Harmane

Harmane
Names

IUPAC name 1-Methyl-9H-pyrido[3,4-b]indole
Other names Harman, Aribine, Aribin, Locuturine, Locuturin, Loturine, Passiflorin, 1-Methylnorharman, NSC 54439
Identifiers
CAS Number	486-84-0
3D model (Jmol)	Interactive image
ChEBI	CHEBI:5623
ChemSpider	4444755
EC Number	207-642-2
KEGG	C09209
PubChem	5281404
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 Key: PSFDQSOCUJVVGF-UHFFFAOYSA-N InChI=1/C12H10N2/c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12/h2-7,14H,1H3 Key: PSFDQSOCUJVVGF-UHFFFAOYAA
SMILES CC1=NC=CC2=C1NC3=CC=CC=C23
Properties
Chemical formula	C₁₂H₁₀N₂
Molar mass	182.22
Melting point	235-238 °C(lit.)
Solubility in water	Soluble to 10 mM in 1eq. HCl^[1] methanol: soluble 50 mg/ml
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Harmane (harman) is a bio-active β-Carboline and monoamine oxidase inhibitor found in coffee^[2] and tobacco smoke.^[3] Harmane is strongly associated with Essential Tremor, one of the most common neurological diseases in the elderly.^[4] It is likely to be the main endogenous ligand for the benzodiazepine receptor. ^[5] Highest concentrations are found in cooked meat (chicken, beef, pork and fish).

References

↑ http://www.tocris.com/dispprod.php?ItemId=2101#.Ve7xsdc56fA
↑ 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.
↑ Human monoamine oxidase is inhibited by tobacco smoke: β-carboline alkaloids act as potent and reversible inhibitors Biochemical and Biophysical Research Communications Volume 326, Issue 2, 14 January 2005, Pages 378–386.
↑ Elevation of blood beta-carboline alkaloids in essential tremor http://web.ics.purdue.edu/~wzheng/Publications/Epapers/2002_Louis%20et%20al%20Neurology.pdf
↑ 1-Methyl-beta-carboline (harmane), a potent endogenous inhibitor of benzodiazepine receptor binding Naunyn Schmiedebergs Arch. Pharmacol. 1980 Oct;314(1):97-100

External links

Monoamine metabolism modulators

Common
(non-specific)

AAAD

MAO

Inhibitors: Non-selective: Benmoxin Caroxazone Echinopsidine Furazolidone Guineesine Hydralazine Indantadol Iproclozide Iproniazid Isocarboxazid Isoniazid Linezolid Mebanazine Metfendrazine Nialamide Octamoxin Paraxazone Phenelzine Pheniprazine Phenoxypropazine Pivhydrazine Procarbazine Safrazine Tranylcypromine

Inhibitors: MAO-A-selective: Amiflamine Bazinaprine Befloxatone Brofaromine Cimoxatone Clorgiline CX157 (Tyrima) Eprobemide Esuprone Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine) Methylene blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine Tetrindole Toloxatone

Inhibitors: MAO-B selective: Almoxatone D-Deprenyl Ethanol Ladostigil Lazabemide Milacemide Mofegiline Nicotine Pargyline^‡ Rasagiline Safinamide Selegiline (L-Deprenyl)

Phenethylamines
(dopamine, epinephrine,
norepinephrine)

PAH	Inhibitors: 3,4-Dihydroxystyrene

TH	Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Iodotyrosine Aquayamycin Bulbocapnine Metirosine Oudenone

DBH	Inhibitors: Bupicomide Disulfiram Dopastin Fusaric acid Nepicastat Phenopicolinic acid Tropolone

PNMT	Inhibitors: CGS-19281A SKF-64139 SKF-7698

COMT	Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone Entacapone Nitecapone Tolcapone

Tryptamines
(serotonin, melatonin)

TPH	Inhibitors: AGN-2979 Fenclonine (PCPA) Telotristat

See also: Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake and release modulators • Monoamine neurotoxins

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