Dimethyltryptamine

Identification

Name
Dimethyltryptamine
Accession Number
DB01488
Type
Small Molecule
Groups
Experimental, Illicit
Description

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.

Structure
Thumb
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
Categories
UNII
WUB601BHAA
CAS number
61-50-7
Weight
Average: 188.2688
Monoisotopic: 188.131348522
Chemical Formula
C12H16N2
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

Pharmacology

Indication

Some people use this compound as a psychedelic inducing agent.

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 AvailableHuman
U5-hydroxytryptamine receptor 2ANot AvailableHuman
USigma non-opioid intracellular receptor 1Not AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AcetazolamideThe risk or severity of adverse effects can be increased when Dimethyltryptamine is combined with Acetazolamide.
AlfentanilThe risk or severity of serotonin syndrome can be increased when Alfentanil is combined with Dimethyltryptamine.
AlimemazineThe risk or severity of adverse effects can be increased when Dimethyltryptamine is combined with Alimemazine.
AlmotriptanThe risk or severity of serotonin syndrome can be increased when Almotriptan is combined with Dimethyltryptamine.
AlosetronThe risk or severity of adverse effects can be increased when Dimethyltryptamine is combined with Alosetron.
AlprazolamThe risk or severity of adverse effects can be increased when Alprazolam is combined with Dimethyltryptamine.
AmantadineThe risk or severity of serotonin syndrome can be increased when Dimethyltryptamine is combined with Amantadine.
AmikacinThe risk or severity of adverse effects can be increased when Dimethyltryptamine is combined with Amikacin.
AmitriptylineThe risk or severity of serotonin syndrome can be increased when Amitriptyline is combined with Dimethyltryptamine.
AmoxapineThe risk or severity of serotonin syndrome can be increased when Amoxapine is combined with Dimethyltryptamine.
Food Interactions
Not Available

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. [PubMed:8297216]
  2. Callaway JC: A proposed mechanism for the visions of dream sleep. Med Hypotheses. 1988 Jun;26(2):119-24. [PubMed:3412201]
External Links
Human Metabolome Database
HMDB0005973
KEGG Compound
C08302
PubChem Compound
6089
PubChem Substance
46507463
ChemSpider
5864
BindingDB
50026868
ChEBI
28969
ChEMBL
CHEMBL12420
IUPHAR
141
Guide to Pharmacology
GtP Drug Page
Wikipedia
Dimethyltryptamine

Clinical Trials

Clinical Trials
Not Available

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

Taxonomy

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
Tryptamine / 3-alkylindole / Indole / Aralkylamine / Substituted pyrrole / Benzenoid / Pyrrole / Heteroaromatic compound / Tertiary aliphatic amine / Tertiary amine
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tryptamine alkaloid, tryptamines (CHEBI:28969) / Indole alkaloids (C08302)

Targets

Kind
Protein
Organism
Human
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. [PubMed:10715164]
  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. [PubMed:17239595]
  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. [PubMed:270770]
  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. [PubMed:278843]
Kind
Protein
Organism
Human
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. [PubMed:2540505]
  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. [PubMed:19278957]
Kind
Protein
Organism
Human
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. [PubMed:19278957]

Drug created on July 31, 2007 07:09 / Updated on October 01, 2018 13:04