N,N-dimethyltryptamine

N,N-Dimethyltryptamine
Clinical data


Routes of administration	Oral (with an MAOI), insufflated, rectal, vaporized, IM, IV
ATC code	none
Legal status
Legal status	AU: S9 (Prohibited) CA: Schedule III DE: Anlage I (Controlled) UK: Controlled Drug Lic US: Schedule I
Identifiers
IUPAC name 2-(1H-Indol-3-yl)-N,N-dimethylethanamine
CAS Number	61-50-7^Y
PubChem CID	6089
IUPHAR/BPS	141
DrugBank	DB01488^Y
ChemSpider	5864^Y
UNII	WUB601BHAA
KEGG	C08302^Y
ChEBI	CHEBI:28969^Y
ChEMBL	CHEMBL12420^Y
ECHA InfoCard	100.000.463
Chemical and physical data
Formula	C₁₂H₁₆N₂
Molar mass	188.269 g/mol
3D model (Jmol)	Interactive image
Density	1.099 g/cm³
Melting point	40 °C (104 °F)
Boiling point	160 °C (320 °F) @ 0.6 Torr (80 Pa) also reported as 80–135 °C (176–275 °F) @ 0.03 Torr (4.0 Pa)
SMILES CN(CCC1=CNC2=C1C=CC=C2)C
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^Y Key:DMULVCHRPCFFGV-UHFFFAOYSA-N^Y

N,N-Dimethyltryptamine (DMT or N,N-DMT) is a powerful psychedelic compound of the tryptamine family. It is a structural analog of serotonin and melatonin and a functional analog of other psychedelic tryptamines such as 4-AcO-DMT, 5-MeO-DMT, 5-HO-DMT, psilocybin (4-PO-DMT), and psilocin (4-HO-DMT).

Historically, it has been consumed by indigenous Amazonian Indian cultures in the form of ayahuasca for divinatory and healing purposes. It was first synthesised in 1931, and in 1946, microbiologist Oswaldo Gonçalves de Lima discovered its natural presence in plants. In the 1960s, it was detected in mammalian organisms as well.

DMT is known for its relatively short duration of action, intense effects and rapid onset. For that reason, DMT was known as a "businessman's trip" during the 1960s in the United States.

DMT can be inhaled, injected, or orally ingested, and its effects depend on the dose, both of DMT and of any MAOI taken with it. The effects last a short period of time, 5 to 15 min. Longer effects can be achieved by oral ingestion: over 3 hours. DMT can produce psychedelic experiences involving euphoria and hallucinations. In most countries, DMT is illegal.

The dependence potential of DMT and the risk of sustained psychological disturbance are minimal when used for religious ceremonies. DMT, like most psychedelics, is considered to be neither addictive, nor toxic, although there is a rare chance some might develop a psychological dependence.

According to a dose-response study, "dimethyltryptamine dose slightly elevated blood pressure, heart rate, pupil diameter, and rectal temperature, in addition to elevating blood concentrations of beta-endorphin, corticotropin, cortisol, and prolactin. Growth hormone blood levels rose equally in response to all doses of DMT, and melatonin levels were unaffected."

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