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51330

Sigma-Aldrich

Harmaline

≥95%

Sinonimo/i:

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

Formula empirica (notazione di Hill):
C13H14N2O
Numero CAS:
304-21-2
Peso molecolare:
214.26
Beilstein:
207310
Numero CE:
206-152-6
Numero MDL:
MFCD00004955
Codice UNSPSC:
12352100
ID PubChem:
57651320
NACRES:
NA.22

Livello qualitativo

100

Saggio

≥95%

Stato

powder

Controllo stupefacenti

regulated under CDSA - not available from Sigma-Aldrich Canada

drug control

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

Punto di fusione

232-234 °C (lit.)

Stringa SMILE

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
RERZNCLIYCABFS-UHFFFAOYSA-N

Informazioni sul gene

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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Applicazioni

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†

Azioni biochim/fisiol

CNS stimulant; may act through NMDA receptors

Pittogrammi

Health hazardExclamation mark
GHS08,GHS07

Avvertenze

Warning

Indicazioni di pericolo

H302,H371

Classi di pericolo

Acute Tox. 4 Oral - STOT SE 2

Organi bersaglio

Central nervous system

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

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Certificati d'analisi (COA)

Lot/Batch Number
BCCC2186
BCBT9793
BCBP4993V
BCBK5380V
BCBH7580V

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Sigma-Aldrich

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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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