO, Yousuf A, Xu SQ, Akk G, Adams DJ, Arias HR (May 2024). "Tabernanthalog and ibogainalog inhibit the α7 and α9α10 nicotinic acetylcholine receptors via different mechanisms and with higher potency than the GABA_A receptor and Ca_V2.2 channel". Biochemical Pharmacology. 223: 116183. doi:10.1016/j.bcp.2024.116183. PMC 11151864. PMID 38580167.

[3] Arias HR, Micheli L, Rudin D, Bento O, Borsdorf S, Ciampi C, et al. (June 2024). "Non-hallucinogenic compounds derived from iboga alkaloids alleviate neuropathic and visceral pain in mice through a mechanism involving 5-HT_2A receptor activation". Biomedicine & Pharmacotherapy. 177: 116867. doi:10.1016/j.biopha.2024.116867. PMID 38889634.

[4] Arias HR, Rudin D, Hines DJ, Contreras A, Gulsevin A, Manetti D, et al. (March 2024). "The novel non-hallucinogenic compound DM506 (3-methyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole) induces sedative- and anxiolytic-like activity in mice by a mechanism involving 5-HT_2A receptor activation". European Journal of Pharmacology. 966: 176329. doi:10.1016/j.ejphar.2024.176329. hdl:2158/1354752. PMID 38253116.

[5] Looschen K, Khatri SN, Maulik M, Salisbury C, Carman AF, Corriveau K, et al. (June 2024). "Novel psychoplastogen DM506 reduces cue-induced heroin-seeking and inhibits tonic GABA currents in the Prelimbic Cortex". Neurochemistry International. 178: 105785. doi:10.1016/j.neuint.2024.105785. hdl:2158/1371513. PMID 38838988.

[6] Tae HS, Ortells MO, Tekarli BJ, Manetti D, Romanelli MN, McIntosh JM, et al. (July 2023). "DM506 (3-Methyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole fumarate), a Novel Derivative of Ibogamine, Inhibits α7 and α9α10 Nicotinic Acetylcholine Receptors by Different Allosteric Mechanisms". ACS Chemical Neuroscience. 14 (14): 2537–2547. doi:10.1021/acschemneuro.3c00212. PMID 37386821.

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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

DM-506

See also

References