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Details

Stereochemistry ACHIRAL
Molecular Formula C13H18N2O
Molecular Weight 218.2948
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Mebufotenin

SMILES

COC1=CC2=C(NC=C2CCN(C)C)C=C1

InChI

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

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

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
[(3)H]-serotonin release from bovine iris-ciliary body: pharmacology of prejunctional serotonin (5-HT(7)) autoreceptors.
2001 Jul
The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain.
2007 Mar 22
A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation.
2008 Jan 15
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
Psychedelic 5-methoxy-N,N-dimethyltryptamine: metabolism, pharmacokinetics, drug interactions, and pharmacological actions.
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 Mon Mar 31 17:52:02 GMT 2025
Edited
by admin
on Mon Mar 31 17:52:02 GMT 2025
Record UNII
X0MKX3GWU9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NSC-88624
Preferred Name English
Mebufotenin
INN  
Official Name English
mebufotenin [INN]
Common Name English
5-Methoxydimethyltryptamine
Common Name English
3-(2-DIMETHYLAMINOETHYL)-5-METHOXYINDOLE
Systematic Name English
2-(5-methoxy-1H-indol-3-yl)-N,N-dimethylethan-1-amine
Systematic Name English
5-METHOXY-N-DIMETHYLTRYPTAMINE
Common Name English
5-METHOXY-N,N-DIMETHYLTRYPTAMINE
Systematic Name English
5-MEO-DMT
Common Name English
N,N-DIMETHYL-5-METHOXYTRYPTAMINE
Systematic Name English
Classification Tree Code System Code
WIKIPEDIA TiHKAL
Created by admin on Mon Mar 31 17:52:02 GMT 2025 , Edited by admin on Mon Mar 31 17:52:02 GMT 2025
DEA NO. 7431
Created by admin on Mon Mar 31 17:52:02 GMT 2025 , Edited by admin on Mon Mar 31 17:52:02 GMT 2025
WIKIPEDIA Designer-drugs-5-MeO-DMT
Created by admin on Mon Mar 31 17:52:02 GMT 2025 , Edited by admin on Mon Mar 31 17:52:02 GMT 2025
Code System Code Type Description
WIKIPEDIA
5-MEO-DMT
Created by admin on Mon Mar 31 17:52:02 GMT 2025 , Edited by admin on Mon Mar 31 17:52:02 GMT 2025
PRIMARY
PUBCHEM
1832
Created by admin on Mon Mar 31 17:52:02 GMT 2025 , Edited by admin on Mon Mar 31 17:52:02 GMT 2025
PRIMARY
FDA UNII
X0MKX3GWU9
Created by admin on Mon Mar 31 17:52:02 GMT 2025 , Edited by admin on Mon Mar 31 17:52:02 GMT 2025
PRIMARY
SMS_ID
300000033352
Created by admin on Mon Mar 31 17:52:02 GMT 2025 , Edited by admin on Mon Mar 31 17:52:02 GMT 2025
PRIMARY
CAS
1019-45-0
Created by admin on Mon Mar 31 17:52:02 GMT 2025 , Edited by admin on Mon Mar 31 17:52:02 GMT 2025
PRIMARY
NCI_THESAURUS
C190495
Created by admin on Mon Mar 31 17:52:02 GMT 2025 , Edited by admin on Mon Mar 31 17:52:02 GMT 2025
PRIMARY
NSC
88624
Created by admin on Mon Mar 31 17:52:02 GMT 2025 , Edited by admin on Mon Mar 31 17:52:02 GMT 2025
PRIMARY
DRUG BANK
DB14010
Created by admin on Mon Mar 31 17:52:02 GMT 2025 , Edited by admin on Mon Mar 31 17:52:02 GMT 2025
PRIMARY
CHEBI
2086
Created by admin on Mon Mar 31 17:52:02 GMT 2025 , Edited by admin on Mon Mar 31 17:52:02 GMT 2025
PRIMARY
ECHA (EC/EINECS)
213-813-2
Created by admin on Mon Mar 31 17:52:02 GMT 2025 , Edited by admin on Mon Mar 31 17:52:02 GMT 2025
PRIMARY
EPA CompTox
DTXSID70144324
Created by admin on Mon Mar 31 17:52:02 GMT 2025 , Edited by admin on Mon Mar 31 17:52:02 GMT 2025
PRIMARY
INN
12325
Created by admin on Mon Mar 31 17:52:02 GMT 2025 , Edited by admin on Mon Mar 31 17:52:02 GMT 2025
PRIMARY
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