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51330

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
57651320
EC Number:
206-152-6
Beilstein/REAXYS Number:
207310
MDL number:
MFCD00004955
Assay:
≥95%
Form:
powder
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Quality Level

100

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)

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

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pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

hcodes

H302,H371

Hazard Classifications

Acute Tox. 4 Oral - STOT SE 2

target_organs

Central nervous system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
1401557
1379442
1343491
290008/1
1240906

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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
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Global Trade Item Number

SKUGTIN
51330-1G04061832492520