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Identification
NameDimethyltryptamine
Accession NumberDB01488
TypeSmall Molecule
GroupsExperimental, 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. [PubChem]

Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIWUB601BHAA
CAS number61-50-7
WeightAverage: 188.2688
Monoisotopic: 188.131348522
Chemical FormulaC12H16N2
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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 subsituted at the 3-position by an ethanamine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassTryptamines and derivatives
Direct ParentTryptamines and derivatives
Alternative Parents
Substituents
  • Tryptamine
  • Indole
  • Aralkylamine
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationSome people use this compound as a psychedelic inducing agent.
PharmacodynamicsNot Available
Mechanism of actionDMT acts as a non-selective agonist at most or all of the serotonin receptors.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point46 °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 RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (7.49 KB)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
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
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

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 is mediated by G proteins that stimulate adenylate cyclase. It has a high affinity for tricyclic psychotropic drugs (By similarity). Controls pyramidal neurons migration during corticogenesis, through...
Gene Name:
HTR6
Uniprot ID:
P50406
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-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates...
Gene Name:
HTR2A
Uniprot ID:
P28223
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 membrane. Involved in the regulation of different receptors it plays a role in BDNF signaling and EGF signaling. Also regulates ion channels like the potassium channel and could modulate neurotransmitt...
Gene Name:
SIGMAR1
Uniprot ID:
Q99720
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 ]
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Drug created on July 31, 2007 07:09 / Updated on August 17, 2016 12:23