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 about five to fifteen 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)