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Showing Compound Dimethyltryptamine (FDB023795)

Record Information
Version1.0
Creation date2011-09-21 00:34:50 UTC
Update date2015-07-21 06:57:52 UTC
Primary IDFDB023795
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDimethyltryptamine
DescriptionAn 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. In December of 2004, the Supreme Court lifted a stay thereby allowing the Brazil-based Uniaeo do Vegetal (UDV) church to use a decoction containing DMT in their Christmas services that year. This decoction is a tea made from boiled leaves and vines, known as hoasca within the UDV, and ayahuasca in different cultures. In Gonzales v. O Centro EspArita Beneficente Uniaeo do Vegetal, the Supreme Court heard arguments on November 1, 2005 and unanimously ruled in February 2006 that the U.S. federal government must allow the UDV to import and consume the tea for religious ceremonies under the 1993 Religious Freedom Restoration Act. 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. [HMDB]
CAS Number61-50-7
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility1.69 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity60.44 m³·mol⁻¹ChemAxon
Polarizability22.32 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC12H16N2
IUPAC name[2-(1H-indol-3-yl)ethyl]dimethylamine
InChI IdentifierInChI=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 KeyDMULVCHRPCFFGV-UHFFFAOYSA-N
Isomeric SMILESCN(C)CCC1=CNC2=CC=CC=C12
Average Molecular Weight188.2688
Monoisotopic Molecular Weight188.131348522
Classification
Description Belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted 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
  • 3-alkylindole
  • Indole
  • Aralkylamine
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSDimethyltryptamine, non-derivatized, GC-MS Spectrumsplash10-0a4i-9100000000-27639de9acc9e554bfc8Spectrum
GC-MSDimethyltryptamine, non-derivatized, GC-MS Spectrumsplash10-0a4i-9100000000-27639de9acc9e554bfc8Spectrum
Predicted GC-MSDimethyltryptamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-9200000000-042153089cdf3d352d46Spectrum
Predicted GC-MSDimethyltryptamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSDimethyltryptamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-c4e95be299db18f4261c2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000f-0900000000-c4b763b76c22294771622016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-2900000000-6a66b4f77d8b06ed76d02016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-d1632b5208bba1e684582016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1900000000-e994ffa20ea0cbbdfefb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-5900000000-3006ea79be7c87724d7e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-24d2daab50e20cd397c32021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-0f41a3ef9622491457fc2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-0900000000-89da4200c233f5263ed32021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-6900000000-ea7c1d457228d6c0b37a2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9200000000-6dda2cdd6c28ec834cd72021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9300000000-bc6b375679f045ccc9f62021-09-25View Spectrum
NMRNot Available
ChemSpider ID5864
ChEMBL IDCHEMBL12420
KEGG Compound IDC08302
Pubchem Compound ID6089
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB01488
HMDB IDHMDB05973
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference