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targets (3)
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Identification
Name Dimethyltryptamine
Accession Number DB01488
Type small molecule
Groups illicit, experimental
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names Not Available
Brand mixtures Not Available
Categories
  • Serotonin Antagonists
  • Hallucinogens
  • Serotonin Agonists
CAS number 61-50-7
Weight Average: 188.2688
Monoisotopic: 188.131348522
Chemical Formula C12H16N2
InChI Key InChIKey=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
Plain Text
IUPAC Name
[2-(1H-indol-3-yl)ethyl]dimethylamine
SMILES
CN(C)CCC1=CNC2=CC=CC=C12
Plain Text
Mass Spec show (7.49 KB)
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication Some people use this compound as a psychedelic inducing agent.
Pharmacodynamics Not Available
Mechanism of action DMT acts as a non-selective agonist at most or all of the serotonin receptors.
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
Toxicity Not Available
Affected organisms Not Available
Pathways Not Available
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 46 °C PhysProp
pKa 8.68 MERCK INDEX (1996)
Predicted Properties
Property Value Source
water solubility 1.69e+00 g/l 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 ChemAxon
rotatable bond count 3 ChemAxon
refractivity 60.44 ChemAxon
polarizability 22.32 ChemAxon
References
Synthesis Reference Not 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
Resource Link
KEGG Compound C08302 Link_out
PubChem Compound 6089 Link_out
PubChem Substance 46507463 Link_out
ChemSpider 5864 Link_out
IUPHAR 141 Link_out
Guide to Pharmacology 141 Link_out
Wikipedia http://en.wikipedia.org/wiki/Dimethyltryptamine Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. 5-hydroxytryptamine 6 receptor

Pharmacological action: yes

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 is mediated by G proteins that stimulate adenylate cyclase. It has a high affinity for tricyclic psychotropic drugs

Organism class: human
UniProt ID: P50406 Link_out
Gene: HTR6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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 2A receptor

Pharmacological action: unknown

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. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production

Organism class: human
UniProt ID: P28223 Link_out
Gene: HTR2A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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 1-type opioid receptor

Pharmacological action: unknown
Organism class: human
UniProt ID: Q99720 Link_out
Gene: OPRS1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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 February 08, 2013 16:20