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Details

Stereochemistry ACHIRAL
Molecular Formula C13H18N2O.C4H6O4
Molecular Weight 336.3829
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Mebufotenin succinate

SMILES

OC(=O)CCC(O)=O.COC1=CC2=C(NC=C2CCN(C)C)C=C1

InChI

InChIKey=QGPJMYNZUUBWLQ-UHFFFAOYSA-N
InChI=1S/C13H18N2O.C4H6O4/c1-15(2)7-6-10-9-14-13-5-4-11(16-3)8-12(10)13;5-3(6)1-2-4(7)8/h4-5,8-9,14H,6-7H2,1-3H3;1-2H2,(H,5,6)(H,7,8)

HIDE SMILES / InChI

Molecular Formula C4H6O4
Molecular Weight 118.088
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
Molecular cloning and expression of a 5-hydroxytryptamine7 serotonin receptor subtype.
1993 Aug 25
Effects of serotoninergic drugs on tremor induced by physostigmine in rats.
2000 May
[(3)H]-serotonin release from bovine iris-ciliary body: pharmacology of prejunctional serotonin (5-HT(7)) autoreceptors.
2001 Jul
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
Mechanism of action of aripiprazole predicts clinical efficacy and a favourable side-effect profile.
2004 Sep
Suppressive effects of isorhynchophylline on 5-HT2A receptor function in the brain: behavioural and electrophysiological studies.
2005 Jul 11
Pharmacologic analysis of non-synonymous coding h5-HT2A SNPs reveals alterations in atypical antipsychotic and agonist efficacies.
2006 Jan-Feb
In vitro screening of psychoactive drugs by [(35)S]GTPgammaS binding in rat brain membranes.
2007 Dec
Human and mouse trace amine-associated receptor 1 have distinct pharmacology towards endogenous monoamines and imidazoline receptor ligands.
2009 Oct 23
Intrahippocampal LSD accelerates learning and desensitizes the 5-HT(2A) receptor in the rabbit, Romano et al.
2010 Oct
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 14:33:36 GMT 2025
Edited
by admin
on Wed Apr 02 14:33:36 GMT 2025
Record UNII
BN4EF8WH5L
Record Status Validated (UNII)
Record Version
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Name Type Language
Mebufotenin succinate
Common Name English
5-methoxydimethyltryptamine succinate
Preferred Name English
Butanedioic acid, compd. with 5-methoxy-N,N-dimethyl-1H-indole-3-ethanamine (1:1)
Systematic Name English
3-[2-(Dimethylamino)ethyl]-5-methoxyindole succinate
Systematic Name English
Code System Code Type Description
FDA UNII
BN4EF8WH5L
Created by admin on Wed Apr 02 14:33:36 GMT 2025 , Edited by admin on Wed Apr 02 14:33:36 GMT 2025
PRIMARY
CAS
2568048-63-3
Created by admin on Wed Apr 02 14:33:36 GMT 2025 , Edited by admin on Wed Apr 02 14:33:36 GMT 2025
PRIMARY
PUBCHEM
164886348
Created by admin on Wed Apr 02 14:33:36 GMT 2025 , Edited by admin on Wed Apr 02 14:33:36 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE