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343-27-1

343-27-1 Structure

343-27-1 Structure
IdentificationMore
[Name]

HARMINE HYDROCHLORIDE
[CAS]

343-27-1
[Synonyms]

7-METHOXY-1-METHYL-9H-PYRIDO[3,4-B]INDOLE HCL
7-METHOXY-1-METHYL-9H-PYRIDO[3,4-B]INDOLE HYDROCHLORIDE
BANISTERINE HYDROCHLORIDE
BANISTERIN HCL
HARMINE HCL
HARMINE HYDROCHLORIDE
4-b)indole,7-methoxy-1-methyl-9h-pyrido(monohydrochloride
harminemonohydrochloride
HARMINE HYDROCHLORIDE HYDRATE 98%
HARMINE HYDROCHLORID
CATHARANTHIN TARTRATE
DL-ANABASINE Hydrochloride
[EINECS(EC#)]

206-443-8
[Molecular Formula]

C13H13ClN2O
[MDL Number]

MFCD00012641
[Molecular Weight]

248.71
[MOL File]

343-27-1.mol
Chemical PropertiesBack Directory
[Appearance]

yellow to slightly green crystalline powder
[Melting point ]

265-270°C
[storage temp. ]

2-8°C
[solubility ]

Soluble in Water (up to 25 mg/ml).
[form ]

powder
[color ]

off-white to pale green
[Merck ]

4616
[Stability:]

Stable for 2 years from date of purchase as supplied. Solutions in distilled water may be stored at -20° for up to 3 months.
[Major Application]

metabolomics
vitamins, nutraceuticals, and natural products
[InChI]

1S/C13H12N2O.ClH/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13;/h3-7,15H,1-2H3;1H
[InChIKey]

VNPLYCKZIUTKJM-UHFFFAOYSA-N
[SMILES]

Cl.COc1ccc2c(c1)[nH]c3c(C)nccc23
[LogP]

3.173 (est)
[CAS DataBase Reference]

343-27-1(CAS DataBase Reference)
[EPA Substance Registry System]

Harmine hydrochloride (343-27-1)
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R40:Limited evidence of a carcinogenic effect.
[Safety Statements ]

S22:Do not breathe dust .
S36:Wear suitable protective clothing .
[RIDADR ]

1544
[WGK Germany ]

3
[RTECS ]

MG9450000
[HazardClass ]

6.1(b)
[PackingGroup ]

III
[HS Code ]

29339900
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Acute Tox. 4 Oral
Carc. 2
Hazard InformationBack Directory
[Description]

Harmine (343-27-1) is a selective competitive and reversible inhibitor of MAO-A (IC50?= 8 μM).1?Harmine is a potent and specific inhibitor of both the kinase activity and autophosphorylation of tyrosine during translation DYRK1A (IC50‘s: DYRKA1A = 33 nM; DYRKA1B = 166 nM; DYRK2 = 1.9 μM; DYRK4 = 80 μM).2,3?Inhibits self-renewal and promotes differentiation of glioblastoma stem-like cells (GSLC’s) possibly via inhibition of Akt phosphorylation.4?Harmine has also been shown to possess antimicrobial, antifungal, antiplasmodial, antitumor, antioxidant, antimutagenic and antigenotoxic properties.5?Inhibits osteoclast differentiation and bone resorption via downregulation of c-Fos and NFATc1 induced by RANKL.6
[Chemical Properties]

yellow to slightly green crystalline powder
[Uses]

Harmine Monohydrochloride is an anti-viral agents for the treatment of EV71 infection. It inhibits enterovirus 71 replication by targeting NF-κB pathway.
[in vivo]

It is shown that brain water content is significantly increased in the TBI group. Treatment with Harmine significantly reduces the tissue water content at 1, 3 and 5 days, compared with the TBI group. Harmine treatment significantly reduces the escape latency at 3 and 5 days, compared with the TBI group. Post-TBI administration of Harmine significantly improves the motor function recovery of the rats at 1, 3 and 5 days following TBI, compared with the TBI group without Harmine treatment. The neuronal survival rate in the Harmine-treated group is significantly increased, compared with the TBI group. Administration of Harmine results in marked elevation in the expression of GLT-1, compared with the TBI group. The administration of Harmine significantly reduces the expression of caspase 3, compared with the TBI group[4].

[IC 50]

5-HT2A Receptor: 397 nM (Ki); DYRK1A
[Purification Methods]

The hydrate crystallises as fluorescent crystals from water. The anhydrous salt has m 319o. [Beilstein 23/12 V 237.]
[References]

1) Wouters (1998)?Structural Aspects of Monoamine Oxidase and its Reversible Inhibition?Current Medicinal Chemistry,?5?137 2) Seifert?et al. (2008)?DYRK1A phosphorylates caspase 9 at an inhibitory site and is potently inhibited in human cells by harmine; FEBS J.,?275?6268 3) Gockler?et al. (2009)?Harmine specifically inhibits protein kinase DYRK1A and interferes with neurite outgrowth; FEBS J.,?276?6324 4) Liu?et al. (2013)?Harmine hydrochloride inhibits Akt phosphorylation and depletes the pool of cancer stem-like cells of glioblastoma; J .Neurooncol.,?112?39 5) Patel?et al. (2012)?A review on medical importance, pharmacological activity and bioanalytical aspects of beta-carboline alkaloid ‘Harmine’; Asian Pac. J. Trop. Biomed.,?2?660 6) Yoneazwa?et al. (2011)?Harmine, a β-carboline alkaloid, inhibits osteoclast differentiation and bone resorption in vitro and in vivo; Eur. J. Pharmacol.,?650?511
Spectrum DetailBack Directory
[Spectrum Detail]

HARMINE HYDROCHLORIDE(343-27-1)1HNMR
HARMINE HYDROCHLORIDE(343-27-1)IR1
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

343-27-1(sigmaaldrich)
[TCI AMERICA]

Harmine Hydrochloride,>98.0%(LC)(T)(343-27-1)
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