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Substance Name: Harmaline
RN: 304-21-2
UNII: CN58I4TOET
InChIKey: RERZNCLIYCABFS-UHFFFAOYSA-N

Note

  • A beta-carboline alkaloid isolated from seeds of PEGANUM.

Molecular Formula

  • C13-H14-N2-O

Molecular Weight

  • 214.2666
 

Classification Codes

  • Central Nervous System Agents
  • Central Nervous System Stimulants
  • Enzyme Inhibitors
  • Monoamine Oxidase Inhibitors
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Names and Synonyms

Name of Substance

  • Harmaline

MeSH Heading

  • Harmaline

Synonyms

  • 1-Methyl-7-methoxy-3,4-dihydro-beta-carboline
  • 3,4-Dihydro-7-methoxy-1-methyl-9-pyrid(3,4-b)indole
  • 3,4-Dihydro-7-methoxy-1-methyl-9-pyrido(3,4-b)indole
  • 3,4-Dihydroharmine
  • 4,9-Dihydro-7-methoxy-1-methyl-3H-pyrido(3,4-b)indole
  • 5-23-12-00148 (Beilstein Handbook Reference)
  • Armalin
  • BRN 0207310
  • Dihydroharmine
  • EINECS 206-152-6
  • Harmaline
  • Harmalol methyl ether
  • Harmidine
  • Harmine, dihydro-
  • HSDB 7645
  • NSC 407285
  • O-Methylharmalol
  • UNII-CN58I4TOET

Systematic Names

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

Registry Numbers

CAS Registry Number

  • 304-21-2

FDA UNII

  • CN58I4TOET

System Generated Number

  • 0000304212

Structure Descriptors

InChI

1S/C13H14N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-4,7,15H,5-6H2,1-2H3

InChIKey

RERZNCLIYCABFS-UHFFFAOYSA-N

Smiles

c12c3c([nH]c1C(=NCC2)C)cc(cc3)OC

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 subcutaneous 120mg/kg (120mg/kg)   Psychopharmacology Service Center, Bulletin. Vol. 2, Pg. 17, 1963.
rabbit LDLo intravenous 20mg/kg (20mg/kg) SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

BEHAVIORAL: ATAXIA

BEHAVIORAL: EXCITEMENT
Neuropharmacology. Vol. 10, Pg. 15, 1971.
rat LD50 subcutaneous 120mg/kg (120mg/kg)   Veterinary and Human Toxicology. Vol. 33, Pg. 276, 1991.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 250 dec deg C   EXP
log P (octanol-water) 4.640 (none)   EST
Atmospheric OH Rate Constant 2.03E-10 cm3/molecule-sec 25 EST

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