Dimethyltryptamine
Identification
- Generic Name
- Dimethyltryptamine
- DrugBank Accession Number
- DB01488
- Background
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.
- Type
- Small Molecule
- Groups
- Experimental, Illicit
- Structure
Structure for Dimethyltryptamine (DB01488)
- Weight
- Average: 188.2688
Monoisotopic: 188.131348522 - Chemical Formula
- C12H16N2
- Synonyms
- 2-(3-indolyl)ethyldimethylamine
- 3-(2-dimethylaminoethyl)indole
- 3-[2-(dimethylamino)ethyl]indole
- DMT
- N,N-dimethyl-1H-indole-3-ethylamine
- N,N-dimethyltryptamine
- External IDs
- DEA NO. 7435
- NSC-63795
Pharmacology
- Indication
Some people use this compound as a psychedelic inducing agent.
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Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- Pharmacodynamics
Not Available
- Mechanism of action
DMT acts as a non-selective agonist at most or all of the serotonin receptors.
Target Actions Organism A5-hydroxytryptamine receptor 6 Not Available Humans U5-hydroxytryptamine receptor 2A Not Available Humans USigma non-opioid intracellular receptor 1 Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Reduce medical errorsand improve treatment outcomes with our comprehensive & structured data on drug adverse effects.Reduce medical errors & improve treatment outcomes with our adverse effects data- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Dimethyltryptamine is combined with 1,2-Benzodiazepine. Acenocoumarol The risk or severity of adverse effects can be increased when Dimethyltryptamine is combined with Acenocoumarol. Acetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Dimethyltryptamine. Acetophenazine The risk or severity of adverse effects can be increased when Acetophenazine is combined with Dimethyltryptamine. Aclidinium Dimethyltryptamine may increase the central nervous system depressant (CNS depressant) activities of Aclidinium. Agomelatine The risk or severity of adverse effects can be increased when Dimethyltryptamine is combined with Agomelatine. Alfentanil The risk or severity of adverse effects can be increased when Alfentanil is combined with Dimethyltryptamine. Alimemazine The risk or severity of adverse effects can be increased when Alimemazine is combined with Dimethyltryptamine. Almotriptan The risk or severity of adverse effects can be increased when Almotriptan is combined with Dimethyltryptamine. Alosetron The risk or severity of adverse effects can be increased when Alosetron is combined with Dimethyltryptamine. 
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- Not Available
Categories
- Drug Categories
- Amines
- Antidepressive Agents
- Biogenic Amines
- Biogenic Monoamines
- Central Nervous System Agents
- Central Nervous System Depressants
- Hallucinogens
- Heterocyclic Compounds, Fused-Ring
- Indoles
- Neurotransmitter Agents
- Psychotropic Drugs
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin Agents
- Serotonin Receptor Agonists
- Serotonin Receptor Antagonists
- Tryptamines
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as tryptamines and derivatives. These are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Indoles and derivatives
- Sub Class
- Tryptamines and derivatives
- Direct Parent
- Tryptamines and derivatives
- Alternative Parents
- 3-alkylindoles / Aralkylamines / Substituted pyrroles / Benzenoids / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- 3-alkylindole / Amine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Heteroaromatic compound / Hydrocarbon derivative / Indole / Organic nitrogen compound
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- tryptamine alkaloid, tryptamines (CHEBI:28969) / Indole alkaloids (C08302)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- WUB601BHAA
- CAS number
- 61-50-7
- InChI Key
- 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
References
- General References
- 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. [Article]
- Callaway JC: A proposed mechanism for the visions of dream sleep. Med Hypotheses. 1988 Jun;26(2):119-24. [Article]
- External Links
- Human Metabolome Database
- HMDB0005973
- KEGG Compound
- C08302
- PubChem Compound
- 6089
- PubChem Substance
- 46507463
- ChemSpider
- 5864
- BindingDB
- 50026868
- ChEBI
- 28969
- ChEMBL
- CHEMBL12420
- ZINC
- ZINC000000897457
- Guide to Pharmacology
- GtP Drug Page
- Wikipedia
- Dimethyltryptamine
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 1 Completed Treatment Healthy Volunteers 1 1 Not Yet Recruiting Basic Science Healthy Volunteers 1 1 Recruiting Other Depression / Major Depressive Disorder (MDD) 1 1, 2 Recruiting Treatment Depression / Major Depressive Disorder (MDD) / Major depressive disorder, recurrent episode / Treatment Resistant Depression (TRD) 1 1, 2 Recruiting Treatment Major Depressive Disorder (MDD) 1 0 Recruiting Basic Science Cognitive Function 1, Social / Emotions / Empathy / Mood 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 46 °C PhysProp pKa 8.68 MERCK INDEX (1996) - Predicted Properties
Property Value Source Water Solubility 1.69 mg/mL ALOGPS logP 2.41 ALOGPS logP 2.3 ChemAxon logS -2 ALOGPS pKa (Strongest Acidic) 17.16 ChemAxon pKa (Strongest Basic) 9.55 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 1 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 19.03 Å2 ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 60.44 m3·mol-1 ChemAxon Polarizability 22.32 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - 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 inhibitor Non-inhibitor 0.9436 CYP450 2D6 inhibitor Non-inhibitor 0.8744 CYP450 2C19 inhibitor Non-inhibitor 0.917 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Download (7.49 KB)
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available GC-MS Spectrum - EI-B GC-MS splash10-0a4i-9100000000-27639de9acc9e554bfc8 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- General Function
- Serotonin receptor activity
- Specific Function
- This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor ...
- Gene Name
- HTR6
- Uniprot ID
- P50406
- Uniprot Name
- 5-hydroxytryptamine receptor 6
- Molecular Weight
- 46953.625 Da
References
- 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(6) serotonin receptors. J Med Chem. 2000 Mar 9;43(5):1011-8. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Virus receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
- Gene Name
- HTR2A
- Uniprot ID
- P28223
- Uniprot Name
- 5-hydroxytryptamine receptor 2A
- Molecular Weight
- 52602.58 Da
References
- Pierce PA, Peroutka SJ: Hallucinogenic drug interactions with neurotransmitter receptor binding sites in human cortex. Psychopharmacology (Berl). 1989;97(1):118-22. [Article]
- 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. doi: 10.1126/scisignal.261pe12. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Opioid receptor activity
- Specific Function
- Functions in lipid transport from the endoplasmic reticulum and is involved in a wide array of cellular functions probably through regulation of the biogenesis of lipid microdomains at the plasma m...
- Gene Name
- SIGMAR1
- Uniprot ID
- Q99720
- Uniprot Name
- Sigma non-opioid intracellular receptor 1
- Molecular Weight
- 25127.52 Da
References
- 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. doi: 10.1126/scisignal.261pe12. [Article]
Drug created on July 31, 2007 13:09 / Updated on June 12, 2020 16:51