DMT
2-(1H-indol-3-yl)-N,N-dimethylethan-1-amine
Overview
DMT belongs to Psychedelics.
Key safety note: DMT produces an extremely intense but short-lived experience when vaporised or injected (often only minutes) that can be psychologically overwhelming, intense fear, disorientation and complete loss of contact with surroundings, so a safe seated setting and a sober sitter matter.[1][2]
Effects
Subjective effects vary. What a substance feels like depends on dose, individual physiology,
mindset, and setting. The points below describe commonly reported effects, not guaranteed, uniform, or
desirable outcomes.
- Extremely rapid, intense and immersive, when vaporised, effects arrive within seconds and can completely replace the perceived environment
- Exceptionally vivid, reproducible geometric visuals and a frequently reported sense of encountering autonomous 'entities' or other realms, often with a comparatively clear-headed mindset
- Short-lived: a vaporised experience typically lasts only 5–20 minutes, whereas oral ayahuasca lasts around 4–6 hours
Dosing & duration
Harm-reduction note: These are commonly cited reference ranges, not a recommendation or a
“safe” dose. Potency, purity, body chemistry, tolerance, and drug combinations vary widely. Start
low, go slow, wait for full effects before redosing, and never assume an unknown product matches these
figures. Missing data is not evidence of safety.
Vaporised, Insufflated, Oral (with an MAOI), Intravenous. DMT is orally inactive on its own (destroyed by gut and liver MAO) and is only active by mouth when combined with an MAOI: the basis of ayahuasca/pharmahuasca (roughly 35–85 mg DMT with 140–240 mg harmala alkaloids), which then lasts about 4–6+ hours. Vaporised, it is active from a few milligrams with effects arriving within seconds and a total duration of only ~5–20 minutes. Intravenous dosing is used in research. The tiered figures below are for the vaporised route.
Dose ranges
Threshold
~2 mg (vaporised)
Light
10–20 mg (vaporised)
Common
20–40 mg (vaporised)
Strong
40–60 mg (vaporised)
Duration
onset
10–40 s (vaporised)
peak
2–8 min
total
5–20 min (vaporised), 4–6 h oral with MAOI
Chemical & Physical Properties
| Formula | C12H16N2 |
| Molar mass | 188.27 g/mol |
| State | Solid |
| Melting point | 46 °C |
| Boiling point | 60–80 °C |
| Density | Not reported |
| Vapor pressure | Not reported |
| pKa | 8.68 |
| LogP | 2.5 (predicted, XLogP3) |
| Solubility | Freely soluble in dilute acetic and dilute mineral acids |
| Refractive index | Not reported |
Identifiers & Synonyms
| CAS | 61-50-7 |
| CAS (enantiomer) | |
| PubChem CID | 6089 |
| InChIKey | DMULVCHRPCFFGV-UHFFFAOYSA-N |
| 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 |
| SMILES | CN(C)CCC1=CNC2=CC=CC=C21 |
Synonyms
- N,N-Dimethyltryptamine
- DMT
- Dimitri
- Active principle of ayahuasca
Pharmacodynamics & Biochemistry
The archetypal short-acting psychedelic tryptamine and the main psychoactive component of ayahuasca. Most of its effects arise from agonism at the 5-HT2A receptor. It also activates 5-HT1A, 5-HT2C and other serotonin subtypes and the σ1 (sigma-1) receptor, with weaker activity at TAAR1 and the serotonin transporter. At 5-HT2A it behaves as a functionally selective ('biased') agonist, driving Gq signalling without strongly recruiting β-arrestin2, which is thought to underlie its notable lack of tolerance on repeated dosing, unlike most classical psychedelics. It is produced endogenously in mammals (biosynthesised from tryptamine by the enzyme INMT), though the physiological role of endogenous DMT remains unresolved.
Biological targets
- 5-HT2A
- 5-HT1A
- 5-HT2C
Binding & functional measurements
| Target | Measurement | Species |
|---|---|---|
| 5-HT2C receptor | Ki 424 ± 150 nM | Human |
| 5-HT1D receptor | Ki 39 nM | Human |
| 5-HT2A receptor | Ki 237 ± 40 nM | Human |
| 5-HT6 receptor | Ki 68 nM | Human |
| 5-HT1A receptor | Ki 75 ± 20 nM | Human |
| 5-HT7 receptor | Ki 88 nM | Human |
| 5-HT1B receptor | Ki 129 nM | Human |
| H1 receptor | Ki 220 ± 30 nM | Human |
| α2B-adrenoceptor | Ki 258 nM | Human |
| α2C-adrenoceptor | Ki 259 nM | Human |
| D1 receptor | Ki 6,000 ± 900 nM | Human |
| 5-HT1E receptor | Ki 456 nM | Human |
| 5-HT5A receptor | Ki 611 nM | Human |
| I1 imidazoline receptor | Ki 650 nM | Human |
| α1A-adrenoceptor | Ki 1,300 ± 200 nM | Human |
| Serotonin transporter | Ki 6,000 ± 600 nM | Human |
| σ1 receptor | Ki 5,209 nM | Human |
| 5-HT2A receptor | EC50 76 ± 30 nM Emax 40 ± 11% | Human |
| 5-HT2B receptor | EC50 3,400 ± 3,200 nM Emax 19 ± 6% | Human |
| D2 receptor | Ki 3,000 ± 400 nM | Human |
| D3 receptor | Ki 6,300 ± 2,100 nM | Human |
| Noradrenaline transporter | Ki 6,500 ± 1,300 nM | Human |
| TAAR1 | Ki 3,300 ± 400 nM | Mouse |
| TAAR1 | Ki 2,200 ± 200 nM | Rat |
| α2-adrenoceptor | Ki 2,100 ± 400 nM | Human |
Pharmacokinetics
| Bioavailability | Orally inactive alone (degraded by MAO-A), active with an MAOI (ayahuasca) |
| Tmax | Smoked/IV: seconds–minutes |
| Half-life | Very short (minutes) |
| Vd | Not reported |
| Protein binding | Not reported |
| Metabolism | Rapid oxidative deamination by monoamine oxidase A |
| Excretion | Renal (metabolites) |
Toxicology & Safety
Harm-reduction note: Toxicity and risk depend on dose, route, purity, combinations, setting, and individual
health factors. Missing harms should never be interpreted as evidence of safety.
Not reported
DMT produces an extremely intense but short-lived experience when vaporised or injected (often only minutes) that can be psychologically overwhelming, intense fear, disorientation and complete loss of contact with surroundings, so a safe seated setting and a sober sitter matter. It raises blood pressure and heart rate. The main added danger is the oral/ayahuasca route: pairing DMT with an MAOI removes MAO protection, so tyramine-rich foods and especially serotonergic drugs (SSRIs, SNRIs, other MAOIs, some triptans, tramadol) can trigger dangerous hypertensive or serotonin-toxicity reactions. Vomiting is common. Its short duration and unusual lack of classical tolerance do not make it low-risk. Limited data must never be read as evidence of safety.[1][2]
Legal Status
Legal note: Legal status can change over time and may vary by country, region, formulation, analogue status,
prescription context, and enforcement practice. Always confirm with current official sources before relying on this section.
US: Schedule I. UK: Class A. DE: BtMG Anlage I
Interactions & Contraindications
Drug interactions
MAOIs Make oral DMT active and greatly prolong its effects, but remove MAO protection, raising the risk of hypertensive and serotonin-toxicity reactions.
SSRIs, SNRIs, Lithium, Tramadol Raise the risk of serotonin toxicity and, with MAOIs, seizures, especially relevant to the ayahuasca route.
Stimulants (amphetamines, cocaine) Add cardiovascular strain and anxiety.
Cannabis Can unpredictably intensify effects and increase anxiety or panic.
Contraindications
Personal or family history of psychosis, schizophrenia or bipolar disorder
Cardiovascular disease, hypertension or arrhythmia significant disease or uncontrolled hypertension.
Concurrent MAOI, SSRI/SNRI or other serotonergic medication particularly with MAOI (ayahuasca) combinations.
Pregnancy or breastfeeding
No interactions or contraindications listed.
Usage & Context
- Research.
- Traditional.
- Recreational.
Sources & Evidence
- Barker SA (2018). N, N-Dimethyltryptamine (DMT), an Endogenous Hallucinogen: Past, Present, and Future Research to Determine Its Role and Function. Front Neurosci 12:536.
PMID 30127713 · doi:10.3389/fnins.2018.00536
- Cameron LP, Olson DE (2018). Dark Classics in Chemical Neuroscience: N, N-Dimethyltryptamine (DMT). ACS Chem Neurosci 9:2344-2357.
PMID 30036036 · doi:10.1021/acschemneuro.8b00101
- Nichols DE (2016). Psychedelics. Pharmacol Rev 68:264-355.
PMID 26841800 · doi:10.1124/pr.115.011478
- PsychonautWiki: DMT (dosage, duration & effects) CC BY-SA 4.0
- Wikipedia: N,N-Dimethyltryptamine CC BY-SA 4.0
- Rickli A, Moning OD, Hoener MC, et al. (2016). Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens. Eur Neuropsychopharmacol 26:1327-37.
PMID 27216487 · doi:10.1016/j.euroneuro.2016.05.001
- PubChem (experimental properties)