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Merck
CN

286036

Harmaline

97%

Synonym(s):

1-Methyl-7-methoxy-3,4-dihydro-β-carboline, 3,4-Dihydroharmine, 4,9-Dihydro-7-methoxy-1-methyl-3H-pyrido[3,4-b]indole, Dihydroharmine, Harmalol methyl ether, Harmidine, NSC 407285

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About This Item

Empirical Formula (Hill Notation):
C13H14N2O
CAS Number:
304-21-2
Molecular Weight:
214.26
EC Number:
206-152-6
UNSPSC Code:
12352100
MDL number:
MFCD00004955
Beilstein/REAXYS Number:
207310

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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

InChI key

RERZNCLIYCABFS-UHFFFAOYSA-N

SMILES string

COc1ccc2c3CCN=C(C)c3[nH]c2c1

assay

97%

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

mp

232-234 °C (lit.)

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Application

Reactant for preparation of:
  • Acylated harmalines via Friedel-Crafts reaction
  • Phenacyl derivatives of 1-methyl-7-methoxy-β-carbolines as central nervous system affectors
  • Palladium harmaline DMSO chloro complex as anti-tumor agent

Natural product scaffold in preparation of:
  • Trypanothione reductase inhibitors†

Biochem/physiol Actions

CNS stimulant; may act through NMDA receptors

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
28511MI
11009DQ
14004TR
04526DG
02519PU

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Danuše Tarkowská
Molecules (Basel, Switzerland), 25(14) (2020-07-28)
Many substances of secondary plant metabolism have often attracted the attention of scientists and the public because they have certain beneficial effects on human health, although the reason for their biosynthesis in the plant remains unclear. This is also the
Jenny Bain et al.
The Biochemical journal, 408(3), 297-315 (2007-09-14)
The specificities of 65 compounds reported to be relatively specific inhibitors of protein kinases have been profiled against a panel of 70-80 protein kinases. On the basis of this information, the effects of compounds that we have studied in cells
Jiawang Liu et al.
Journal of medicinal chemistry, 53(8), 3106-3116 (2010-03-25)
3S-Tetrahydro-beta-carboline-3-carboxylic acid (TCCA) effectively inhibits ADP-induced platelet activation. This paper used TCCA as a lead, modified its 2-position with amino acids, and provided 20 novel 3S-2-aminoacyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acids (5a-t). With the in vitro assay, it was demonstrated that this modification diminished
Betty C Galarreta et al.
Bioorganic & medicinal chemistry, 16(14), 6689-6695 (2008-06-19)
Twenty-three heterocyclic compounds were evaluated for their potential as trypanothione reductase inhibitors. As a result, the harmaline, 10-thiaisoalloxazine, and aspidospermine frameworks were identified as the basis of inhibitors of Trypanosoma cruzi trypanothione reductase. Two new compounds showed moderately strong, linear
Chunyu Li et al.
European journal of medicinal chemistry, 46(11), 5598-5608 (2011-10-11)
High anti-thrombotic activity of aminoacid modified tetrahydro-β-carbolines was generally correlated with a small proximity of the side chain of the aminoacid residue to the carboline-cycle. This paper explored that the aromatization of the tetrahydro-β-carboline-cycle of N-(1-methyl-β-tetrahydrocarboline-3-carbonyl)-N'-(aminoacid-acyl)-hydrazines leaded to N-(1-methyl-β-carboline-3-carbonyl)-N'-(aminoacid-acyl)-hydrazines and

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