Dimethyltryptamine

Identification

Generic Name
Dimethyltryptamine
DrugBank Accession Number
DB01488
Background

An N-methylated indoleamine derivative, a serotonergic hallucinogen found in several plants, especially Prestonia amazonica (Apocynaceae) and in mammalian brain, blood, and urine. It apparently acts as an agonist at some types of serotonin receptors and an antagonist at others.

Type
Small Molecule
Groups
Experimental, Illicit
Structure
Thumb
Weight
Average: 188.2688
Monoisotopic: 188.131348522
Chemical Formula
C12H16N2
Synonyms
  • 2-(3-indolyl)ethyldimethylamine
  • 3-(2-dimethylaminoethyl)indole
  • 3-[2-(dimethylamino)ethyl]indole
  • DMT
  • N,N-dimethyl-1H-indole-3-ethylamine
  • N,N-dimethyltryptamine
External IDs
  • DEA NO. 7435
  • NSC-63795

Pharmacology

Indication

Some people use this compound as a psychedelic inducing agent.

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action

DMT acts as a non-selective agonist at most or all of the serotonin receptors.

TargetActionsOrganism
A5-hydroxytryptamine receptor 6Not AvailableHumans
U5-hydroxytryptamine receptor 2ANot AvailableHumans
USigma non-opioid intracellular receptor 1Not AvailableHumans
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
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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 Dimethyltryptamine is combined with 1,2-Benzodiazepine.
AcenocoumarolThe risk or severity of adverse effects can be increased when Dimethyltryptamine is combined with Acenocoumarol.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Dimethyltryptamine.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Dimethyltryptamine.
AclidiniumDimethyltryptamine may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Dimethyltryptamine is combined with Agomelatine.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Dimethyltryptamine.
AlimemazineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Dimethyltryptamine.
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Dimethyltryptamine.
AlosetronThe risk or severity of adverse effects can be increased when Alosetron is combined with Dimethyltryptamine.
Interactions
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as tryptamines and derivatives. These are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Tryptamines and derivatives
Direct Parent
Tryptamines and derivatives
Alternative Parents
3-alkylindoles / Aralkylamines / Substituted pyrroles / Benzenoids / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
3-alkylindole / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Heteroaromatic compound / Hydrocarbon derivative / Indole / Organic nitrogen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tryptamine alkaloid, tryptamines (CHEBI:28969) / Indole alkaloids (C08302)
Affected organisms
Not Available

Chemical Identifiers

UNII
WUB601BHAA
CAS number
61-50-7
InChI Key
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
IUPAC Name
[2-(1H-indol-3-yl)ethyl]dimethylamine
SMILES
CN(C)CCC1=CNC2=CC=CC=C12

References

General References
  1. Strassman RJ, Qualls CR: Dose-response study of N,N-dimethyltryptamine in humans. I. Neuroendocrine, autonomic, and cardiovascular effects. Arch Gen Psychiatry. 1994 Feb;51(2):85-97. [Article]
  2. Callaway JC: A proposed mechanism for the visions of dream sleep. Med Hypotheses. 1988 Jun;26(2):119-24. [Article]
Human Metabolome Database
HMDB0005973
KEGG Compound
C08302
PubChem Compound
6089
PubChem Substance
46507463
ChemSpider
5864
BindingDB
50026868
ChEBI
28969
ChEMBL
CHEMBL12420
ZINC
ZINC000000897457
Guide to Pharmacology
GtP Drug Page
Wikipedia
Dimethyltryptamine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHealthy Volunteers1
1Not Yet RecruitingBasic ScienceHealthy Volunteers1
1RecruitingOtherDepression / Major Depressive Disorder (MDD)1
1, 2RecruitingTreatmentDepression / Major Depressive Disorder (MDD) / Major depressive disorder, recurrent episode / Treatment Resistant Depression (TRD)1
1, 2RecruitingTreatmentMajor Depressive Disorder (MDD)1
0RecruitingBasic ScienceCognitive Function 1, Social / Emotions / Empathy / Mood1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)46 °CPhysProp
pKa8.68MERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility1.69 mg/mLALOGPS
logP2.41ALOGPS
logP2.3ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)17.16ChemAxon
pKa (Strongest Basic)9.55ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area19.03 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity60.44 m3·mol-1ChemAxon
Polarizability22.32 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9797
Caco-2 permeable+0.6601
P-glycoprotein substrateSubstrate0.634
P-glycoprotein inhibitor INon-inhibitor0.9304
P-glycoprotein inhibitor IINon-inhibitor0.6713
Renal organic cation transporterInhibitor0.7268
CYP450 2C9 substrateNon-substrate0.8154
CYP450 2D6 substrateSubstrate0.5974
CYP450 3A4 substrateSubstrate0.5824
CYP450 1A2 substrateNon-inhibitor0.8597
CYP450 2C9 inhibitorNon-inhibitor0.9436
CYP450 2D6 inhibitorNon-inhibitor0.8744
CYP450 2C19 inhibitorNon-inhibitor0.917
CYP450 3A4 inhibitorNon-inhibitor0.843
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8954
Ames testAMES toxic0.52
CarcinogenicityNon-carcinogens0.9588
BiodegradationNot ready biodegradable0.9795
Rat acute toxicity2.6187 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8972
hERG inhibition (predictor II)Non-inhibitor0.7733
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (7.49 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0a4i-9100000000-27639de9acc9e554bfc8
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

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
General Function
Serotonin receptor activity
Specific Function
This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor ...
Gene Name
HTR6
Uniprot ID
P50406
Uniprot Name
5-hydroxytryptamine receptor 6
Molecular Weight
46953.625 Da
References
  1. Glennon RA, Lee M, Rangisetty JB, Dukat M, Roth BL, Savage JE, McBride A, Rauser L, Hufeisen S, Lee DK: 2-Substituted tryptamines: agents with selectivity for 5-HT(6) serotonin receptors. J Med Chem. 2000 Mar 9;43(5):1011-8. [Article]
  2. Nyandege A, Kolanos R, Roth BL, Glennon RA: Further studies on the binding of N1-substituted tryptamines at h5-HT6 receptors. Bioorg Med Chem Lett. 2007 Mar 15;17(6):1691-4. Epub 2007 Jan 4. [Article]
  3. Glennon RA, Gessner PK: The electronic and serotonin receptor binding affinity properties of N,N-dimethyltryptamine analogs. Res Commun Chem Pathol Pharmacol. 1977 Nov;18(3):453-65. [Article]
  4. Glennon RA, Liebowitz SM, Mack EC: Serotonin receptor binding affinities of several hallucinogenic phenylalkylamine and N,N-dimethyltryptamine analogues. J Med Chem. 1978 Aug;21(8):822-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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. Pierce PA, Peroutka SJ: Hallucinogenic drug interactions with neurotransmitter receptor binding sites in human cortex. Psychopharmacology (Berl). 1989;97(1):118-22. [Article]
  2. Su TP, Hayashi T, Vaupel DB: When the endogenous hallucinogenic trace amine N,N-dimethyltryptamine meets the sigma-1 receptor. Sci Signal. 2009 Mar 10;2(61):pe12. doi: 10.1126/scisignal.261pe12. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Opioid receptor activity
Specific Function
Functions in lipid transport from the endoplasmic reticulum and is involved in a wide array of cellular functions probably through regulation of the biogenesis of lipid microdomains at the plasma m...
Gene Name
SIGMAR1
Uniprot ID
Q99720
Uniprot Name
Sigma non-opioid intracellular receptor 1
Molecular Weight
25127.52 Da
References
  1. Su TP, Hayashi T, Vaupel DB: When the endogenous hallucinogenic trace amine N,N-dimethyltryptamine meets the sigma-1 receptor. Sci Signal. 2009 Mar 10;2(61):pe12. doi: 10.1126/scisignal.261pe12. [Article]

Drug created on July 31, 2007 13:09 / Updated on June 12, 2020 16:51