You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2007-04-12 19:07:12 UTC
Update Date2016-05-13 22:43:50 UTC
HMDB IDHMDB05973
Secondary Accession NumbersNone
Metabolite Identification
Common NameDimethyltryptamine
DescriptionDimethyltryptamine is 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. DMT is a derivative of tryptamine with two additional methyl groups at the amine nitrogen atom. DMT is often synthesized by the Speeter-Anthony synthesis from indole using oxalyl chloride, dimethylamine, and lithium aluminium hydride as reagents. DMT is usually used in its base form, but it is more stable as a salt, e.g. as a fumarate. In contrast to DMT's base, its salts are water-soluble. DMT in solution degrades relatively fast and should be stored protected from air and light in a freezer. Highly pure DMT crystals, when evaporated out of a solvent and depositing upon glass, often produce small but highly defined white crystalline needles which when viewed under intense light will sparkle, and appear colorless under high magnification. In labs, it has been known to be explosive under a certain degree of heat. DMT is a powerful psychoactive substance. If DMT is smoked, injected, or orally ingested with an MAOI, it can produce powerful entheogenic experiences including intense visual hallucinations, euphoria, even true hallucinations (perceived extensions of reality). A trip sitter is recommended to assist the drug user in staying physically and mentally healthy, and, in the case of smoked DMT, to catch the pipe if the user loses awareness of it. DMT is classified in the United States as a Schedule I drug. There are no drug tests that would show DMT usage. None of the basic NIDA 5 drug tests or any extended drug test will show a result for DMT. Dimethyltryptamine (DMT), also known as N,N-dimethyltryptamine, is a psychedelic tryptamine. It is not to be confused with 5-MeO-DMT and is similar in chemical structure to the neurotransmitter serotonin. DMT is created in small amounts by the human body during normal metabolism by the enzyme tryptamine-N-methyltransferase. Pure DMT at room temperature is a clear or white crystalline solid. DMT was first chemically synthesized in 1931. It also occurs naturally in many species of plants. DMT-containing plants are used in several South American shamanic practices. It is one of the main active constituents of snuffs like yopo and of the drink ayahuasca. Oral ingestion: DMT, which is broken down by the digestive enzyme monoamine oxidase, is practically inactive if taken orally, unless combined with a monoamine oxidase inhibitor (MAOI). The traditional South American ayahuasca, or yage, is a tea mixture containing DMT and a MAOI. There are a number of admixtures to this brew, but most commonly it is simply the leaves of Psychotria viridis (containing DMT), and the vine Banisteriopsis caapi (the source of MAOI). Other DMT containing plants, including Diplopterys cabrerana, are sometimes used in ayahuasca in different areas of South America. Two common sources in the western US are Reed canary grass (Phalaris arundinacea) and Harding grass (Phalaris aquatica). These invasive grasses contain low levels of DMT and other alkaloids. Taken orally with an appropriate MAOI, DMT produces a long lasting (over 3 hour), slow, but deep spiritual experience. MAOIs should be used with extreme caution as they can have lethal complications with some prescription drugs, such as SSRI antidepressants, and some over-the-counter drugs. Smoked: If DMT is smoked, the maximal effects last for a short period of time (5-30 minutes dose dependent). The onset after inhalation is very fast (less than 45 seconds) and maximal effects are reached within about a minute. The Business Man's lunch trip is a common name due to the relatively short duration of vaporized, insufflated, or injected DMT.
Structure
Thumb
Synonyms
ValueSource
2-(3-Indolyl)ethyldimethylamineChEBI
3-(2-Dimethylaminoethyl)indoleChEBI
3-[2-(dimethylamino)Ethyl]indoleChEBI
DMTChEBI
N,N-Dimethyl-1H-indole-3-ethylamineChEBI
(2-indol-3-Ylethyl)dimethylamineHMDB
(Psychogenic)HMDB
2-(1H-indol-3-yl)-N,N-DimethylethanamineHMDB
2-(1H-indol-3-yl)-N,N-Dimethylethanamine (acd/name 4.0)HMDB
3-(2-(dimethylamino)Ethyl)-indoleHMDB
3-[2- (dimethylamino)Ethyl]-indoleHMDB
Dimethyltryptamine(DMT)HMDB
Indolalkylamine derHMDB
N,N-Dimethyl-1H-indole-3-ethanamineHMDB
N,N-Dimethyl-1H-indole-3-ethanamine (9ci)HMDB
N,N-DimethyltryptamineHMDB
N-(2-(1H-indol-3-yl)Ethyl)-N,N-dimethylamine (acd/name 4.0)HMDB
Chemical FormulaC12H16N2
Average Molecular Weight188.2688
Monoisotopic Molecular Weight188.131348522
IUPAC Name[2-(1H-indol-3-yl)ethyl]dimethylamine
Traditional Name(psychogenic)
CAS Registry Number61-50-7
SMILES
CN(C)CCC1=CNC2=CC=CC=C12
InChI Identifier
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
InChI KeyInChIKey=DMULVCHRPCFFGV-UHFFFAOYSA-N
Chemical 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
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point46 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
UrineDetected and Quantified0.015 +/- 0.0030 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.001 (0.000056-0.000097) umol/mmol creatinineAdult (>18 years old)BothSurgical patients details
UrineDetected and Quantified0.00069 (0.00014-0.00018) umol/mmol creatinineAdult (>18 years old)BothInternal medical patients details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023795
KNApSAcK IDNot Available
Chemspider ID5864
KEGG Compound IDC08302
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB05973
Metagene LinkHMDB05973
METLIN IDNot Available
PubChem Compound6089
PDB IDNot Available
ChEBI ID28969
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available