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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/REAXYS Number:
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

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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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
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
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
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
Monkeys with nigrostriatal lesions: tremor induced by harmaline and other drugs.
L J Poirier et al.
Pharmacology & therapeutics. Part B: General & systematic pharmacology, 2(1), 105-122 (1976-01-01)
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