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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
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
Repeated chlorpromazine administration increases a behavioural response of rats to 5-hydroxytryptamine receptor stimulation.
1977 Feb
[Methylated and unmethylated indolamine in the cisternal fluid in acute endogenous psychoses].
1983
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
Determination of potentially hallucinogenic N-dimethylated indoleamines in human urine by HPLC/ESI-MS-MS.
2001
The role of 5-HT(1A) receptors in control of lower urinary tract function in cats.
2002 Aug 16
Evaluation of the ocular hypotensive response of serotonin 5-HT1A and 5-HT2 receptor ligands in conscious ocular hypertensive cynomolgus monkeys.
2003 Jul
Identification of cytokinins produced by the plant parasitic nematodes Heterodera schachtii and Meloidogyne incognita.
2003 Jul 1
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
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
A demand for clarity regarding a case report on the ingestion of 5-methoxy-N, N-dimethyltryptamine (5-MeO-DMT) in an Ayahuasca preparation.
2006 Jul-Aug
Human trabecular meshwork cells express functional serotonin-2A (5HT2A) receptors: role in IOP reduction.
2006 Sep
In vitro screening of psychoactive drugs by [(35)S]GTPgammaS binding in rat brain membranes.
2007 Dec
The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain.
2007 Mar 22
Comparison of the separation of nine tryptamine standards based on gas chromatography, high performance liquid chromatography and capillary electrophoresis methods.
2008 Feb 15
Neurobiology of spirituality.
2008 Jan
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
Solubilization of 5-methoxy tryptamine molecular probes in CTAB and SDS micelles: a cmc and binding constant study.
2008 Mar
Human and mouse trace amine-associated receptor 1 have distinct pharmacology towards endogenous monoamines and imidazoline receptor ligands.
2009 Oct 23
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
Early-life treatment of antiserotonin antibodies alters sensitivity to serotonin receptors, nociceptive stimulus and serotonin metabolism in adult rats.
2010 Jun
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
Intrahippocampal LSD accelerates learning and desensitizes the 5-HT(2A) receptor in the rabbit, Romano et al.
2010 Oct
The hallucinogenic world of tryptamines: an updated review.
2015 Aug
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.
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
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DEA NO. 7431
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WIKIPEDIA Designer-drugs-5-MeO-DMT
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Code System Code Type Description
WIKIPEDIA
5-MEO-DMT
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PRIMARY
PUBCHEM
1832
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FDA UNII
X0MKX3GWU9
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SMS_ID
300000033352
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CAS
1019-45-0
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NCI_THESAURUS
C190495
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NSC
88624
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DRUG BANK
DB14010
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CHEBI
2086
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ECHA (EC/EINECS)
213-813-2
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EPA CompTox
DTXSID70144324
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INN
12325
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