Norharmane | CAS#244-63-3 | glucosidase inhibitor

MedKoo Cat#: 319605 | Name: Norharmane

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Norharmane is a β-Carboline alkaloid that is widespread in plants and animals, and frequently act as benzodiazepine inverse agonists. Norharmane showed a potent inhibition against α-glucosidase enzyme in a concentration dependent manner with an IC50 value of 0.27 mM for maltase and 0.41 mM for sucrase, respectively. A Lineweaver-Burk plot revealed that norharman inhibited α-glucosidase enzyme uncompetitively, with a Ki value of 0.13 mM.

Chemical Structure

Norharmane

CAS# 244-63-3 (Free base).

Theoretical Analysis

MedKoo Cat#: 319605

Name: Norharmane

CAS#: 244-63-3 (Free base).

Chemical Formula: C11H8N2

Exact Mass: 168.0687

Molecular Weight: 168.20

Elemental Analysis: C, 78.55; H, 4.79; N, 16.66

Price and Availability

Size	Price	Availability	Quantity
500mg	USD 150.00
1g	USD 250.00
2g	USD 450.00
5g	USD 850.00
10g	USD 1,550.00

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Related CAS #

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Synonym

Norharmane; β-Carboline; 2-Azacarbazole.

IUPAC/Chemical Name

9H-pyrido[3,4-b]indole

InChi Key

AIFRHYZBTHREPW-UHFFFAOYSA-N

InChi Code

InChI=1S/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H

SMILES Code

C(N1)(C=NC=C2)=C2C3=C1C=CC=C3

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Norharmane is a potent and reversible monoamine oxidase inhibitor, with IC50 values of 6.5 and 4.7 μM for MAO-A and MAO-B.

In vitro activity:

The present study evaluated the quorum sensing (QS) and biofilm inhibitory effects of seven carboline compounds against S. marcescens NJ01 at 20 μg ml-1, and subsequently focused the study on norharmane as this had the best inhibitory activity. Norharmane exposure also enhanced the susceptibility of the biofilm to ofloxacin. Reference: Biofouling. 2021 Feb;37(2):145-160. https://pubmed.ncbi.nlm.nih.gov/33682541/

In vivo activity:

The present study was designed to investigate the effect of norharmane (benzodiazepine receptor inverse agonist) and L-glutamic acid (glutamate receptor agonist) on brotizolam induced anterograde and retrograde amnesia using Morris water maze task in mice. Norharmane reversed anterograde amnesia induced by brotizolam and did not reverse retrograde amnesia induced by it. Reference: Behav Brain Res. 2007 Aug 22;182(1):12-20. https://pubmed.ncbi.nlm.nih.gov/17561282/

	Solvent	mg/mL	mM
Solubility
	DMF	1.0	5.95
	DMSO	15.3	91.16
	Ethanol	2.5	14.86

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 168.20 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Luo HZ, Zhou JW, Sun B, Jiang H, Tang S, Jia AQ. Inhibitory effect of norharmane on Serratia marcescens NJ01 quorum sensing-mediated virulence factors and biofilm formation. Biofouling. 2021 Feb;37(2):145-160. doi: 10.1080/08927014.2021.1874942. Epub 2021 Mar 7. PMID: 33682541. 2. Iwashita H, Sano M, Chiba A. Effects of endogenous and exogenous N-acetyl-5-methoxy kynuramine on object recognition memory in male C3H mice. Horm Behav. 2023 Apr;150:105329. doi: 10.1016/j.yhbeh.2023.105329. Epub 2023 Feb 24. PMID: 36841054. 3. Anand A, Saraf MK, Prabhakar S. Sustained inhibition of brotizolam induced anterograde amnesia by norharmane and retrograde amnesia by L-glutamic acid in mice. Behav Brain Res. 2007 Aug 22;182(1):12-20. doi: 10.1016/j.bbr.2007.04.022. Epub 2007 May 3. PMID: 17561282.

In vitro protocol:

In vivo protocol:

1. Iwashita H, Sano M, Chiba A. Effects of endogenous and exogenous N-acetyl-5-methoxy kynuramine on object recognition memory in male C3H mice. Horm Behav. 2023 Apr;150:105329. doi: 10.1016/j.yhbeh.2023.105329. Epub 2023 Feb 24. PMID: 36841054. 2. Anand A, Saraf MK, Prabhakar S. Sustained inhibition of brotizolam induced anterograde amnesia by norharmane and retrograde amnesia by L-glutamic acid in mice. Behav Brain Res. 2007 Aug 22;182(1):12-20. doi: 10.1016/j.bbr.2007.04.022. Epub 2007 May 3. PMID: 17561282.

1: Wojtowicz E, Zawirska-Wojtasiak R, Przygoński K, Mildner-Szkudlarz S. Bioactive β-carbolines norharman and harman in traditional and novel raw materials for chicory coffee. Food Chem. 2015 May 15;175:280-3. doi: 10.1016/j.foodchem.2014.11.143. Epub 2014 Nov 29. PubMed PMID: 25577081. 2: Wabaidur SM, Lee SH, Alothman ZA, Siddiqui MR, Alam SM. Second derivative synchronous fluorimetric method for simultaneous determination of harman and norharman in coffee samples. Spectrochim Acta A Mol Biomol Spectrosc. 2013 Jun;110:179-84. doi: 10.1016/j.saa.2013.03.045. Epub 2013 Mar 16. PubMed PMID: 23563636. 3: Esmaeili MH, Movahedi M, Faraji A, Haghdoost-Yazdi H. Intracerebral injection of low amounts of norharman induces moderate Parkinsonism-like behavioral symptoms in rat. Neurotoxicol Teratol. 2012 Sep-Oct;34(5):489-94. doi: 10.1016/j.ntt.2012.07.001. Epub 2012 Jul 9. PubMed PMID: 22789434. 4: Tan C, Wu S, Lai S, Wang M, Chen Y, Zhou L, Zhu Y, Lian W, Peng W, Ji L, Xu A. Synthesis, structures, cellular uptake and apoptosis-inducing properties of highly cytotoxic ruthenium-Norharman complexes. Dalton Trans. 2011 Sep 14;40(34):8611-21. doi: 10.1039/c1dt10084j. Epub 2011 Jul 29. PubMed PMID: 21804968. 5: Thatcher RJ, Douthwaite RE. β-Carboline (norharman). Acta Crystallogr C. 2011 Jul;67(Pt 7):o241-3. doi: 10.1107/S0108270111021706. Epub 2011 Jun 23. PubMed PMID: 21727633. 6: Haghdoost-Yazdi H, Hosseini SS, Faraji A, Nahid D, Jahanihashemi H. Long term exposure to norharman exacerbates 6-hydroxydopamine-induced parkinsonism: possible involvement of L-type Ca2+ channels. Behav Brain Res. 2010 Dec 20;215(1):136-40. doi: 10.1016/j.bbr.2010.07.011. Epub 2010 Jul 16. PubMed PMID: 20638417. 7: Herraiz T, Guillén H, Arán VJ. Oxidative metabolism of the bioactive and naturally occurring beta-carboline alkaloids, norharman and harman, by human cytochrome P450 enzymes. Chem Res Toxicol. 2008 Nov;21(11):2172-80. doi: 10.1021/tx8002565. PubMed PMID: 19238614. 8: Yang YJ, Lee JJ, Jin CM, Lim SC, Lee MK. Effects of harman and norharman on dopamine biosynthesis and L-DOPA-induced cytotoxicity in PC12 cells. Eur J Pharmacol. 2008 Jun 10;587(1-3):57-64. doi: 10.1016/j.ejphar.2008.03.050. Epub 2008 Apr 4. PubMed PMID: 18457825. 9: Alves RC, Casal S, Oliveira BP. Factors influencing the norharman and harman contents in espresso coffee. J Agric Food Chem. 2007 Mar 7;55(5):1832-8. Epub 2007 Feb 10. PubMed PMID: 17291006. 10: Ostergren A, Lindquist NG, Brittebo EB. Differential effects of dopamine melanin on norharman-induced toxicity in PC12 cells. J Neural Transm (Vienna). 2007 Jul;114(7):909-18. Epub 2007 Jan 28. PubMed PMID: 17256107. 11: Zheng L, Yan X, Han X, Chen H, Lin W, Lee FS, Wang X. Identification of norharman as the cytotoxic compound produced by the sponge (Hymeniacidon perleve)-associated marine bacterium Pseudoalteromonas piscicida and its apoptotic effect on cancer cells. Biotechnol Appl Biochem. 2006 Jun;44(Pt 3):135-42. PubMed PMID: 16579793. 12: Herraiz T, Chaparro C. Human monoamine oxidase enzyme inhibition by coffee and beta-carbolines norharman and harman isolated from coffee. Life Sci. 2006 Jan 18;78(8):795-802. Epub 2005 Aug 31. PubMed PMID: 16139309. 13: Ostergren A, Fredriksson A, Brittebo EB. Norharman-induced motoric impairment in mice: neurodegeneration and glial activation in substantia nigra. J Neural Transm (Vienna). 2006 Mar;113(3):313-29. Epub 2005 Aug 3. PubMed PMID: 16075188. 14: Miralles A, Esteban S, Sastre-Coll A, Moranta D, Asensio VJ, García-Sevilla JA. High-affinity binding of beta-carbolines to imidazoline I2B receptors and MAO-A in rat tissues: norharman blocks the effect of morphine withdrawal on DOPA/noradrenaline synthesis in the brain. Eur J Pharmacol. 2005 Aug 22;518(2-3):234-42. PubMed PMID: 16061219. 15: Ichihara T, Miyashita K, Kawabe M, Imaida K, Asamoto M, Ogiso T, Tamano S, Hirose M, Shirai T. Lack of combination hepatocarcinogenicity of harman, norharman and amitrole when given with NaNO2 in the rat. J Toxicol Sci. 2005 Feb;30(1):1-6. PubMed PMID: 15800397. 16: Herraiz T. Relative exposure to beta-carbolines norharman and harman from foods and tobacco smoke. Food Addit Contam. 2004 Nov;21(11):1041-50. PubMed PMID: 15764332. 17: Fekkes D, Bernard BF, Cappendijk SL. Norharman and alcohol-dependency in male Wistar rats. Eur Neuropsychopharmacol. 2004 Oct;14(5):361-6. PubMed PMID: 15336296. 18: Nishigaki R, Totsuka Y, Takamura-Enya T, Sugimura T, Wakabayashi K. Identification of cytochrome P-450s involved in the formation of APNH from norharman with aniline. Mutat Res. 2004 Aug 8;562(1-2):19-25. PubMed PMID: 15279827. 19: Kawamori T, Totsuka Y, Uchiya N, Kitamura T, Shibata H, Sugimura T, Wakabayashi K. Carcinogenicity of aminophenylnorharman, a possible novel endogenous mutagen, formed from norharman and aniline, in F344 rats. Carcinogenesis. 2004 Oct;25(10):1967-72. Epub 2004 May 13. PubMed PMID: 15142889. 20: Eggers V, Fügener K, Hein OV, Rommelspacher H, Heyes MP, Kox WJ, Spies CD. Antibiotic-mediated release of tumour necrosis factor alpha and norharman in patients with hospital-acquired pneumonia and septic encephalopathy. Intensive Care Med. 2004 Aug;30(8):1544-51. Epub 2004 Apr 27. PubMed PMID: 15112034.