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51330

Sigma-Aldrich

Harmaline

≥95%

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
Beilstein:
207310
EC Number:
206-152-6
MDL number:
MFCD00004955
UNSPSC Code:
12352100
PubChem Substance ID:
57651320
NACRES:
NA.22

Assay

≥95%

form

powder

drug control

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

Gene Information

human ... ADRA1A(148) , ADRA1B(147) , ADRA2A(150) , ADRA2B(151) , ADRA2C(152) , ADRB1(153) , ADRB2(154) , CHRM1(1128) , CHRM2(1129) , CHRM3(1131) , CHRM4(1132) , CHRM5(1133) , DRD1(1812) , DRD5(1816) , HTR1A(3350) , HTR1B(3351) , HTR1D(3352) , HTR2C(3358) , HTR3A(3359) , HTR5A(3361) , HTR6(3362) , HTR7(3363) , SLC6A2(6530) , SLC6A4(6532) , SLC9A2(6549) , SLC9A5(6553)
rat ... Drd2(24318) , Drd3(29238) , Drd4(25432) , Htr2a(29595) , Maoa(29253) , Maob(25750) , Slc9a1(24782) , Slc9a3(24784)

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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

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

Certificates of Analysis (COA)

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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
Farhan A Khan et al.
European journal of pharmacology, 721(1-3), 391-394 (2013-05-28)
Peganum harmala (L) is a perennial plant which is native of eastern Iranian and west of India but also found in different regions of western USA. A number of β-carboline compounds with therapeutic importance and different pharmacological effects, are present
M Xing et al.
Letters in applied microbiology, 54(5), 475-482 (2012-03-08)
To investigate the antimicrobial efficacy of an alkaloid, harmaline alone and in combination with chlorhexidine digluconate (CHG) against clinical isolates of Staphylococcus aureus (S. aureus) grown in planktonic and biofilm cultures. Minimum inhibitory concentrations (MICs) and minimum bactericidal concentrations (MBCs) were
Hamid-Reza Adhami et al.
Phytotherapy research : PTR, 25(8), 1148-1152 (2011-02-03)
To find new herbal compounds with an acetylcholinesterase (AChE) inhibitory effect, this study focused on herbal drugs and resins which have been used in Iranian traditional medicine for the treatment of cognitive disorders. Forty drugs were selected from authoritative written
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
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