dimethyltryptamine   Click here for help

GtoPdb Ligand ID: 141

Abbreviated name: DMT
Synonyms: N,N-dimethyltryptamine
Compound class: Synthetic organic
Comment: Dimethyltryptamine (DMT) is an hallucinogenic substance with psychoactive effects similar to those of Lysergide (LSD). It occurs in many plants and animals, and is structurally related to tryptamine.
It is the primary indole alkaloid hallucinogen (from Psychotria viridis plants) contained in Ayahuasca.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 19.03
Molecular weight 188.13
XLogP 2.04
No. Lipinski's rules broken 0
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Canonical SMILES CN(CCc1c[nH]c2c1cccc2)C
Isomeric SMILES CN(CCc1c[nH]c2c1cccc2)C
InChI InChI=1S/C12H16N2/c1-14(2)8-7-10-9-13-12-6-4-3-5-11(10)12/h3-6,9,13H,7-8H2,1-2H3
Bioactivity Comments
Orally ingested DMT is centrally active only when combined with a peripheral monoamine oxidase (MAO) inhibitor [3] such as the β-carboline alkaloids harmine or harmaline (exemplified in the psychoactive brew Ayahuasca).
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
5-HT6 receptor Hs Agonist Full agonist 7.2 pKi - 1
pKi 7.2 [1]
5-HT1D receptor Hs Agonist Full agonist 7.0 – 7.3 pKi - 2
pKi 7.0 – 7.3 [2]