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Harmane

CAT: 0804-HY-101392-02Size: 100 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-101392-02Size:100 mg
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Description
Harmane is a benzodiazepine receptor inhibitor (IC50=7 μM), with IC50 values for mACh, Opioid Receptor, MAO-A/B, and α2-adrenergic receptor of 24 μM, 2.8 μM, 0.5 μM, 5 μM, and 18 μM, respectively. Harmane inhibits the I1 imidazoline receptor (IC50 = 30 nM) to reduce blood pressure and has antidepressant, anti-anxiety, anticonvulsant, and analgesic effects. Harmane inhibits dopamine biosynthesis by decreasing tyrosine hydroxylase (TH) activity and enhancing L-DOPA-induced cytotoxicity in PC12 cells. Additionally, Harmane can increase the mutagenic effect induced by 2-acetylaminofluorene (AAF) [1][2][3][4][5][6].
CAS Number
486-84-0
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Adrenergic Receptor; GABA Receptor; Imidazoline Receptor; Monoamine Oxidase; nAChR; Opioid Receptor
Type
Natural Products
Related Pathways
GPCR/G Protein; Membrane Transporter/Ion Channel; Neuronal Signaling
Applications
Cancer-programmed cell death
Field of Research
Inflammation/Immunology; Neurological Disease
Assay Protocol
https://www.medchemexpress.com/harmane.html
Purity
99.91
Solubility
DMSO : 100 mg/mL (ultrasonic) |H2O : < 0.1 mg/mL (ultrasonic; warming; heat to 60°C)
Smiles
CC1=NC=CC2=C1NC3=C2C=CC=C3
Molecular Formula
C12H10N2
Molecular Weight
182.23
Precautions
H302, H315, H319, H335
References & Citations
[1]Musgrave IF, et, al. Harmane produces hypotension following microinjection into the RVLM: possible role of I (1) -imidazoline receptors. Br J Pharmacol. 2000 Mar;129 (6) :1057-9.|[2]Glover V, et, al. β-Carbolines as selective monoamine oxidase inhibitors:In vivo implications|[3]Umezawa K, et, al. Comutagenic effect of norharman and harman with 2-acetylaminofluorene derivatives. Proc Natl Acad Sci U S A. 1978 Feb;75 (2) :928-30.|[4]W E Müller, et al. On the neuropharmacology of harmane and other beta-carbolines. Pharmacol Biochem Behav. 1981 May;14 (5) :693-9.|[5]E D Louis, et al. Harmane induces anxiolysis and antidepressant-like effects in rats. Ann N Y Acad Sci. 2005 Aug 9;65 (3) :391-6.|[6]Yoo Jung Yang, et al. 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.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
MAO-A; MAO-B; α adrenergic receptor

Chemical Information

Harman

Harman is an indole alkaloid fundamental parent with a structure of 9H-beta-carboline carrying a methyl substituent at C-1. It has been isolated from the bark of Sickingia rubra, Symplocus racemosa, Passiflora incarnata, Peganum harmala, Banisteriopsis caapi and Tribulus terrestris, as well as from tobacco smoke. It is a specific, reversible inhibitor of monoamine oxidase A. It has a role as an EC 1.4.3.4 (monoamine oxidase) inhibitor, an anti-HIV agent and a plant metabolite. It is an indole alkaloid fundamental parent, an indole alkaloid and a harmala alkaloid.

CAS Number486-84-0
PubChem CID5281404
IUPAC Name1-methyl-9H-pyrido[3,4-b]indole
Molecular FormulaC12H10N2
Molecular Weight182.22
XLogP3.6
Topological Polar Surface Area28.7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Heavy Atom Count14
Formal Charge0
Complexity216
SMILES
CC1=NC=CC2=C1NC3=CC=CC=C23
InChI
InChI=1S/C12H10N2/c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12/h2-7,14H,1H3
InChIKey
PSFDQSOCUJVVGF-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Harman
CAS: 486-84-0
CID: 5281404
Formula: C12H10N2
MW: 182.22
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight182.22
XLogP33.6
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Exact Mass182.084398327
Monoisotopic Mass182.084398327
Topological Polar Surface Area28.7 Ų
Heavy Atom Count14
Formal Charge0
Complexity216
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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