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Substance Name: Harmine
RN: 442-51-3
UNII: 4FHH5G48T7
InChIKey: BXNJHAXVSOCGBA-UHFFFAOYSA-N

Note

  • Alkaloid isolated from seeds of Peganum harmala L., Zygophyllaceae. It is identical to banisterine, or telepathine, from Banisteria caapi and is one of the active ingredients of hallucinogenic drinks made in the western Amazon region from related plants. It has no therapeutic use, but (as banisterine) was hailed as a cure for postencephalitic Parkinson disease in the 1920's.

Molecular Formula

  • C13-H12-N2-O

Molecular Weight

  • 212.2508
 

Classification Codes

  • Central Nervous System Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Hallucinogens
  • Human Data
  • Monoamine Oxidase Inhibitors
  • Natural Product
  • Psychotropic Drugs
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Names and Synonyms

Name of Substance

  • Harmine

MeSH Heading

  • Harmine

Synonyms

  • 1-Methyl-7-methoxy-beta-carboline
  • 5-23-12-00237 (Beilstein Handbook Reference)
  • 6-Methoxyharman
  • 7-Methoxy-1-methyl-9H-pyrido(3,4-b)indole
  • Banisterine
  • BRN 0178813
  • EINECS 207-131-4
  • Harmine
  • Leucoharmine
  • Telepathine
  • UNII-4FHH5G48T7
  • Yageine
  • Yajeine

Systematic Names

  • 9H-Pyrido(3,4-b)indole, 7-methoxy-1-methyl-
  • Harmine

Registry Numbers

CAS Registry Number

  • 442-51-3

FDA UNII

  • 4FHH5G48T7

System Generated Number

  • 0000442513

Structure Descriptors

InChI

1S/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3

InChIKey

BXNJHAXVSOCGBA-UHFFFAOYSA-N

Smiles

Cc1c2c(ccn1)c3ccc(cc3[nH]2)OC

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 10mg/kg (10mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 129, Pg. 133, 1928.
frog LDLo subcutaneous 300mg/kg (300mg/kg)   Quarterly Journal of Pharmacy & Pharmacology. Vol. 9, Pg. 37, 1936.
guinea pig LDLo subcutaneous 100mg/kg (100mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 129, Pg. 133, 1928.
man TDLo intramuscular 3mg/kg (3mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: SLEEP

GASTROINTESTINAL: NAUSEA OR VOMITING
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 129, Pg. 133, 1928.
mouse LD50 subcutaneous 243mg/kg (243mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: EXCITEMENT
Pharmaceutical Chemistry Journal Vol. 10, Pg. 1171, 1976.
mouse LDLo intravenous 50mg/kg (50mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 129, Pg. 133, 1928.
rabbit LDLo intravenous 60mg/kg (60mg/kg) BEHAVIORAL: EXCITEMENT

SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

BEHAVIORAL: ATAXIA
Neuropharmacology. Vol. 10, Pg. 15, 1971.
rabbit LDLo subcutaneous 200mg/kg (200mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 129, Pg. 133, 1928.
rat LD50 subcutaneous 200mg/kg (200mg/kg)   Psychopharmacology Service Center, Bulletin. Vol. 2, Pg. 17, 1963.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 273 deg C   EXP
log P (octanol-water) 3.56 (none)   EXP
Water Solubility 2.680 mg/L 25 EST
Vapor Pressure 6.26E-06 mm Hg 25 EST
Henry's Law Constant 3.13E-11 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.01E-10 cm3/molecule-sec 25 EST

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