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Also known as: Dimethyltryptamine, 61-50-7, 2-(3-indolyl)ethyldimethylamine, 3-(2-dimethylaminoethyl)indole, N,n-dimethyl-1h-indole-3-ethylamine, 2-(1h-indol-3-yl)-n,n-dimethylethanamine

Molecular Formula

C₁₂H₁₆N₂

Molecular Weight

188.27 g/mol

InChI Key

DMULVCHRPCFFGV-UHFFFAOYSA-N

FDA UNII

WUB601BHAA

An N-methylated indoleamine derivative and serotonergic hallucinogen which occurs naturally and ubiquitously in several plant species including Psychotria veridis. It also occurs in trace amounts in mammalian brain, blood, and urine, and is known to act as an agonist or antagonist of certain SEROTONIN RECEPTORS.

1 2D Structure

Dimethyltryptamine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-(1H-indol-3-yl)-N,N-dimethylethanamine

2.1.2 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

2.1.3 InChI Key

DMULVCHRPCFFGV-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN(C)CCC1=CNC2=CC=CC=C21

2.2 Other Identifiers

2.2.1 UNII

WUB601BHAA

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Dimethyltryptamine

2. N,n Dimethyltryptamine

2.3.2 Depositor-Supplied Synonyms

1. Dimethyltryptamine

2. 61-50-7

3. 2-(3-indolyl)ethyldimethylamine

4. 3-(2-dimethylaminoethyl)indole

5. N,n-dimethyl-1h-indole-3-ethylamine

6. 2-(1h-indol-3-yl)-n,n-dimethylethanamine

7. 1h-indole-3-ethanamine, N,n-dimethyl-

8. Dmt

9. N,n-dimethyl-1h-indole-3-ethanamine

10. 3-[2-(dimethylamino)ethyl]indole

11. Dea No. 7435

12. Wub601bhaa

13. Chembl12420

14. Chebi:28969

15. (2-indol-3-ylethyl)dimethylamine

16. Nsc-63795

17. Indole, 3-(2-(dimethylamino)ethyl)-

18. Indole, 3-[2-(dimethylamino)ethyl]-

19. [2-(1h-indol-3-yl)ethyl]dimethylamine

20. Dmt (psychogenic)

21. [2-(1h-indol-3-yl)-ethyl]-dimethyl-amine

22. (psychogenic)

23. 3-(2-(dimethylamino)ethyl)indole

24. Einecs 200-508-4

25. Unii-wub601bhaa

26. Nsc 63795

27. Brn 0138259

28. Hsdb 8017

29. Indolalkylamine Der

30. 2-(1h-indol-3-yl)-n,n-dimethyl-ethanamine

31. Nn-dimethyltryptamine

32. 1h-indole-3-ethanamine,n,n-dimethyl-

33. Dimethyltryptamine(dmt)

34. (n,n)-dimethyltryptamine

35. N-dimethyltryptamine

36. Gtpl141

37. 3-(dimethylaminoethyl)-indole

38. Schembl335710

39. Dtxsid60110053

40. Dimethyltryptamine [mart.]

41. N,n-dimethyltryptamine, Free Base

42. Zinc897457

43. Dimethyltryptamine [who-dd]

44. N,n-dimethyltryptamine [mi]

45. Nsc63795

46. Wln: T56 Bmj D2n1&1

47. 3-(2-(dimethylamino)ethyl)-indole

48. Bdbm50026868

49. Mfcd00055989

50. Stk370594

51. 3-[2- (dimethylamino)ethyl]-indole

52. Akos005446117

53. Db01488

54. Mb00483

55. 3-(2-dimethylaminoethyl) Indole

56. 2-(1h-indol-3-yl)-ethyl-dimethyl-amine

57. As-47089

58. N,n-dimethyltryptamine, >=97% (hplc)

59. 2-(1h-indol-3-yl)-n,n-dimethylethylamine

60. 1h-indole-3-ethanamine,n,n-dimethyl

61. N,n-dimethyl-1h-indole-3-ethanamine (9ci)

62. 2-(1h-indol-3-yl)-n,n-dimethylethanamine #

63. C08302

64. D-5500

65. 061d507

66. L001288

67. Q407217

68. 2-(1h-indol-3-yl)-n,n-dimethylethanamine (acd/name 4.0)

69. N-(2-(1h-indol-3-yl)ethyl)-n,n-dimethylamine (acd/name 4.0)

70. N,n-dimethyltryptamine (dmt) Solution, 1.0 Mg/ml In Methanol, Certified Reference Material

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₆N₂
Molecular Weight	188.27 g/mol
XLogP3	2.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	3
Exact Mass	188.131348519 g/mol
Monoisotopic Mass	188.131348519 g/mol
Topological Polar Surface Area	19 Å²
Heavy Atom Count	14
Formal Charge	0
Complexity	179
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Some people use this compound as a psychedelic inducing agent.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Hallucinogens

Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations, and other alterations of mood and thinking. Despite the name, the feature that distinguishes these agents from other classes of drugs is their capacity to induce states of altered perception, thought, and feeling that are not experienced otherwise. (See all compounds classified as Hallucinogens.)

Serotonin Antagonists

Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or SEROTONIN RECEPTOR AGONISTS. (See all compounds classified as Serotonin Antagonists.)

Serotonin Receptor Agonists

Endogenous compounds and drugs that bind to and activate SEROTONIN RECEPTORS. Many serotonin receptor agonists are used as ANTIDEPRESSANTS; ANXIOLYTICS; and in the treatment of MIGRAINE DISORDERS. (See all compounds classified as Serotonin Receptor Agonists.)

5.2 Absorption, Distribution and Excretion

(14)C-DMT accumulates in rat brain cortical slices incubated at 37 C. ... Most of the accumulated (14)C-DMT was associated with the cytoplasmic fraction. Of the portion associated with the crude mitochondrial fraction, 54.4% was associated with nerve-ending fraction.

PMID:41604 Sangiah et al; Biol Psychiatry 14 (6): 925-36 (1979)

The hallucinogenic substance N',N'-dimethyltryptamine and its precursor N-methyltryptamine were found in 24-hr specimens of urine from 19 normal human subjects; the mean excretion rates were 386 ng 24 hr(-1) and 856 ng 24 hr(-1) respectively. The urinary excretion of both compounds was unrelated to age, sex, urinary volume, or creatinine, nor was any consistent diurnal pattern observed. Rates for the mono and dimethylated compounds were not correlated. Diet and the intestinal flora were excluded as a source of urinary dimethyltryptamine. Administration to 4 subjects of sufficient ammonium chloride to /decrease/ the /pH/ of the urine caused a transient increase in dimethyltryptamine excretion but no consistent increase in the rate for N-methyltryptamine. Acidification of the urine did not appear to be the determining factor in this result since in one subject the same drop in urinary pH was achieved by feeding methionine without any increase in dimethyltryptamine excretion.

PMID:22091 Oon MC et al; Psychopharmacology (Berl) 54 (2): 171-5 (1977)

... Eighteen volunteers with prior experience in the use of psychedelics received single oral doses of encapsulated freeze-dried ayahuasca (0.6 and 0.85 mg of DMT/kg of body weight) and placebo. Ayahuasca produced significant subjective effects, peaking between 1.5 and 2 hr, involving perceptual modifications and increases in ratings of positive mood and activation. ...Cmax values for DMT after the low and high ayahuasca doses were 12.14 ng/mL and 17.44 ng/mL, respectively. Tmax (median) was observed at 1.5 hr after both doses. The Tmax for DMT coincided with the peak of subjective effects. ...

PMID:12660312 Riba J et al; J Pharmacol Exp Ther 306 (1): 73-83 (2003)

The endogenous hallucinogen, N,N-dimethyltryptamine (DMT), was labeled with (11)C and its regional distribution in rat brain studied. (11)C-DMT showed higher accumulation in the cerebral cortex, caudate putamen, and amygdaloid nuclei. Studies of the subcellular distribution of (11)C-DMT revealed the specific localization in the fractions enriched with serotonin receptors only when a very low dose was injected into rats. ...

PMID:3489620 Yanai K et al; Eur J Nucl Med 12 (3): 141-6 (1986)

For more Absorption, Distribution and Excretion (Complete) data for N,N-Dimethyltryptamine (8 total), please visit the HSDB record page.

5.3 Metabolism/Metabolites

Following intraperitoneal administration, 5-methoxy-N,N-dimethyltryptamine and N,N-dimethyltryptamine are subject to both a very rapid uptake into, and clearance from, all tissues examined. The current studies in vivo confirm previous in vitro observations that the routes involved in the metabolism of these compounds include oxidative deamination, N-demethylation, O-demethylation, and N-oxidation. The analysis of metabolic profiles in various tissues led to the identification of the N-oxides as major metabolites...

PMID:3472526 Sitaram BR et al; Biochem Pharmacol 36 (9): 1509-12 (1987)

... /From/ ... urine samples collected from three individuals that were administered ayahuasca ... /authors/ show that the major metabolite of the hallucinogenic component of ayahuasca, N,N-dimethyltryptamine (DMT), is the corresponding N-oxide... Further, very little DMT was detected in urine, despite the inhibition of monoamine oxidase afforded by the presence of the harmala alkaloids in ayahuasca. ...

PMID:21058415 McIlhenny EH et al; Biomed Chromatogr 25 (9): 970-84 (2011)

Behavioral aspects and metabolic fate of N,N-dimethyltryptamine (DMT) were studied in mice pretreated with beta-diethylaminoethyl-diphenylpropylacetate (SKF 525-A), iproniazid or chlorpromazine (CPZ.). ... Dose-dependent increases with rapid uptake and disappearance in the brain, plasma and hepatic levels of DMT were measured with doses of 10 and 25 mg/kg DMT. ... It is concluded that DMT is metabolized chiefly by monoamine oxidase rather than by drug-metabolizing hepatic microsomal enzymes and that DMT-induced behavioral effects are due to the parent compound rather than its metabolite.

PMID:276891 Shah NS, Hedden MP; Pharmacol Biochem Behav 8 (4): 351-6 (1978)

Studies were conducted using tritiated DMT and DMT-N-oxide (DMT-NO), and metabolites were identified and quantified using thin-layer chromatography and liquid scintillation counting techniques. Metabolite confirmation was obtained by incubation of alpha,alpha,beta,beta-tetradeutero-DMT (DDMT) with whole brain homogenate followed by combined gas chromatographic/mass spectrometric analyses. The metabolites of DMT were identified as indoleacetic acid (IAA), DMT-NO, N-methyltryptamine (NMT), 2-methyl-1,2,3,4-tetrahydro-beta-carboline (2-MTHBC), tryptamine (TA) and 1,2,3,4- tetrahydro-beta-carboline (THBC). DMT-NO was metabolized to give DMT, NMT, IAA and 2-MTHBC. Formation of these metabolites from DMT-NO was stimulated by anaerobic incubation. ...

PMID:6770869 Barker et al; Biochem Pharmacol 29 (7): 1049-57 (1980)

5.4 Mechanism of Action

DMT acts as a non-selective agonist at most or all of the serotonin receptors.

N,N-dimethyltryptamine (DMT) is a hallucinogen found endogenously in human brain that is commonly recognized to target the 5-hydroxytryptamine 2A receptor or the trace amine-associated receptor to exert its psychedelic effect. DMT has been recently shown to bind sigma-1 receptors, which are ligand-regulated molecular chaperones whose function includes inhibiting various voltage-sensitive ion channels. Thus, it is possible that the psychedelic action of DMT might be mediated in part through sigma-1 receptors. ...

PMID:19278957 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3155724 Su TP et al; Sci Signal 2 (61): pe12 (2009)

The psychotomimetic agent dimethyltryptamine (DMT) has been identified as an endogenous compound in the central nervous system of rodents using a sensitive electron capture gas chromatographic technique. DMT along with its proposed precursor, tryptamine, were identified and quantitated as the heptafluorobutyryl derivatives. A specific high affinity binding site on synaptosomal membranes has been proposed for DMT. This proposal is based on equilibrium dialysis experiments which indicate that DMT at a concentration of 1X10-5M will displace d-LSD on isolated membranes but will not displace bound serotonin at the same concentration. When DMT interacts with the synaptosomal membranes at a concentration of 5X10-10M, the membrane-bound enzyme adenylate cyclase is stimulated such that adenosine3', 5'-monophosphate (cAMP) is produced at a rate of 100 pM/min/mg of protein (2.3 times the endogenous rate). It has also been shown that its presumed precursor, tryptamine, inhibits this process. ... From data obtained in this study it has been postulated that DMT may have in vivo activity similar to those proposed for neurotransmitters or other neuroregulatory agents. ...

PMID:20877 Christian ST et al; Biochem Med 18(2) : 164-83 (1977)

The interactions of the indolealkylamine N,N-dimethyltryptamine (DMT) with 5-hydroxytryptamine1A (5-HT1A) and 5-HT2 receptors in rat brain were analyzed using radioligand binding techniques and biochemical functional assays. The affinity of DMT for 5-HT1A sites labeled by (3)H-8-hydroxy-2-(di-n-propylamino)tetralin (3)H-8-OH-DPAT) was decreased in the presence of 1X10-4 M GTP, suggesting agonist activity of DMT at this receptor. Adenylate cyclase studies in rat hippocampi showed that DMT inhibited forskolin-stimulated cyclase activity, a 5-HT1A agonist effect. DMT displayed full agonist activity with an EC50 of 4X10-6 M in the cyclase assay. In contrast to the agonist actions of DMT at 5-HT1A receptors, DMT appeared to have antagonistic properties at 5-HT2 receptors. The ability of DMT to compete for (3)H-ketanserin-labeled 5-HT2 receptors was not affected by the presence of 1X10-4 M GTP, suggesting antagonist activity of DMT at 5-HT2 receptors. In addition, DMT antagonized 5-HT2-receptor-mediated phosphatidylinositol (PI) turnover in rat cortex at concentrations above 1X10-7 M, with 70% of the 5-HT-induced PI response inhibited at 1X10-4 M DMT. Micromolar concentrations of DMT produced a slight PI stimulation that was not blocked by the 5-HT2 antagonist ketanserin. These studies suggest that DMT has opposing actions on 5-HT receptor subtypes, displaying agonist activity at 5-HT1A receptors and antagonist activity at 5-HT2 receptors.

PMID:1828347 Deliganis AV et al; Biochem Pharmacol 41 (11): 1739-44 (1991)

... The sigma-1 receptor pharmacophore includes an alkylamine core, also found in the endogenous compound N,N-dimethyltryptamine (DMT). DMT acts as a hallucinogen, but its receptor target has been unclear. DMT bound to sigma-1 receptors and inhibited voltage-gated sodium ion (Na+) channels in both native cardiac myocytes and heterologous cells that express sigma-1 receptors. ... DMT induced hypermobility in wild-type mice but not in sigma-1 receptor knockout mice. These biochemical, physiological, and behavioral experiments indicate that DMT is an endogenous agonist for the sigma-1 receptor.

PMID:19213917 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2947205 Fontanilla D et al; Science 323 (5916): 934-7 (2009)

For more Mechanism of Action (Complete) data for N,N-Dimethyltryptamine (7 total), please visit the HSDB record page.

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Cayman Pharma, a leading European provider of cGMP prostaglandin APIs, was formed in 2006 through the merger of Cayman Chemical and NeraPharm, both with vast expertise in prostaglandin chemistry. With almost 60 years of experience, Cayman Pharma owns and uses a patented route for the prostaglandin core structure and has received GMP approvals from European and US regulatory agencies. The company offers validated GMP routes and regulatory approvals for various therapeutic areas, including fertility, eye care, glaucoma and pulmonary hypertension, enabling the development and market launch of its products.

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Laboratorium Ofichem B.V

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Laboratorium Ofichem is a GMP-certified and FDA-approved API manufacturer with state-of-the-art development and production facilities in the Netherlands. We develop and manufacture small molecule APIs in a cost-effective, robust, and compliant way. We have our own portfolio of generic APIs, but we also operate as a CDMO for a wide range of customers. We are a stable family-owned business and with nearly 50 years of experience we have a long history of regulatory compliance and a strong reputation for reliability and quality.

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