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Substance Name: Bufotenin
RN: 487-93-4
UNII: 0A31347TZK
InChIKey: VTTONGPRPXSUTJ-UHFFFAOYSA-N

Note

  • A hallucinogenic serotonin analog found in frog or toad skins, mushrooms, higher plants, and mammals, especially in the brains, plasma, and urine of schizophrenics. Bufotenin has been used as a tool in CNS studies and misused as a psychedelic.

Molecular Formula

  • C12-H16-N2-O

Molecular Weight

  • 204.2714
 

Classification Codes

Classification Codes

  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • Hallucinogens
  • Human Data
  • Neurotransmitter Agents
  • Psychotropic Drugs
  • Serotonin Agents
  • Serotonin Antagonists

Superlist Classification Code

  • DEA Schedule I
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Names and Synonyms

Results Name

  • Bufotenin

Name of Substance

  • Bufotenin
  • Bufotenine

MeSH Heading

  • Bufotenin

Synonyms

  • 3-(2-Dimethylaminoethyl)-5-indolol
  • 3-(beta-Dimethylaminoethyl)-5-hydroxyindole
  • 5-22-12-00026 (Beilstein Handbook Reference)
  • 5-Hydroxy-N,N-dimethyltryptamine
  • BRN 0160628
  • Bufotenin
  • Bufotenine
  • Cinobufotenine
  • Cohoba
  • EINECS 207-667-9
  • Mappin
  • Mappine
  • N,N-Dimethyl-5-hydroxytryptamine
  • N,N-Dimethylserotonin
  • NSC 89593
  • UNII-0A31347TZK

Systematic Names

  • 1H-Indol-5-ol, 3-(2-(dimethylamino)ethyl)-
  • 3-(2-(Dimethylamino)ethyl)-1H-indol-5-ol
  • Indol-5-ol, 3-(2-(dimethylamino)ethyl)-

Superlist Names

  • 3-(2-Dimethylaminoethyl)-5-indolol
  • 3-(beta-Dimethylaminoethyl)-5-hydroxyindole
  • 5-Hydroxy-N,N-dimethyltryptamine
  • Bufotenine
  • DEA No. 7433
  • Mappine
  • N,N-Dimethylserotonin

Registry Numbers

CAS Registry Number

  • 487-93-4

FDA UNII

  • 0A31347TZK

System Generated Number

  • 0000487934

Structure Descriptors

InChI

InChI=1S/C12H16N2O/c1-14(2)6-5-9-8-13-12-4-3-10(15)7-11(9)12/h3-4,7-8,13,15H,5-6H2,1-2H3

InChIKey

VTTONGPRPXSUTJ-UHFFFAOYSA-N

Smiles

CN(C)CCc1c[nH]c2ccc(O)cc12

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
frog LDLo parenteral 2500mg/kg (2500mg/kg) CARDIAC: OTHER CHANGES Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 86, Pg. 138, 1920.
human TDLo intravenous 57ug/kg (0.057mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

PERIPHERAL NERVE AND SENSATION: SENSORY CHANGE INVOLVING PERIPHERAL NERVE

GASTROINTESTINAL: OTHER CHANGES
Science. Vol. 123, Pg. 886, 1956.
mouse LD50 intraperitoneal 290mg/kg (290mg/kg)   Psychopharmacologia Vol. 16, Pg. 385, 1970.
mouse LD50 intravenous 25mg/kg (25mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 64, Pg. 144, 1968.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 146.5 deg C   EXP
log P (octanol-water) 1.460 (none)   EST
Atmospheric OH Rate Constant 2.81E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.