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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=CC=C2NC=C(CCN(C)C)C2=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
Molecular cloning and expression of a 5-hydroxytryptamine7 serotonin receptor subtype.
1993 Aug 25
Cloning of another human serotonin receptor (5-HT1F): a fifth 5-HT1 receptor subtype coupled to the inhibition of adenylate cyclase.
1993 Jan 15
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
Effects of serotoninergic drugs on tremor induced by physostigmine in rats.
2000 May
Determination of potentially hallucinogenic N-dimethylated indoleamines in human urine by HPLC/ESI-MS-MS.
2001
[(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
Pharmacological characterization of a serotonin receptor (5-HT7) stimulating cAMP production in human corneal epithelial cells.
2003 Nov
The Meixner test in the detection of alpha-amanitin and false-positive reactions caused by psilocin and 5-substituted tryptamines.
2004 Aug
Binding of tryptamine analogs at h5-HT1E receptors: a structure-affinity investigation.
2004 May 15
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
Analysis of hallucinogenic constituents in Amanita mushrooms circulated in Japan.
2006 Dec 20
Pharmacologic analysis of non-synonymous coding h5-HT2A SNPs reveals alterations in atypical antipsychotic and agonist efficacies.
2006 Jan-Feb
Human trabecular meshwork cells express functional serotonin-2A (5HT2A) receptors: role in IOP reduction.
2006 Sep
The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain.
2007 Mar 22
Delta 9-tetrahydrocannabinol-induced catalepsy-like immobilization is mediated by decreased 5-HT neurotransmission in the nucleus accumbens due to the action of glutamate-containing neurons.
2008 Jan 24
Indolealkylamines: biotransformations and potential drug-drug interactions.
2008 Jun
Modification of the effects of 5-methoxy-N,N-dimethyltryptamine on exploratory behavior in rats by monoamine oxidase inhibitors.
2008 Nov
Endogenous hallucinogens as ligands of the trace amine receptors: a possible role in sensory perception.
2009 Jan
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
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 Fri Dec 15 15:15:45 UTC 2023
Edited
by admin
on Fri Dec 15 15:15:45 UTC 2023
Record UNII
X0MKX3GWU9
Record Status Validated (UNII)
Record Version
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Name Type Language
Mebufotenin
INN  
Official Name English
NSC-88624
Code 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 Fri Dec 15 15:15:46 UTC 2023 , Edited by admin on Fri Dec 15 15:15:46 UTC 2023
DEA NO. 7431
Created by admin on Fri Dec 15 15:15:46 UTC 2023 , Edited by admin on Fri Dec 15 15:15:46 UTC 2023
WIKIPEDIA Designer-drugs-5-MeO-DMT
Created by admin on Fri Dec 15 15:15:46 UTC 2023 , Edited by admin on Fri Dec 15 15:15:46 UTC 2023
Code System Code Type Description
WIKIPEDIA
5-MEO-DMT
Created by admin on Fri Dec 15 15:15:46 UTC 2023 , Edited by admin on Fri Dec 15 15:15:46 UTC 2023
PRIMARY
PUBCHEM
1832
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PRIMARY
FDA UNII
X0MKX3GWU9
Created by admin on Fri Dec 15 15:15:46 UTC 2023 , Edited by admin on Fri Dec 15 15:15:46 UTC 2023
PRIMARY
SMS_ID
300000033352
Created by admin on Fri Dec 15 15:15:46 UTC 2023 , Edited by admin on Fri Dec 15 15:15:46 UTC 2023
PRIMARY
CAS
1019-45-0
Created by admin on Fri Dec 15 15:15:46 UTC 2023 , Edited by admin on Fri Dec 15 15:15:46 UTC 2023
PRIMARY
NCI_THESAURUS
C190495
Created by admin on Fri Dec 15 15:15:46 UTC 2023 , Edited by admin on Fri Dec 15 15:15:46 UTC 2023
PRIMARY
NSC
88624
Created by admin on Fri Dec 15 15:15:46 UTC 2023 , Edited by admin on Fri Dec 15 15:15:46 UTC 2023
PRIMARY
DRUG BANK
DB14010
Created by admin on Fri Dec 15 15:15:46 UTC 2023 , Edited by admin on Fri Dec 15 15:15:46 UTC 2023
PRIMARY
CHEBI
2086
Created by admin on Fri Dec 15 15:15:46 UTC 2023 , Edited by admin on Fri Dec 15 15:15:46 UTC 2023
PRIMARY
ECHA (EC/EINECS)
213-813-2
Created by admin on Fri Dec 15 15:15:46 UTC 2023 , Edited by admin on Fri Dec 15 15:15:46 UTC 2023
PRIMARY
EPA CompTox
DTXSID70144324
Created by admin on Fri Dec 15 15:15:46 UTC 2023 , Edited by admin on Fri Dec 15 15:15:46 UTC 2023
PRIMARY
INN
12325
Created by admin on Fri Dec 15 15:15:46 UTC 2023 , Edited by admin on Fri Dec 15 15:15:46 UTC 2023
PRIMARY
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