Skip to Content
Merck
CN

H2256

Sigma-Aldrich

Harmaline

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

Sign Into View Organizational & Contract Pricing

About This Item

Empirical Formula (Hill Notation):
C13H14N2O
CAS Number:
304-21-2
Molecular Weight:
214.26
Beilstein:
207310
EC Number:
206-152-6
MDL number:
MFCD00004955
UNSPSC Code:
12352200
PubChem Substance ID:
329815185

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

drug control

stupéfiant (France); regulated under CDSA - not available from Sigma-Aldrich Canada
stupéfiant (France); regulated under CDSA - not available from Sigma-Aldrich Canada

mp

232-234 °C (lit.)

SMILES string

COc1ccc2c3CCN=C(C)c3[nH]c2c1

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

Looking for similar products? Visit Product Comparison Guide

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

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H302,H371

Hazard Classifications

Acute Tox. 4 Oral - STOT SE 2

Target Organs

Central nervous system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

新产品

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
057F0838
047H0638
028H0537
078F0116

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

W Du et al.
Brain research, 770(1-2), 26-29 (1998-01-24)
Harmaline, a beta-carboline derivative, is known to produce tremor through a direct activation of cells in the inferior olive. However, the receptor(s) through which harmaline acts remains unknown. It was recently reported that the tremorogenic actions of harmaline could be
Pervin K Iseri et al.
Neuropharmacology, 61(4), 715-723 (2011-06-07)
Essential tremor (ET) is one of the most common and most disabling movement disorders among adults. The drug treatment of ET remains unsatisfactory. Additional therapies are required for patients with inadequate response or intolerable side effects. The current study aims
Muhammad Rizwan-ul-Haq et al.
Chemosphere, 85(6), 995-1001 (2011-07-26)
Apolipophorin III, traditionally known for lipid transport in insects is fairly established as toxicity indicator against harmaline and tea saponin during this study. Apolipophorin III expressed in the hemolymph and midgut tissues of 3rd, 4th, 5th larval instars and pupae
Fatta B Nahab et al.
Neurotherapeutics : the journal of the American Society for Experimental NeuroTherapeutics, 9(3), 635-638 (2012-03-29)
Recent work exploring the use of high-molecular weight alcohols to treat essential tremor (ET) has identified octanoic acid as a potential novel tremor-suppressing agent. We used an established harmaline-based mouse model of ET to compare tremor suppression by 1-octanol and
Christine A Strick et al.
Neuropharmacology, 61(5-6), 1001-1015 (2011-07-19)
Observations that N-Methyl-D-Aspartate (NMDA) antagonists produce symptoms in humans that are similar to those seen in schizophrenia have led to the current hypothesis that schizophrenia might result from NMDA receptor hypofunction. Inhibition of D-amino acid oxidase (DAAO), the enzyme responsible
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service