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
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
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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2096904 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20942780 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Repeated chlorpromazine administration increases a behavioural response of rats to 5-hydroxytryptamine receptor stimulation. | 1977 Feb |
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[Methylated and unmethylated indolamine in the cisternal fluid in acute endogenous psychoses]. | 1983 |
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Molecular cloning and expression of a 5-hydroxytryptamine7 serotonin receptor subtype. | 1993 Aug 25 |
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Cloning of another human serotonin receptor (5-HT1F): a fifth 5-HT1 receptor subtype coupled to the inhibition of adenylate cyclase. | 1993 Jan 15 |
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Identification of residues in transmembrane regions III and VI that contribute to the ligand binding site of the serotonin 5-HT6 receptor. | 1998 Nov |
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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 |
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Effects of serotoninergic drugs on tremor induced by physostigmine in rats. | 2000 May |
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[(3)H]-serotonin release from bovine iris-ciliary body: pharmacology of prejunctional serotonin (5-HT(7)) autoreceptors. | 2001 Jul |
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The role of 5-HT(1A) receptors in control of lower urinary tract function in cats. | 2002 Aug 16 |
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Involvement of 5-hydroxytryptamine neuronal system in Delta(9)-tetrahydrocannabinol-induced impairment of spatial memory. | 2002 Jun 12 |
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5-HT2A receptor-stimulated phosphoinositide hydrolysis in the stimulus effects of hallucinogens. | 2002 May |
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The Meixner test in the detection of alpha-amanitin and false-positive reactions caused by psilocin and 5-substituted tryptamines. | 2004 Aug |
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Binding of tryptamine analogs at h5-HT1E receptors: a structure-affinity investigation. | 2004 May 15 |
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Mechanism of action of aripiprazole predicts clinical efficacy and a favourable side-effect profile. | 2004 Sep |
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The rapid analysis of heroin drug seizures using micellar electrokinetic chromatography with short-end injection. | 2005 Jan |
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Suppressive effects of isorhynchophylline on 5-HT2A receptor function in the brain: behavioural and electrophysiological studies. | 2005 Jul 11 |
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A fatal intoxication following the ingestion of 5-methoxy-N,N-dimethyltryptamine in an ayahuasca preparation. | 2005 Nov-Dec |
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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 |
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Efficient and sensitive method for quantitative analysis of alkaloids in hardinggrass (Phalaris aquatica L.). | 2006 Dec 13 |
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Analysis of hallucinogenic constituents in Amanita mushrooms circulated in Japan. | 2006 Dec 20 |
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Pharmacologic analysis of non-synonymous coding h5-HT2A SNPs reveals alterations in atypical antipsychotic and agonist efficacies. | 2006 Jan-Feb |
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The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain. | 2007 Mar 22 |
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Comparison of the separation of nine tryptamine standards based on gas chromatography, high performance liquid chromatography and capillary electrophoresis methods. | 2008 Feb 15 |
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Neurobiology of spirituality. | 2008 Jan |
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Indolealkylamines: biotransformations and potential drug-drug interactions. | 2008 Jun |
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Modification of the effects of 5-methoxy-N,N-dimethyltryptamine on exploratory behavior in rats by monoamine oxidase inhibitors. | 2008 Nov |
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Human and mouse trace amine-associated receptor 1 have distinct pharmacology towards endogenous monoamines and imidazoline receptor ligands. | 2009 Oct 23 |
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Schedules of controlled substances: placement of 5-methoxy-N,N-dimethyltryptamine into Schedule I of the Controlled Substances Act. Final rule. | 2010 Dec 20 |
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LSD but not lisuride disrupts prepulse inhibition in rats by activating the 5-HT(2A) receptor. | 2010 Feb |
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Hearing loss alters serotonergic modulation of intrinsic excitability in auditory cortex. | 2010 Nov |
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Psychedelic 5-methoxy-N,N-dimethyltryptamine: metabolism, pharmacokinetics, drug interactions, and pharmacological actions. | 2010 Oct |
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Intrahippocampal LSD accelerates learning and desensitizes the 5-HT(2A) receptor in the rabbit, Romano et al. | 2010 Oct |
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The hallucinogenic world of tryptamines: an updated review. | 2015 Aug |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20942780
10 mg of 5-MeO-DMT administrated intranasally or sublingually causes a significant visionary response.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18057721
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.
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TiHKAL
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Designer-drugs-5-MeO-DMT
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