Details
Stereochemistry | ACHIRAL |
Molecular Formula | C13H18N2O.C7H6O2 |
Molecular Weight | 340.4162 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)C1=CC=CC=C1.COC2=CC3=C(NC=C3CCN(C)C)C=C2
InChI
InChIKey=ZDRGFCJVIIDWMH-UHFFFAOYSA-N
InChI=1S/C13H18N2O.C7H6O2/c1-15(2)7-6-10-9-14-13-5-4-11(16-3)8-12(10)13;8-7(9)6-4-2-1-3-5-6/h4-5,8-9,14H,6-7H2,1-3H3;1-5H,(H,8,9)
Molecular Formula | C7H6O2 |
Molecular Weight | 122.1213 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C13H18N2O |
Molecular Weight | 218.2948 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
N,N-Dimethyl-5-Methoxytryptamine (aka 5-MeO-DMT) is a psychedelic of the tryptamine class. It is found in a wide variety of plant species, and a single psychoactive toad species, the Colorado River toad. Like its close relatives DMT and bufotenin (5-HO-DMT), it has been used as an entheogen in South America. It can also be found in the dart poison traditionally used by the Yanoama Indians of Upper Orinoco. It acts as a non-selective serotonin (5-HT) agonist. -MeO-DMT is O-demethylated by polymorphic cytochrome P450 2D6 (CYP2D6) to an active metabolite, bufotenine. 5-MeO-DMT is classified as a controlled substance in China, Australia, Sweden, Turkey, and the USA.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2096904 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20942780 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Determination of potentially hallucinogenic N-dimethylated indoleamines in human urine by HPLC/ESI-MS-MS. | 2001 |
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Screening for endogenous substrates reveals that CYP2D6 is a 5-methoxyindolethylamine O-demethylase. | 2003 Jun |
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Pharmacologic analysis of non-synonymous coding h5-HT2A SNPs reveals alterations in atypical antipsychotic and agonist efficacies. | 2006 Jan-Feb |
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Comparison of the separation of nine tryptamine standards based on gas chromatography, high performance liquid chromatography and capillary electrophoresis methods. | 2008 Feb 15 |
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A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation. | 2008 Jan 15 |
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Human and mouse trace amine-associated receptor 1 have distinct pharmacology towards endogenous monoamines and imidazoline receptor ligands. | 2009 Oct 23 |
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LSD but not lisuride disrupts prepulse inhibition in rats by activating the 5-HT(2A) receptor. | 2010 Feb |
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Early-life treatment of antiserotonin antibodies alters sensitivity to serotonin receptors, nociceptive stimulus and serotonin metabolism in adult rats. | 2010 Jun |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20942780
10 mg of 5-MeO-DMT administrated intranasally or sublingually causes a significant visionary response.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18057721
Membranes were prepared from the cerebral cortex and striatum of Male SD rats and maintained in HEPES buffer pH 7.6, 20 mM HEPES, 7 mM MgCl2, 100 mM NaCl, 1 mM EDTA, 0.2 mM dithiothreitol (DTT). Cells were plated in 96 wells containing an assay buffer of 25 mM HEPES, pH 7.6, 7 mM MgCl2, 100 mM NaCl, 1 mM EDTA, 0.2 mM DTT and 10 mM DPCPX. Each well also received various concentrations screening compounds, DA, 5-HT, NE, and the mixture of brain membranes (2 mg protein/well for the striatum and 4 mg protein/well for the cortex) and 150 micro-M GDP. This mixture was pre-incubated at 30 °C for 20 minutes with shaking. Incubation was started by adding 0.1 nM [35S]GTPgS to a total volume of 100 mL and continued at 30 °C for 90 minutes with shaking. The reaction was stopped by rapid filtration and retained membrane-bound radioactivity on the filter was measured by liquid scintillation counting. 5-MeODMT was found to have an EC50 of 3.8 x 10^07 M.
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 17:49:38 GMT 2025
by
admin
on
Wed Apr 02 17:49:38 GMT 2025
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Record UNII |
MF2UDH4QUF
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Record Status |
Validated (UNII)
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Record Version |
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