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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
Structure of Mebufotenin benzoate

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)

HIDE SMILES / InChI

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Determination of potentially hallucinogenic N-dimethylated indoleamines in human urine by HPLC/ESI-MS-MS.
2001
Screening for endogenous substrates reveals that CYP2D6 is a 5-methoxyindolethylamine O-demethylase.
2003 Jun
Pharmacologic analysis of non-synonymous coding h5-HT2A SNPs reveals alterations in atypical antipsychotic and agonist efficacies.
2006 Jan-Feb
Comparison of the separation of nine tryptamine standards based on gas chromatography, high performance liquid chromatography and capillary electrophoresis methods.
2008 Feb 15
A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation.
2008 Jan 15
Human and mouse trace amine-associated receptor 1 have distinct pharmacology towards endogenous monoamines and imidazoline receptor ligands.
2009 Oct 23
LSD but not lisuride disrupts prepulse inhibition in rats by activating the 5-HT(2A) receptor.
2010 Feb
Early-life treatment of antiserotonin antibodies alters sensitivity to serotonin receptors, nociceptive stimulus and serotonin metabolism in adult rats.
2010 Jun
Patents

Sample Use Guides

10 mg of 5-MeO-DMT administrated intranasally or sublingually causes a significant visionary response.
Route of Administration: Other
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 Wed Apr 02 17:49:38 GMT 2025
Edited
by admin
on Wed Apr 02 17:49:38 GMT 2025
Record UNII
MF2UDH4QUF
Record Status Validated (UNII)
Record Version
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Name Type Language
5-MeO-DMT benzoate
Preferred Name English
Mebufotenin benzoate
Common Name English
1H-Indole-3-ethanamine, 5-methoxy-N,N-dimethyl-, benzoate (1:1)
Systematic Name English
Methoxybufotenin benzoate
Common Name English
1H-Indole-3-ethanamine, 5-methoxy-N,N-dimethyl-, monobenzoate
Systematic Name English
N,N-Dimethyl-5-methoxytryptamine benzoate
Common Name English
Methylbufotenine benzoate
Common Name English
Code System Code Type Description
FDA UNII
MF2UDH4QUF
Created by admin on Wed Apr 02 17:49:38 GMT 2025 , Edited by admin on Wed Apr 02 17:49:38 GMT 2025
PRIMARY
SMS_ID
300000047833
Created by admin on Wed Apr 02 17:49:38 GMT 2025 , Edited by admin on Wed Apr 02 17:49:38 GMT 2025
PRIMARY
CAS
282103-25-7
Created by admin on Wed Apr 02 17:49:38 GMT 2025 , Edited by admin on Wed Apr 02 17:49:38 GMT 2025
PRIMARY
PUBCHEM
44783953
Created by admin on Wed Apr 02 17:49:38 GMT 2025 , Edited by admin on Wed Apr 02 17:49:38 GMT 2025
PRIMARY
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