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Identification
NameDimethyltryptamine
Accession NumberDB01488
Typesmall molecule
Groupsexperimental, illicit
Description

An N-methylated indoleamine derivative, a serotonergic hallucinogen found in several plants, especially Prestonia amazonica (Apocynaceae) and in mammalian brain, blood, and urine. It apparently acts as an agonist at some types of serotonin receptors and an antagonist at others. [PubChem]

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number61-50-7
WeightAverage: 188.2688
Monoisotopic: 188.131348522
Chemical FormulaC12H16N2
InChI KeyInChIKey=DMULVCHRPCFFGV-UHFFFAOYSA-N
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
IUPAC Name
[2-(1H-indol-3-yl)ethyl]dimethylamine
SMILES
CN(C)CCC1=CNC2=CC=CC=C12
Mass Specshow(7.49 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassIndoles and Derivatives
SubclassTryptamines and Derivatives
Direct parentTryptamines and Derivatives
Alternative parentsIndoles; Substituted Pyrroles; Benzene and Substituted Derivatives; Tertiary Amines; Polyamines
Substituentsindole; benzene; substituted pyrrole; pyrrole; tertiary amine; polyamine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the tryptamines and derivatives. These are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring subsituted at the thrid position by an ethanamine.
Pharmacology
IndicationSome people use this compound as a psychedelic inducing agent.
PharmacodynamicsNot Available
Mechanism of actionDMT acts as a non-selective agonist at most or all of the serotonin receptors.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 1.0
Blood Brain Barrier + 0.9797
Caco-2 permeable + 0.6601
P-glycoprotein substrate Substrate 0.634
P-glycoprotein inhibitor I Non-inhibitor 0.9304
P-glycoprotein inhibitor II Non-inhibitor 0.6713
Renal organic cation transporter Inhibitor 0.7268
CYP450 2C9 substrate Non-substrate 0.8154
CYP450 2D6 substrate Substrate 0.5974
CYP450 3A4 substrate Substrate 0.5824
CYP450 1A2 substrate Non-inhibitor 0.8597
CYP450 2C9 substrate Non-inhibitor 0.9436
CYP450 2D6 substrate Non-inhibitor 0.8744
CYP450 2C19 substrate Non-inhibitor 0.917
CYP450 3A4 substrate Non-inhibitor 0.843
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8954
Ames test AMES toxic 0.52
Carcinogenicity Non-carcinogens 0.9588
Biodegradation Not ready biodegradable 0.9795
Rat acute toxicity 2.6187 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8972
hERG inhibition (predictor II) Non-inhibitor 0.7733
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point46 °CPhysProp
pKa8.68MERCK INDEX (1996)
Predicted Properties
PropertyValueSource
water solubility1.69e+00 g/lALOGPS
logP2.41ALOGPS
logP2.3ChemAxon
logS-2ALOGPS
pKa (strongest acidic)17.16ChemAxon
pKa (strongest basic)9.55ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count1ChemAxon
polar surface area19.03ChemAxon
rotatable bond count3ChemAxon
refractivity60.44ChemAxon
polarizability22.32ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. Strassman RJ, Qualls CR: Dose-response study of N,N-dimethyltryptamine in humans. I. Neuroendocrine, autonomic, and cardiovascular effects. Arch Gen Psychiatry. 1994 Feb;51(2):85-97. Pubmed
  2. Callaway JC: A proposed mechanism for the visions of dream sleep. Med Hypotheses. 1988 Jun;26(2):119-24. Pubmed
External Links
ResourceLink
KEGG CompoundC08302
PubChem Compound6089
PubChem Substance46507463
ChemSpider5864
IUPHAR141
Guide to Pharmacology141
WikipediaDimethyltryptamine
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. 5-hydroxytryptamine receptor 6

Kind: protein

Organism: Human

Pharmacological action: yes

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 6 P50406 Details

References:

  1. Glennon RA, Lee M, Rangisetty JB, Dukat M, Roth BL, Savage JE, McBride A, Rauser L, Hufeisen S, Lee DK: 2-Substituted tryptamines: agents with selectivity for 5-HT serotonin receptors. J Med Chem. 2000 Mar 9;43(5):1011-8. Pubmed
  2. Nyandege A, Kolanos R, Roth BL, Glennon RA: Further studies on the binding of N1-substituted tryptamines at h5-HT6 receptors. Bioorg Med Chem Lett. 2007 Mar 15;17(6):1691-4. Epub 2007 Jan 4. Pubmed
  3. Glennon RA, Gessner PK: The electronic and serotonin receptor binding affinity properties of N,N-dimethyltryptamine analogs. Res Commun Chem Pathol Pharmacol. 1977 Nov;18(3):453-65. Pubmed
  4. Glennon RA, Liebowitz SM, Mack EC: Serotonin receptor binding affinities of several hallucinogenic phenylalkylamine and N,N-dimethyltryptamine analogues. J Med Chem. 1978 Aug;21(8):822-5. Pubmed

2. 5-hydroxytryptamine receptor 2A

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 2A P28223 Details

References:

  1. Pierce PA, Peroutka SJ: Hallucinogenic drug interactions with neurotransmitter receptor binding sites in human cortex. Psychopharmacology (Berl). 1989;97(1):118-22. Pubmed
  2. Su TP, Hayashi T, Vaupel DB: When the endogenous hallucinogenic trace amine N,N-dimethyltryptamine meets the sigma-1 receptor. Sci Signal. 2009 Mar 10;2(61):pe12. Pubmed

3. Sigma non-opioid intracellular receptor 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Sigma non-opioid intracellular receptor 1 Q99720 Details

References:

  1. Su TP, Hayashi T, Vaupel DB: When the endogenous hallucinogenic trace amine N,N-dimethyltryptamine meets the sigma-1 receptor. Sci Signal. 2009 Mar 10;2(61):pe12. Pubmed

Comments
Drug created on July 31, 2007 07:09 / Updated on September 16, 2013 17:14