This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Generic Name
- 5-methoxy-N,N-dimethyltryptamine
- DrugBank Accession Number
- DB14010
- Background
5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT) is a tryptamine with psychedelic properties. It is found in a wide variety of plant species, and a single psychoactive toad species, the Colorado River toad. This drug, as well as dimethyltryptamine and bufotenin, have been registered to be used in South America in religious and spiritual rituals.
- Type
- Small Molecule
- Groups
- Experimental, Illicit
- Structure
Structure for 5-methoxy-N,N-dimethyltryptamine (DB14010)
- Weight
- Average: 218.2948
Monoisotopic: 218.141913208 - Chemical Formula
- C13H18N2O
- Synonyms
- 3-(2-dimethylaminoethyl)-5-methoxyindole
- 3-[2-(N,N-Dimethylamino)ethyl]-5-methoxy-indole
- 5-MeO-DMT
- 5-methoxy-N,N-dimethyl-1H-indole-3-ethanamine
- MeODMT
- Methoxybufotenin
- N,N-dimethyl-5-methoxytryptamine
- O-methylbufotenine
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism U5-hydroxytryptamine receptor 1A agonistHumans U5-hydroxytryptamine receptor 2A agonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when 1,2-Benzodiazepine is combined with 5-methoxy-N,N-dimethyltryptamine. Abatacept The metabolism of 5-methoxy-N,N-dimethyltryptamine can be increased when combined with Abatacept. Abiraterone The metabolism of 5-methoxy-N,N-dimethyltryptamine can be decreased when combined with Abiraterone. Acebutolol The metabolism of 5-methoxy-N,N-dimethyltryptamine can be decreased when combined with Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Aceclofenac is combined with 5-methoxy-N,N-dimethyltryptamine. - Food Interactions
- Not Available
Categories
- Drug Categories
- Agents that produce hypertension
- Amines
- Antidepressive Agents
- Biogenic Amines
- Biogenic Monoamines
- Central Nervous System Depressants
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 Substrates
- Heterocyclic Compounds, Fused-Ring
- Indoles
- N,N-Dimethyltryptamine
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin 5-HT1 Receptor Agonists
- Serotonin 5-HT2 Receptor Agonists
- Serotonin Agents
- Serotonin Receptor Agonists
- Tryptamines
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- X0MKX3GWU9
- CAS number
- 1019-45-0
- InChI Key
- 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
- IUPAC Name
- [2-(5-methoxy-1H-indol-3-yl)ethyl]dimethylamine
- SMILES
- COC1=CC=C2NC=C(CCN(C)C)C2=C1
References
- General References
- Shen HW, Jiang XL, Winter JC, Yu AM: Psychedelic 5-methoxy-N,N-dimethyltryptamine: metabolism, pharmacokinetics, drug interactions, and pharmacological actions. Curr Drug Metab. 2010 Oct;11(8):659-66. [Article]
- External Links
- Human Metabolome Database
- HMDB0002004
- KEGG Compound
- C08309
- ChemSpider
- 1766
- BindingDB
- 30707
- ChEBI
- 2086
- ChEMBL
- CHEMBL7257
- ZINC
- ZINC000000057152
- Wikipedia
- 5-MeO-DMT
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 2 Recruiting Treatment Bipolar Disorder, Type II 1 2 Recruiting Treatment Major depressive disorder, recurrent episode 1 2 Recruiting Treatment Postnatal Depression / Postpartum Depression 1 1 Completed Other Pharmacokinetics / Safety / Tolerability 1 1 Completed Treatment Healthy Subjects (HS) 3
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.723 mg/mL ALOGPS logP 2.38 ALOGPS logP 2.14 Chemaxon logS -2.5 ALOGPS pKa (Strongest Acidic) 17.44 Chemaxon pKa (Strongest Basic) 9.58 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 28.26 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 66.91 m3·mol-1 Chemaxon Polarizability 25.47 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 161.9956116 predictedDarkChem Lite v0.1.0 [M-H]- 157.7925116 predictedDarkChem Lite v0.1.0 [M-H]- 161.0335116 predictedDarkChem Lite v0.1.0 [M-H]- 158.3814116 predictedDarkChem Lite v0.1.0 [M-H]- 149.87224 predictedDeepCCS 1.0 (2019) [M+H]+ 164.2849116 predictedDarkChem Lite v0.1.0 [M+H]+ 157.5448547 predictedDarkChem Standard v0.1.0 [M+H]+ 163.3396116 predictedDarkChem Lite v0.1.0 [M+H]+ 158.7511116 predictedDarkChem Lite v0.1.0 [M+H]+ 152.23024 predictedDeepCCS 1.0 (2019) [M+Na]+ 162.4361116 predictedDarkChem Lite v0.1.0 [M+Na]+ 158.4956116 predictedDarkChem Lite v0.1.0 [M+Na]+ 161.7230116 predictedDarkChem Lite v0.1.0 [M+Na]+ 158.7536116 predictedDarkChem Lite v0.1.0 [M+Na]+ 158.48653 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Serotonin receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
- Gene Name
- HTR1A
- Uniprot ID
- P08908
- Uniprot Name
- 5-hydroxytryptamine receptor 1A
- Molecular Weight
- 46106.335 Da
References
- Riga MS, Bortolozzi A, Campa L, Artigas F, Celada P: The serotonergic hallucinogen 5-methoxy-N,N-dimethyltryptamine disrupts cortical activity in a regionally-selective manner via 5-HT(1A) and 5-HT(2A) receptors. Neuropharmacology. 2016 Feb;101:370-8. doi: 10.1016/j.neuropharm.2015.10.016. Epub 2015 Oct 23. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Virus receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
- Gene Name
- HTR2A
- Uniprot ID
- P28223
- Uniprot Name
- 5-hydroxytryptamine receptor 2A
- Molecular Weight
- 52602.58 Da
References
- Riga MS, Bortolozzi A, Campa L, Artigas F, Celada P: The serotonergic hallucinogen 5-methoxy-N,N-dimethyltryptamine disrupts cortical activity in a regionally-selective manner via 5-HT(1A) and 5-HT(2A) receptors. Neuropharmacology. 2016 Feb;101:370-8. doi: 10.1016/j.neuropharm.2015.10.016. Epub 2015 Oct 23. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Shen HW, Jiang XL, Winter JC, Yu AM: Psychedelic 5-methoxy-N,N-dimethyltryptamine: metabolism, pharmacokinetics, drug interactions, and pharmacological actions. Curr Drug Metab. 2010 Oct;11(8):659-66. [Article]
Drug created at April 16, 2018 18:10 / Updated at June 12, 2020 16:53