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Human Metabolome Database Version 3.5

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Showing metabocard for Dimethyltryptamine (HMDB05973)

Record Information
Version 3.5
Creation Date 2007-04-12 13:07:12 -0600
Update Date 2013-02-08 17:14:26 -0700
HMDB ID HMDB05973
Secondary Accession Numbers None
Metabolite Identification
Common Name Dimethyltryptamine
Description Dimethyltryptamine 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
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Display: 2D Structure | 3D Structure
Synonyms
  1. (2-Indol-3-ylethyl)dimethylamine
  2. (psychogenic)
  3. 2-(1H-Indol-3-yl)-N,N-dimethylethanamine
  4. 2-(1H-Indol-3-yl)-N,N-dimethylethanamine (ACD/Name 4.0)
  5. 2-(3-Indolyl)ethyldimethylamine
  6. 3-(2-(Dimethylamino)ethyl)-Indole
  7. 3-(2-Dimethylaminoethyl)indole
  8. 3-[2- (Dimethylamino)ethyl]-Indole
  9. Dimethyltryptamine(DMT)
  10. Indolalkylamine der
  11. N,N-Dimethyl-1H-Indole-3-ethanamine
  12. N,N-Dimethyl-1H-Indole-3-ethanamine (9CI)
  13. N,N-Dimethyl-1H-indole-3-ethylamine
  14. N,N-Dimethyltryptamine
  15. N-(2-(1H-Indol-3-yl)ethyl)-N,N-dimethylamine (ACD/Name 4.0)
Chemical Formula C12H16N2
Average Molecular Weight 188.2688
Monoisotopic Molecular Weight 188.131348522
IUPAC Name [2-(1H-indol-3-yl)ethyl]dimethylamine
Traditional IUPAC Name dimethyltryptamine
CAS Registry Number 61-50-7
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 Key DMULVCHRPCFFGV-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Indoles
Sub Class Tryptamines and Derivatives
Other Descriptors
  • Indole alkaloids(KEGG)
  • Indoles
  • tryptamine alkaloid(ChEBI)
  • tryptamines(ChEBI)
Substituents
  • Pyrrole
  • Tertiary Aliphatic Amine (Trialkylamine)
Direct Parent Tryptamines and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 46 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 1.69 g/L ALOGPS
LogP 2.41 ALOGPS
LogP 2.3 ChemAxon
LogS -2.05 ALOGPS
pKa (strongest acidic) 17.16 ChemAxon
pKa (strongest basic) 9.55 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 19.03 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 60.44 ChemAxon
Polarizability 22.32 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Expected and not Quantified
Not Applicable Not Available Not Available Normal Inferred from detection in urine
Urine Detected and Quantified
Article_icon
0.015 +/- 0.0030 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and Quantified
Article_icon
0.001 (0.000056-0.000097) umol/mmol creatinine Adult (>18 years old) Both Surgical patients Not Available
Urine Detected and Quantified
Article_icon
0.00069 (0.00014-0.00018) umol/mmol creatinine Adult (>18 years old) Both Internal medical patients Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023795
KNApSAcK ID Not Available
Chemspider ID 5864 Link_out
KEGG Compound ID C08302 Link_out
BioCyc ID BUFOTENINE Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB05973 Link_out
Metagene Link HMDB05973 Link_out
METLIN ID Not Available
PubChem Compound 6089 Link_out
PDB ID Not Available
ChEBI ID 28969 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available