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HARMINE HYDROCHLORIDE

Product NameHARMINE HYDROCHLORIDE
CAS343-27-1
MFC13H13ClN2O
MW248.71
EINECS206-443-8
MOL File343-27-1.mol

Chemical Properties

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	14,4616
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 Information

Hazard Codes	Xn
Risk Statements	20/21/22-40
Safety Statements	22-36
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

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Description

Harmine (343-27-1) is a selective competitive and reversible inhibitor of MAO-A (IC50= 8 μM).1Harmine 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).2,3Inhibits self-renewal and promotes differentiation of glioblastoma stem-like cells (GSLC’s) possibly via inhibition of Akt phosphorylation.4Harmine has also been shown to possess antimicrobial, antifungal, antiplasmodial, antitumor, antioxidant, antimutagenic and antigenotoxic properties.5Inhibits 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-HT_2A 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 J. Structural aspects of monoamine oxidase and its reversible inhibition.[J]. Current medicinal chemistry, 1998, 5 2: 137-162.
[2] ANNE SEIFERT Paul R C Lindsey A Allan. DYRK1A phosphorylates caspase 9 at an inhibitory site and is potently inhibited in human cells by harmine[J]. The FEBS journal, 2008, 275 24: 6268-6280. DOI:10.1111/j.1742-4658.2008.06751.x
[3] NORA GÖCKLER. Harmine specifically inhibits protein kinase DYRK1A and interferes with neurite formation[J]. The FEBS journal, 2009, 276 21: 6324-6337. DOI:10.1111/j.1742-4658.2009.07346.x
[4] HUAILEI LIU. Harmine hydrochloride inhibits Akt phosphorylation and depletes the pool of cancer stem-like cells of glioblastoma.[J]. Journal of Neuro-Oncology, 2013, 112 1: 39-48. DOI:10.1007/s11060-012-1034-x
[5] K PATEL . A review on medicinal importance, pharmacological activity and bioanalytical aspects of beta-carboline alkaloid “Harmine”[J]. Asian Pacific journal of tropical biomedicine, 2012, 2 8: Pages 660-664. DOI:10.1016/s2221-1691(12)60116-6
[6] TAKAYUKI YONEZAWA . Harmine, a β-carboline alkaloid, inhibits osteoclast differentiation and bone resorption in vitro and in vivo[J]. European journal of pharmacology, 2011, 650 2: Pages 511-518. DOI:10.1016/j.ejphar.2010.10.048

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