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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=CC=C3NC=C(CCN(C)C)C3=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 C13H18N2O
Molecular Weight 218.2948
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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
Identification of residues in transmembrane regions III and VI that contribute to the ligand binding site of the serotonin 5-HT6 receptor.
1998 Nov
High-affinity agonist binding correlates with efficacy (intrinsic activity) at the human serotonin 5-HT2A and 5-HT2C receptors: evidence favoring the ternary complex and two-state models of agonist action.
1999 May
Pharmepéna-Psychonautics: Human intranasal, sublingual and oral pharmacology of 5-methoxy-N,N-dimethyl-tryptamine.
2001 Oct-Dec
Evaluation of the ocular hypotensive response of serotonin 5-HT1A and 5-HT2 receptor ligands in conscious ocular hypertensive cynomolgus monkeys.
2003 Jul
Binding of tryptamine analogs at h5-HT1E receptors: a structure-affinity investigation.
2004 May 15
Mechanism of action of aripiprazole predicts clinical efficacy and a favourable side-effect profile.
2004 Sep
The rapid analysis of heroin drug seizures using micellar electrokinetic chromatography with short-end injection.
2005 Jan
A fatal intoxication following the ingestion of 5-methoxy-N,N-dimethyltryptamine in an ayahuasca preparation.
2005 Nov-Dec
The roles of 5-HT1A and 5-HT2 receptors in the effects of 5-MeO-DMT on locomotor activity and prepulse inhibition in rats.
2006 Dec
Efficient and sensitive method for quantitative analysis of alkaloids in hardinggrass (Phalaris aquatica L.).
2006 Dec 13
A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation.
2008 Jan 15
Schedules of controlled substances: placement of 5-methoxy-N,N-dimethyltryptamine into Schedule I of the Controlled Substances Act. Final rule.
2010 Dec 20
LSD but not lisuride disrupts prepulse inhibition in rats by activating the 5-HT(2A) receptor.
2010 Feb
Effects of monoamine oxidase inhibitor and cytochrome P450 2D6 status on 5-methoxy-N,N-dimethyltryptamine metabolism and pharmacokinetics.
2010 Jul 1
Hearing loss alters serotonergic modulation of intrinsic excitability in auditory cortex.
2010 Nov
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 Sat Dec 16 19:56:36 UTC 2023
Edited
by admin
on Sat Dec 16 19:56:36 UTC 2023
Record UNII
MF2UDH4QUF
Record Status Validated (UNII)
Record Version
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Name Type Language
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
5-MeO-DMT benzoate
Common 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 Sat Dec 16 19:56:36 UTC 2023 , Edited by admin on Sat Dec 16 19:56:36 UTC 2023
PRIMARY
CAS
282103-25-7
Created by admin on Sat Dec 16 19:56:36 UTC 2023 , Edited by admin on Sat Dec 16 19:56:36 UTC 2023
PRIMARY
PUBCHEM
44783953
Created by admin on Sat Dec 16 19:56:36 UTC 2023 , Edited by admin on Sat Dec 16 19:56:36 UTC 2023
PRIMARY
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