IsoDMT

isoDMT, also known as N,N-dimethylisotryptamine, is a putatively non-hallucinogenic serotonin 5-HT_2A 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]

isoDMT

Clinical data
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
Identifiers
IUPAC name 2-indol-1-yl-N,N-dimethylethanamine
CAS Number	87482-09-5
PubChem CID	15893127
ChemSpider	11597169
ChEMBL	ChEMBL38633
CompTox Dashboard (EPA)	DTXSID80579188
Chemical and physical data
Formula	C12H16N2
Molar mass	188.274 g·mol−1
3D model (JSmol)	Interactive image
SMILES CN(C)CCN1C=CC2=CC=CC=C21
InChI InChI=1S/C12H16N2/c1-13(2)9-10-14-8-7-11-5-3-4-6-12(11)14/h3-8H,9-10H2,1-2H3 Key:PSHKCPACSIZILK-UHFFFAOYSA-N

Pharmacology

The drug 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 (K_i) for the serotonin 5-HT₂ receptors have been reported to be 600–650 nM for 5-HT_2A and 720 nM at 5-HT_2C.^[9]

Analogs

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]

History

isoDMT and its derivatives were first described in the scientific literature by 1984.^[1][8][10] They were subsequently further characterized in 2020.^[7][6]

See also

• 2-Bromo-LSD
• 2ZEDMA
• Ariadne
• C-DMT
• ITI-1549
• Lisuride
• Tabernanthalog