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Dimethyltryptamine

PubChem CID: 6089

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Compound Synonyms N,N-DIMETHYLTRYPTAMINE, DIMETHYLTRYPTAMINE, 61-50-7, 2-(3-Indolyl)ethyldimethylamine, 3-(2-Dimethylaminoethyl)indole, 1H-Indole-3-ethanamine, N,N-dimethyl-, 2-(1H-Indol-3-yl)-N,N-dimethylethanamine, N,N-Dimethyl-1H-indole-3-ethylamine, DMT (psychogenic), N,N-dimethyl-1H-Indole-3-ethanamine, DEA No. 7435, UNII-WUB601BHAA, 3-[2-(dimethylamino)ethyl]indole, WUB601BHAA, EINECS 200-508-4, NSC 63795, BRN 0138259, CHEBI:28969, HSDB 8017, NSC-63795, N-DIMETHYLTRYPTAMINE, Indole, 3-(2-(dimethylamino)ethyl)-, CHEMBL12420, DTXSID60110053, (2-Indol-3-ylethyl)dimethylamine, Indole, 3-[2-(dimethylamino)ethyl]-, 3-(2-(DIMETHYLAMINO)ETHYL)INDOLE, DIMETHYLTRYPTAMINE (MART.), DIMETHYLTRYPTAMINE [MART.], (psychogenic), N,N-Dimethyltryptamine (1mg/ml in Methanol), N,N Dimethyltryptamine, N,N-Dimethyltryptamine (1mg/ml in Acetonitrile), 2-(1H-INDOL-3-YL)-N,N-DIMETHYL-ETHANAMINE, NN-Dimethyltryptamine, Dimethyltryptamine(DMT), dimethyltryptamine [INN], (N,N)-Dimethyltryptamine, GTPL141, 3-(dimethylaminoethyl)-indole, SCHEMBL335710, [2-(1H-INDOL-3-YL)-ETHYL]-DIMETHYL-AMINE, DTXCID4065313, METHYL-(2-(1H-INDOL-3-YL)-ETHYL)-METHYLAMINE, N,N-Dimethyltryptamine, free base, DIMETHYLTRYPTAMINE [WHO-DD], N,N-DIMETHYLTRYPTAMINE [MI], NSC63795, WLN: T56 BMJ D2N1&1, 3-(2-(dimethylamino)ethyl)-Indole, BDBM50026868, STK370594, 3-[2- (dimethylamino)ethyl]-Indole, AKOS005446117, 3-(2-Dimethylaminoethyl) indole, DMT, DB01488, MB00483, [2-(1H-indol-3-yl)ethyl]dimethylamine, 3-(2-DIMETHYLAMINOETHYL) INDOLE, 2-(1H-indol-3-yl)-ethyl-dimethyl-amine, AS-47089, N,N-Dimethyltryptamine, >=97% (HPLC), 2-(1H-indol-3-yl)-N,N-dimethylethylamine, DB-308391, N,N-Dimethyltryptamine, 1mg/ml in Methanol, 1H-INDOLE-3-ETHANAMINE,N,N-DIMETHYL, NS00005525, N,N-dimethyl-1H-Indole-3-ethanamine (9CI), 2-(1H-Indol-3-yl)-N,N-dimethylethanamine #, C08302, D-5500, L001288, Q407217, 2-(1H-indol-3-yl)-N,N-dimethylethanamine (ACD/Name 4.0), N-(2-(1H-indol-3-yl)ethyl)-N,N-dimethylamine (ACD/Name 4.0), 200-508-4, InChI=1/C12H16N2/c1-14(2)8-7-10-9-13-12-6-4-3-5-11(10)12/h3-6,9,13H,7-8H2,1-2H
Ghose Rule True
Classyfire Kingdom Organic compounds
Topological Polar Surface Area 19.0
Hydrogen Bond Donor Count 1.0
Pfizer 3 75 Rule False
Scaffold Graph Level C1CCC2CCCC2C1
Np Classifier Class Simple indole alkaloids
Deep Smiles CNCCcc[nH]cc5cccc6)))))))))))C
Heavy Atom Count 14.0
Classyfire Class Indoles and derivatives
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., 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]
Scaffold Graph Node Level C1CCC2NCCC2C1
Classyfire Subclass Tryptamines and derivatives
Isotope Atom Count 0.0
Molecular Complexity 179.0
Database Name cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem
Defined Atom Stereocenter Count 0.0
Uniprot Id Q9ES14, P30994, P28565, P14842, P19327, P28223, P41595, P28335, P08908, Q60492, n.a., Q9R0C9
Iupac Name 2-(1H-indol-3-yl)-N,N-dimethylethanamine
Prediction Hob 1.0
Class Indoles and derivatives
Veber Rule True
Classyfire Superclass Organoheterocyclic compounds
Target Id NPT290, NPT291, NPT292, NPT92
Xlogp 2.5
Superclass Organoheterocyclic compounds
Subclass Tryptamines and derivatives
Gsk 4 400 Rule True
Molecular Formula C12H16N2
Scaffold Graph Node Bond Level c1ccc2[nH]ccc2c1
Prediction Swissadme 0.0
Inchi Key DMULVCHRPCFFGV-UHFFFAOYSA-N
Silicos It Class Moderately soluble
Fcsp3 0.3333333333333333
Logs -1.616
Rotatable Bond Count 3.0
State Solid
Logd 1.997
Synonyms (2-Indol-3-ylethyl)dimethylamine, (psychogenic), 2-(1H-Indol-3-yl)-N,N-dimethylethanamine, 2-(1H-indol-3-yl)-N,N-dimethylethanamine (ACD/Name 4.0), 2-(3-Indolyl)ethyldimethylamine, 3-(2-(dimethylamino)ethyl)-Indole, 3-(2-Dimethylaminoethyl)indole, 3-[2- (dimethylamino)ethyl]-Indole, 3-[2-(dimethylamino)Ethyl]indole, Dimethyltryptamine(DMT), DMT, Indolalkylamine der, N-(2-(1H-indol-3-yl)ethyl)-N,N-dimethylamine (ACD/Name 4.0), N,N-dimethyl-1H-Indole-3-ethanamine, N,N-dimethyl-1H-Indole-3-ethanamine (9CI), N,N-Dimethyl-1H-indole-3-ethylamine, N,n-dimethyltryptamine, 3-[2-(Dimethylamino)ethyl]indole, N,N Dimethyltryptamine, (2-indol-3-Ylethyl)dimethylamine, (Psychogenic), 2-(1H-indol-3-yl)-N,N-Dimethylethanamine, 2-(1H-indol-3-yl)-N,N-Dimethylethanamine (acd/name 4.0), 3-(2-(dimethylamino)Ethyl)-indole, 3-[2- (dimethylamino)Ethyl]-indole, N,N-Dimethyl-1H-indole-3-ethanamine, N,N-Dimethyl-1H-indole-3-ethanamine (9ci), N,N-Dimethyltryptamine, N-(2-(1H-indol-3-yl)Ethyl)-N,N-dimethylamine (acd/name 4.0), Dimethyltryptamine, dimethyltryptamine, n, n-dimethyltryptamine, n,n-dimethyl-tryptamine, n,n-dimethyltryptamine
Substituent Name Tryptamine, Indole, Aralkylamine, Benzenoid, Substituted pyrrole, Heteroaromatic compound, Pyrrole, Tertiary aliphatic amine, Tertiary amine, Azacycle, Hydrocarbon derivative, Organonitrogen compound, Amine, Aromatic heteropolycyclic compound
Esol Class Soluble
Functional Groups CN(C)C, c[nH]c
Compound Name Dimethyltryptamine
Kingdom Organic compounds
Prediction Hob Swissadme 0.0
Exact Mass 188.131
Formal Charge 0.0
Monoisotopic Mass 188.131
Hydrogen Bond Acceptor Count 1.0
Molecular Weight 188.27
Gi Absorption True
Covalent Unit Count 1.0
Total Atom Stereocenter Count 0.0
Total Bond Stereocenter Count 0.0
Molecular Framework Aromatic heteropolycyclic compounds
Lipinski Rule Of 5 True
Esol -2.3434130857142854
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
Smiles CN(C)CCC1=CNC2=CC=CC=C21
Nring 2.0
Np Classifier Biosynthetic Pathway Alkaloids
Defined Bond Stereocenter Count 0.0
Egan Rule True
Taxonomy Direct Parent Tryptamines and derivatives
Np Classifier Superclass Tryptophan alkaloids

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