Norharmane

• CAT Number: I008328
• CAS Number: 244-63-3
• Molecular Formula: C11H8N2
• Molecular Weight: 168.19
• Purity: 98%
• Synonyms: Norharmane; β-Carboline; 2-Azacarbazole.;9H-pyrido[3,4-b]indole
• Target: Metabolic Enzyme/Protease
• Solubility: Soluble in DMSO, not in water
• Appearance: Solid powder
• Storage: Room Temperature
• IUPAC Name: 9H-pyrido[3,4-b]indole
• InChI: InChI=1S/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H
• InChIKey: AIFRHYZBTHREPW-UHFFFAOYSA-N
• SMILES: C1=CC=C2C(=C1)C3=C(N2)C=NC=C3

Norharmane（Cat No.:I008328）, is a naturally occurring compound found in coffee. It exhibits potent and selective inhibitory activity against monoamine oxidase A (MAO-A), an enzyme responsible for the breakdown of neurotransmitters such as serotonin, norepinephrine, and dopamine. By inhibiting MAO-A, Norharmane can increase the levels of these neurotransmitters, potentially influencing mood and behavior. With a Ki value of 3.34 μM, Norharmane shows a strong affinity for MAO-A, highlighting its potential as a therapeutic agent for conditions associated with imbalances in neurotransmitter levels.

Reference

1:Norharmane Matrix Enhances Detection of Endotoxin by MALDI-MS for Simultaneous Profiling of Pathogen, Host, and Vector Systems. Scott AJ, Flinders B, Cappell J, Liang T, Pelc RS, Tran B, Kilgour DP, Heeren RM, Goodlett DR, Ernst RK.Pathog Dis. 2016 Sep 19. pii: ftw097. [Epub ahead of print] PMID: 27650574
2:Transition-metal norharmane compounds as possible cytotoxic agents: New insights based on a coordination chemistry perspective. Khan RA, de Almeida A, Al-Farhan K, Alsalme A, Casini A, Ghazzali M, Reedijk J.J Inorg Biochem. 2016 Dec;165:128-135. doi: 10.1016/j.jinorgbio.2016.07.001. Epub 2016 Jul 7. PMID: 27453532
3:Contrasting Effects of Salt and Temperature on Niosome-Bound Norharmane: Direct Evidence for Positive Heat Capacity Change in the Niosome:β-Cyclodextrin Interaction. Paul BK, Ghosh N, Mondal R, Mukherjee S.J Phys Chem B. 2016 May 5;120(17):4091-101. doi: 10.1021/acs.jpcb.6b02168. Epub 2016 Apr 27. PMID: 27082934
4:Norharmane rhenium(I) polypyridyl complexes: synthesis, structural and spectroscopic characterization. Maisuls I, Wolcan E, Piro OE, Etcheverría GA, Petroselli G, Erra-Ballsels R, Cabrerizo FM, Ruiz GT.Dalton Trans. 2015 Oct 21;44(39):17064-74. doi: 10.1039/c5dt02790j. Epub 2015 Sep 14. PMID: 26365709
5:PhI(OAc)2-mediated one-pot oxidative decarboxylation and aromatization of tetrahydro-β-carbolines: synthesis of norharmane, harmane, eudistomin U and eudistomin I. Kamal A, Tangella Y, Manasa KL, Sathish M, Srinivasulu V, Chetna J, Alarifi A.Org Biomol Chem. 2015 Aug 28;13(32):8652-62. doi: 10.1039/c5ob00871a. Epub 2015 Jun 22. PMID: 26099113
6:Effects of adolescent treatment with nicotine, harmane, or norharmane in male Sprague-Dawley rats. Goodwin AK, Lantz-McPeak SM, Robinson BL, Law CD, Ali SF, Ferguson SA.Neurotoxicol Teratol. 2015 Jan-Feb;47:25-35. doi: 10.1016/j.ntt.2014.10.005. Epub 2014 Oct 31. PMID: 25450662
7:Prototropic transformation and rotational-relaxation dynamics of a biological photosensitizer norharmane inside nonionic micellar aggregates. Paul BK, Ghosh N, Mukherjee S.J Phys Chem B. 2014 Sep 25;118(38):11209-19. doi: 10.1021/jp5056717. Epub 2014 Sep 12. PMID: 25178117
8:Light-stable bis(norharmane)silver(I) compounds: synthesis, characterization and antiproliferative effects in cancer cells. Ahmad Khan R, Al-Farhan K, de Almeida A, Alsalme A, Casini A, Ghazzali M, Reedijk J.J Inorg Biochem. 2014 Nov;140:1-5. doi: 10.1016/j.jinorgbio.2014.06.019. Epub 2014 Jul 8. PMID: 25042730
9:Reinforcing and neural activating effects of norharmane, a non-nicotine tobacco constituent, alone and in combination with nicotine. Arnold MM, Loughlin SE, Belluzzi JD, Leslie FM.Neuropharmacology. 2014 Oct;85:293-304. doi: 10.1016/j.neuropharm.2014.05.035. Epub 2014 Jun 5. PMID: 24907588
10:Stepwise unfolding of bovine and human serum albumin by an anionic surfactant: an investigation using the proton transfer probe norharmane. Ghosh S, Chakrabarty S, Bhowmik D, Kumar GS, Chattopadhyay N.J Phys Chem B. 2015 Feb 12;119(6):2090-102. doi: 10.1021/jp501150p. Epub 2014 Apr 11. PMID: 24673409