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M2381

Sigma-Aldrich

5-Methoxy-N,N-dimethyltryptamine

Synonym(s):

3-(2-Dimethylaminoethyl)-5-methoxyindole, 3-[2-(Dimethylamino)ethyl]-5-methoxyindole, 5-MeO-DMT, 5-Methoxy-DMT, 5-OMe-DMT

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About This Item

Empirical Formula (Hill Notation):
C13H18N2O
CAS Number:
1019-45-0
Molecular Weight:
218.29
EC Number:
213-813-2
MDL number:
MFCD00005658
UNSPSC Code:
41116107
PubChem Substance ID:
24278119

drug control

USDEA Schedule I; Home Office Schedule 1; kontrollierte Droge in Deutschland

mp

69-70 °C (lit.)

storage temp.

2-8°C

SMILES string

COc1ccc2[nH]cc(CCN(C)C)c2c1

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

InChI key

ZSTKHSQDNIGFLM-UHFFFAOYSA-N

Gene Information

human ... HTR1A(3350) , HTR1B(3351) , HTR1D(3352) , HTR1E(3354) , HTR1F(3355) , HTR2A(3356) , HTR2B(3357) , HTR2C(3358) , HTR3A(3359) , HTR3B(9177) , HTR3C(170572) , HTR3D(200909) , HTR3E(285242) , HTR4(3360) , HTR5A(3361) , HTR5B(645694) , HTR6(3362) , HTR7(3363)
rat ... Htr1a(24473) , Htr2a(29595) , Htr2b(29581) , Htr2c(25187) , Htr7(65032)

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Biochem/physiol Actions

Hallucinogen; non-selective serotonin receptor agonist.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H336

Hazard Classifications

STOT SE 3

target_organs

Central nervous system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Thomas S Ray
PloS one, 5(2), e9019-e9019 (2010-02-04)
We currently understand the mental effects of psychedelics to be caused by agonism or partial agonism of 5-HT(2A) (and possibly 5-HT(2C)) receptors, and we understand that psychedelic drugs, especially phenylalkylamines, are fairly selective for these two receptors. This manuscript is
Adam L Halberstadt
Pharmacology, biochemistry, and behavior, 143, 1-10 (2016-01-19)
Monoamine oxidase inhibitors (MAOIs) are often ingested together with tryptamine hallucinogens, but relatively little is known about the consequences of their combined use. We have shown previously that monoamine oxidase-A (MAO-A) inhibitors alter the locomotor profile of the hallucinogen 5-methoxy-N,N-dimethyltryptamine
Rafael Vitor Lima da Cruz et al.
Frontiers in molecular neuroscience, 11, 312-312 (2018-09-21)
The subgranular zone (SGZ) of dentate gyrus (DG) is one of the few regions in which neurogenesis is maintained throughout adulthood. It is believed that newborn neurons in this region encode temporal information about partially overlapping contextual memories. The 5-Methoxy-N,N-dimethyltryptamine
Jessica Winne et al.
Experimental neurology, 326, 113175-113175 (2020-01-11)
Salicylate intoxication is a cause of tinnitus and comorbidly associated with anxiety in humans. In a previous work, we showed that salicylate induces anxiety-like behavior and hippocampal type 2 theta oscillations (theta2) in mice. Here we investigate if the anxiogenic
Vanja Dakic et al.
Scientific reports, 7(1), 12863-12863 (2017-10-11)
Dimethyltryptamines are entheogenic serotonin-like molecules present in traditional Amerindian medicine recently associated with cognitive gains, antidepressant effects, and changes in brain areas related to attention. Legal restrictions and the lack of adequate experimental models have limited the understanding of how
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