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
Thumb
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

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
U5-hydroxytryptamine receptor 1A
agonist
Humans
U5-hydroxytryptamine receptor 2A
agonist
Humans
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
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when 1,2-Benzodiazepine is combined with 5-methoxy-N,N-dimethyltryptamine.
AbataceptThe metabolism of 5-methoxy-N,N-dimethyltryptamine can be increased when combined with Abatacept.
AbirateroneThe metabolism of 5-methoxy-N,N-dimethyltryptamine can be decreased when combined with Abiraterone.
AcebutololThe metabolism of 5-methoxy-N,N-dimethyltryptamine can be decreased when combined with Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Aceclofenac is combined with 5-methoxy-N,N-dimethyltryptamine.
AcemetacinThe risk or severity of hypertension can be increased when Acemetacin is combined with 5-methoxy-N,N-dimethyltryptamine.
AcenocoumarolThe risk or severity of adverse effects can be increased when 5-methoxy-N,N-dimethyltryptamine is combined with Acenocoumarol.
AcetaminophenThe metabolism of 5-methoxy-N,N-dimethyltryptamine can be decreased when combined with Acetaminophen.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with 5-methoxy-N,N-dimethyltryptamine.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with 5-methoxy-N,N-dimethyltryptamine.
Interactions
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Food Interactions
Not Available

Categories

Drug Categories
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
  1. 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]
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
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHealthy Subjects (HS)1
1RecruitingTreatmentPharmacokinetics in Healthy Adults1
1, 2RecruitingTreatmentDepression / Major Depressive Disorder (MDD) / Major depressive disorder, recurrent episode1

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
PropertyValueSource
Water Solubility0.723 mg/mLALOGPS
logP2.38ALOGPS
logP2.14ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)17.44ChemAxon
pKa (Strongest Basic)9.58ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area28.26 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity66.91 m3·mol-1ChemAxon
Polarizability25.47 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-014i-0090000000-81cb5c66bea4c4f559a7
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-05fr-5910000000-e732961434e6f6d047c6
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-0ab9-8900000000-4a1b4b925b663d3894ef
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-0a4i-8900000000-1febcb75852e631248d3
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-0a59-7900000000-dcdf4748d932c86ae91e
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-00di-0900000000-60d541c0869cba86353f
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-0a4i-0900000000-2a00c789bf0a52b49304
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-0090000000-81cb5c66bea4c4f559a7
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-05fr-5910000000-7d365fd4fa5aeedebef6
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0ab9-8900000000-4a1b4b925b663d3894ef
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-8900000000-57e4ec6d746c4ef2bd66
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a59-7900000000-995a794ee19726d9dad1
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-00di-0900000000-026ae917940e27f31556
MS/MS Spectrum - , positiveLC-MS/MSsplash10-05ai-2900000000-8e19cf440ade1a459473
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Targets

Drugtargets2
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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
  1. 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
  1. 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
  1. 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