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Merck

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

Key Documents

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InChI key

RERZNCLIYCABFS-UHFFFAOYSA-N

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

SMILES string

COc1ccc2c3CCN=C(C)c3[nH]c2c1

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.)

Quality Level

100

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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Related Categories

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

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
BCCL3882
BCCH6005
BCCC2186
BCBT9793
BCBP4993V

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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
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
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
Jordi Riba et al.
Drug testing and analysis, 4(7-8), 610-616 (2012-04-20)
Ayahuasca is an Amazonian psychotropic plant tea obtained from Banisteriopsis caapi, which contains β-carboline alkaloids, chiefly harmine, harmaline and tetrahydroharmine. The tea usually incorporates the leaves of Psychotria viridis or Diplopterys cabrerana, which are rich in N,N-dimethyltryptamine (DMT), a psychedelic
Hong-Wu Shen et al.
Current drug metabolism, 11(8), 659-666 (2010-10-15)
5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT) belongs to a group of naturally-occurring psychoactive indolealkylamine drugs. It acts as a nonselective serotonin (5-HT) agonist and causes many physiological and behavioral changes. 5-MeO-DMT is O-demethylated by polymorphic cytochrome P450 2D6 (CYP2D6) to an active metabolite, bufotenine
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