N,N-Dimethyltryptamine

N,N-Dimethyltryptamine
Clinical data
Routes of; administration	Oral (with an MAOI), vaporized, insufflated, rectal, IM, IV
ATC code	None;
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class F2 (Prohibited psychotropics); CA: Schedule III; DE: Anlage I (Authorized scientific use only); UK: Class A; US: Schedule I; UN: Psychotropic Schedule I;
Pharmacokinetic data
Elimination half-life	9-12 minutes
Identifiers
	IUPAC name 2-(1H-Indol-3-yl)-N,N-dimethylethanamine;
CAS Number	61-50-7 ;
PubChem CID	6089;
IUPHAR/BPS	141;
DrugBank	DB01488 ;
ChemSpider	5864 ;
UNII	WUB601BHAA;
KEGG	C08302 ;
ChEBI	CHEBI:28969 ;
ChEMBL	ChEMBL12420 ;
CompTox Dashboard (EPA)	DTXSID60110053 ;
ECHA InfoCard	100.000.463
Chemical and physical data
Formula	C12H16N2
Molar mass	188.274 g·mol−1
3D model (JSmol)	Interactive image;
Density	1.099 g/cm3
Melting point	40 °C (104 °F)
Boiling point	160 °C (320 °F) at 0.6 Torr (80 Pa); also reported as; 80–135 °C (176–275 °F) at 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 ; Key:DMULVCHRPCFFGV-UHFFFAOYSA-N ;
	(verify)

N,N-Dimethyltryptamine (DMT or N,N-DMT) is a substituted tryptamine that occurs in many plants and animals, including humans, and which is both a derivative and a structural analog of tryptamine. DMT is used as a psychedelic drug and prepared by various cultures for ritual purposes as an entheogen.

DMT has a rapid onset, intense effects, and a relatively short duration of action. For those reasons, DMT was known as the "businessman's trip" during the 1960s in the United States, as a user could access the full depth of a psychedelic experience in considerably less time than with other substances such as LSD or psilocybin mushrooms. DMT can be inhaled, ingested, or injected and its effects depend on the dose, as well as the mode of administration. When inhaled or injected, the effects last a short period of time: about five to 15 minutes. Effects can last three hours or more when orally ingested along with a monoamine oxidase inhibitor (MAOI), such as the ayahuasca brew of many native Amazonian tribes. DMT can produce vivid "projections" of mystical experiences involving euphoria and dynamic pseudohallucinations of geometric forms.

DMT is a functional analog and structural analog of other psychedelic tryptamines such as O-acetylpsilocin (4-AcO-DMT), psilocybin (4-PO-DMT), psilocin (4-HO-DMT), O-methylbufotenin (5-MeO-DMT), and bufotenin (5-HO-DMT). Parts of the structure of DMT occur within some important biomolecules like serotonin and melatonin, making them structural analogs of DMT.

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