5-MeO-DMT
2-(5-methoxy-1H-indol-3-yl)-N,N-dimethylethan-1-amine
Overview
5-MeO-DMT belongs to Psychedelics / Tryptamines.
Key safety note: 5-MeO-DMT is an exceptionally potent, fast-acting psychedelic, an estimated 4–20× stronger than DMT, with a narrow margin for error, especially when vaporised as the freebase.[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, often overwhelming onset when vaporised: sometimes within seconds
- An 'atypical' psychedelic with relatively few visual effects. The peak is often described as a content-free 'whiteout', ego dissolution or a sense of unity
- Higher rates of fear, anxiety and confusion than most classic psychedelics
- Very short when vaporised (minutes). Much longer when insufflated or taken orally with an MAOI
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/smoked, Insufflated, Oral (with MAOI). 5-MeO-DMT is extremely potent (~4–5× DMT) and very fast-acting. It is most often vaporised as the freebase, where doses are very small and easily miscounted. Insufflated doses are higher and last longer. Oral activity requires an MAOI, which sharply increases the risk of serotonin toxicity: a combination implicated in deaths.
Dose ranges
Vaporised: light
3–6 mg
Vaporised: common
6–12 mg
Vaporised: strong
12–20 mg
Insufflated: common
8–15 mg
Oral + MAOI
10–25 mg (with harmala 70–150 mg)
Duration
onset
5–60 s vaporised, 1–10 min insufflated
peak
5–15 min (vaporised)
total
20–40 min vaporised, 2–3 h insufflated, 3–4 h oral+MAOI
Chemical & Physical Properties
| Formula | C13H18N2O |
| Molar mass | 218.3 g/mol |
| State | Solid |
| Melting point | Not reported |
| Boiling point | Not reported |
| Density | Not reported |
| Vapor pressure | Not reported |
| pKa | Not reported |
| LogP | 1.5 (predicted, XLogP3) |
| Solubility | >32.7 [µg/mL] (The mean of the results at pH 7.4) |
| Refractive index | Not reported |
Identifiers & Synonyms
| CAS | 1019-45-0 |
| CAS (enantiomer) | |
| PubChem CID | 1832 |
| InChIKey | ZSTKHSQDNIGFLM-UHFFFAOYSA-N |
| InChI | InChI=1S/C13H18N2O/c1-15(2)7-6-10-9-14-13-5-4-11(16-3)8-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3 |
| SMILES | CN(C)CCC1=CNC2=C1C=C(C=C2)OC |
Synonyms
- 5-Methoxy-N,N-dimethyltryptamine
- 5-Methoxy-N,N-DMT
- 5-MeO-DMT
- 5-OMe-DMT
- O-Methylbufotenin
- Mebufotenin
- Methylbufotenin
- N,N,O-Trimethylserotonin
- MDMT
- Toad venom (Bufo alvarius)
- Bufo
Pharmacodynamics & Biochemistry
Serotonergic tryptamine psychedelic and a potent, relatively non-selective serotonin receptor agonist. Unusually for a classic psychedelic its highest affinity is at 5-HT1A rather than 5-HT2A, and strong 5-HT1A activation shapes its distinctive, often 'content-free' effects. Also a high-efficacy 5-HT2A agonist (the target most associated with psychedelic effects, at which it is roughly 10× more potent than DMT) and binds many other 5-HT subtypes, the melatonin MT1/MT2 receptors and adrenergic receptors. Rapidly metabolised by monoamine oxidase A and O-demethylated by CYP2D6 to the active metabolite bufotenin. MAO inhibitors dramatically prolong and intensify its effects and create serious toxicity risk. Estimated 4–20× more potent than DMT in humans.
Biological targets
- 5-HT1A
- 5-HT2A
Binding & functional measurements
| Target | Measurement | Species |
|---|---|---|
| 5-HT1D receptor | Ki 2.3 nM | Human |
| 5-HT7 receptor | Ki 3.9 nM | Human |
| 5-HT6 receptor | Ki 6.5 nM | Human |
| 5-HT1B receptor | Ki 14 nM | Human |
| MT2 melatonin receptor | Ki 16 nM | Human |
| 5-HT1F receptor | Ki 37 nM | Human |
| D1 receptor | Ki 80 nM | Human |
| α2C-adrenoceptor | Ki 206 nM | Human |
| MT1 melatonin receptor | Ki 210 nM | Human |
| 5-HT5A receptor | Ki 277 nM | Human |
| 5-HT1E receptor | Ki 360 nM | Human |
| α2B-adrenoceptor | Ki 430 nM | Human |
| α2A-adrenoceptor | Ki 574 nM | Human |
| Serotonin transporter | Ki 2,032 nM | Human |
| α1B-adrenoceptor | Ki 2,188 nM | Human |
| Noradrenaline transporter | Ki 2,859 nM | Human |
| α1A-adrenoceptor | Ki 4,373 nM | Human |
| 5-HT1A receptor | EC50 3.4 nM Emax 115% | Human |
| 5-HT1A receptor | EC50 5.6 nM Emax 107% | Mouse |
| 5-HT2A receptor | EC50 8.9 nM Emax 95.3% | Human |
| 5-HT2A receptor | EC50 48 nM Emax 91.6% | Mouse |
| 5-HT2B receptor | EC50 11 nM Emax 73% | Human |
| 5-HT2C receptor | EC50 7.1 nM Emax 92.3% | Human |
Pharmacokinetics
| Bioavailability | Inhaled/insufflated, orally active only with MAOI |
| Tmax | Smoked: seconds–minutes |
| Half-life | Short (minutes) |
| Vd | Not reported |
| Protein binding | Not reported |
| Metabolism | Oxidative deamination by MAO-A. O-demethylation to bufotenine |
| Excretion | Renal |
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
5-MeO-DMT is an exceptionally potent, fast-acting psychedelic, an estimated 4–20× stronger than DMT, with a narrow margin for error, especially when vaporised as the freebase. It produces markedly higher rates of fear, anxiety and overwhelming 'whiteout' experiences than psychedelics such as LSD, psilocybin, mescaline or DMT, and physical effects can include vomiting, tachycardia, hypertension and, at high doses, loss of consciousness and respiratory compromise. The greatest single danger is combination with monoamine oxidase inhibitors, including the harmala alkaloids in some ceremonial and ayahuasca-style preparations, which sharply raise and prolong 5-MeO-DMT levels. Such combinations have caused serotonin toxicity and death. Deaths have been reported and the human lethal dose is unknown. Material obtained from toad (Incilius/Bufo alvarius) secretion is of highly variable, unknown concentration. Limited data must never be read as evidence of safety.[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 Greatly potentiate and prolong effects, with serious serotonin-toxicity risk.
SSRIs, Other serotonergic drugs Serotonin-syndrome risk.
Stimulants (amphetamines, cocaine) Additive cardiovascular effects.
Contraindications
Personal or family history of psychosis, schizophrenia or bipolar disorder
Cardiovascular disease, hypertension or arrhythmia
Concurrent MAOI, SSRI/SNRI or other serotonergic medication
Pregnancy or breastfeeding
No interactions or contraindications listed.
Usage & Context
- Research.
- Traditional.
- Recreational.
Sources & Evidence
- Ermakova AO, Dunbar F, Rucker J, et al. (2022). A narrative synthesis of research with 5-MeO-DMT. J Psychopharmacol 36:273-294.
PMID 34666554 · doi:10.1177/02698811211050543
- Sklerov J, Levine B, Moore KA, et al. (2005). A fatal intoxication following the ingestion of 5-methoxy-N,N-dimethyltryptamine in an ayahuasca preparation. J Anal Toxicol 29:838-41.
PMID 16356341 · doi:10.1093/jat/29.8.838
- Glatfelter GC, Clark AA, Cavalco NG, et al. (2024). Serotonin 1A Receptors Modulate Serotonin 2A Receptor-Mediated Behavioral Effects of 5-Methoxy-N,N-dimethyltryptamine Analogs in Mice. ACS Chem Neurosci 15:4458-4477.
PMID 39636099 · doi:10.1021/acschemneuro.4c00513
- Warren AL, Lankri D, Cunningham MJ, et al. (2024). Structural pharmacology and therapeutic potential of 5-methoxytryptamines. Nature 630:237-246.
PMID 38720072 · doi:10.1038/s41586-024-07403-2
- PsychonautWiki: 5-MeO-DMT (dosage & duration) CC BY-SA 4.0
- Wikipedia: 5-MeO-DMT CC BY-SA 4.0
- PubChem (experimental properties)