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Substance Name: O-Methylbufotenine
RN: 1019-45-0
UNII: X0MKX3GWU9
InChIKey: ZSTKHSQDNIGFLM-UHFFFAOYSA-N

Note

  • Compounds that contain the biogenic monoamine tryptamine and are substituted with one methoxy group and two methyl groups. Members of this group include several potent serotonergic hallucinogens found in several unrelated plants, skins of certain toads, and in mammalian brains. They are possibly involved in the etiology of schizophrenia.

Molecular Formula

  • C13-H18-N2-O

Molecular Weight

  • 218.2982
 

Classification Code

  • Natural Product
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Names and Synonyms

Results Name

  • O-Methylbufotenine

Name of Substance

  • N,N-Dimethyl-5-methoxytryptamine

MeSH Heading

  • Methoxydimethyltryptamines

Synonyms

  • 3-(2-(N,N-Dimethyl)aminoethyl)-5-methoxyindole
  • 3-(2-Dimethylaminoethyl)-5-methoxyindole
  • 5-22-12-00027 (Beilstein Handbook Reference)
  • 5-MeO-DMT
  • 5-Methoxy-N,N-dimethyl-1H-indole-3-ethanamine
  • 5-Methoxy-N,N-dimethyltryptamine
  • 5-Methoxydimethyltryptamine
  • BRN 0164771
  • Bufotenine, O-methyl-
  • CT 4334
  • EINECS 213-813-2
  • Indole, 3-(2-(dimethylamino)ethyl)-5-methoxy-
  • Indole, 3-(2-(N,N-dimethylamino)ethyl)-5-methoxy-
  • MeODMT
  • Methoxybufotenin
  • Methylbufotenine
  • N,N-Dimethyl-5-methoxytryptamine
  • NSC 88624
  • O-Methylbufotenine
  • UNII-X0MKX3GWU9

Systematic Names

  • 1H-Indole-3-ethanamine, 5-methoxy-N,N-dimethyl- (9CI)
  • 5-Methoxy-N,N-dimethyl-1H-indole-3-ethylamine
  • Indole, 3-(2-(dimethylamino)ethyl)-5-methoxy- (8CI)
  • Indole, 3-(2-(N,N-dimethylamino)ethyl)-5-methoxy-

Registry Numbers

CAS Registry Number

  • 1019-45-0

FDA UNII

  • X0MKX3GWU9

System Generated Number

  • 0001019450

Structure Descriptors

InChI

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

InChIKey

ZSTKHSQDNIGFLM-UHFFFAOYSA-N

Smiles

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 115mg/kg (115mg/kg)   Psychopharmacologia Vol. 16, Pg. 385, 1970.
mouse LDLo subcutaneous 75mg/kg (75mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" Science. Vol. 156, Pg. 970, 1967.