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.^[4] DMT is used as a psychedelic drug and prepared by various cultures for ritual purposes as an entheogen.^[5]

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.^[6] 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.^[7] DMT can produce vivid "projections" of mystical experiences involving euphoria and dynamic pseudohallucinations of geometric forms.^[8]

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.

^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
^ Häfelinger G, Nimtz M, Horstmann V, Benz T (1999). "Untersuchungen zur Trifluoracetylierung der Methylderivate von Tryptamin und Serotonin mit verschiedenen Derivatisierungsreagentien: Synthesen, Spektroskopie sowie analytische Trennungen mittels Kapillar-GC" [Trifluoracetylation of methylated derivatives of tryptamine and serotonin by different reagents: synthesis, spectroscopic characterizations, and separations by capillary gas chromatography]. Zeitschrift für Naturforschung B. 54 (3): 397–414. doi:10.1515/znb-1999-0319. S2CID 101000504.
^ Corothie E, Nakano T (May 1969). "Constituents of the bark of Virola sebifera". Planta Medica. 17 (2): 184–188. doi:10.1055/s-0028-1099844. PMID 5792479. S2CID 43312376.
^ Carbonaro TM, Gatch MB (September 2016). "Neuropharmacology of N,N-dimethyltryptamine". Brain Research Bulletin. 126 (Pt 1): 74–88. doi:10.1016/j.brainresbull.2016.04.016. PMC 5048497. PMID 27126737.
^ McKenna DJ, Towers GH, Abbott F (April 1984). "Monoamine oxidase inhibitors in South American hallucinogenic plants: tryptamine and beta-carboline constituents of ayahuasca". Journal of Ethnopharmacology. 10 (2): 195–223. doi:10.1016/0378-8741(84)90003-5. PMID 6587171.
^ Haroz R, Greenberg MI (November 2005). "Emerging drugs of abuse". The Medical Clinics of North America. 89 (6): 1259–1276. doi:10.1016/j.mcna.2005.06.008. OCLC 610327022. PMID 16227062.
^ Pickover C (2005). Sex, Drugs, Einstein, and Elves: Sushi, Psychedelics, Parallel Universes, and the Quest for Transcendence. Smart Publications. ISBN 978-1-890572-17-4.
^ "Erowid DMT (Dimethyltryptamine) Vault". Erowid.org. Retrieved 20 September 2012.

[1] Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.

[2] Häfelinger G, Nimtz M, Horstmann V, Benz T (1999). "Untersuchungen zur Trifluoracetylierung der Methylderivate von Tryptamin und Serotonin mit verschiedenen Derivatisierungsreagentien: Synthesen, Spektroskopie sowie analytische Trennungen mittels Kapillar-GC" [Trifluoracetylation of methylated derivatives of tryptamine and serotonin by different reagents: synthesis, spectroscopic characterizations, and separations by capillary gas chromatography]. Zeitschrift für Naturforschung B. 54 (3): 397–414. doi:10.1515/znb-1999-0319. S2CID 101000504.

[3] Corothie E, Nakano T (May 1969). "Constituents of the bark of Virola sebifera". Planta Medica. 17 (2): 184–188. doi:10.1055/s-0028-1099844. PMID 5792479. S2CID 43312376.

[auto-4] Carbonaro TM, Gatch MB (September 2016). "Neuropharmacology of N,N-dimethyltryptamine". Brain Research Bulletin. 126 (Pt 1): 74–88. doi:10.1016/j.brainresbull.2016.04.016. PMC 5048497. PMID 27126737.

[McKennaTowers1984-5] McKenna DJ, Towers GH, Abbott F (April 1984). "Monoamine oxidase inhibitors in South American hallucinogenic plants: tryptamine and beta-carboline constituents of ayahuasca". Journal of Ethnopharmacology. 10 (2): 195–223. doi:10.1016/0378-8741(84)90003-5. PMID 6587171.

[6] Haroz R, Greenberg MI (November 2005). "Emerging drugs of abuse". The Medical Clinics of North America. 89 (6): 1259–1276. doi:10.1016/j.mcna.2005.06.008. OCLC 610327022. PMID 16227062.

[Pickover_2005-7] Pickover C (2005). Sex, Drugs, Einstein, and Elves: Sushi, Psychedelics, Parallel Universes, and the Quest for Transcendence. Smart Publications. ISBN 978-1-890572-17-4.

[DMT_Erowid-8] "Erowid DMT (Dimethyltryptamine) Vault". Erowid.org. Retrieved 20 September 2012.

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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)^[1] 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^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
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)^[2] also reported as 80–135 °C (176–275 °F) at 0.03 Torr (4.0 Pa)^[3]
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
(verify)