HARMAN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H10N2
Molecular Weight	182.2212
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=NC=CC2=C1NC3=C2C=CC=C3

InChI

InChIKey=PSFDQSOCUJVVGF-UHFFFAOYSA-N

InChI=1S/C12H10N2/c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12/h2-7,14H,1H3

HIDE SMILES / InChI

Molecular Formula	C12H10N2
Molecular Weight	182.2212
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Benzodiazepine receptors; peripheral & central 9 Target ID: CHEMBL2096683 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6255348	Binding Agent 1076
Monoamine oxidase A 52 Target ID: CHEMBL1951 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16139309	Inhibitor 8504

PubMed

Title	Date	PubMed
Monoamine oxidase inhibitors allow locomotor and rewarding responses to nicotine.	2006-08	16395299
Analysis of monoamine oxidase enzymatic activity by reversed-phase high performance liquid chromatography and inhibition by beta-carboline alkaloids occurring in foods and plants.	2006-07-07	16386263
Antidepressant-like effect of harmane and other beta-carbolines in the mouse forced swim test.	2006-07	16183262
Phytochemical and pharmacological study of roots and leaves of Guiera senegalensis J.F. Gmel (Combretaceae).	2006-06-30	16443341
Theoretical study of structure, pKa, lipophilicity, solubility, absorption, and polar surface area of some centrally acting antihypertensives.	2006-03-15	16263295
[Ageing free radicals and cellular stress].	2006-03	16527207
Autoradiographical distribution of imidazoline binding sites in monoamine oxidase A deficient mice.	2006-03	16476082
In vitro and ex vivo distribution of [3H]harmane, an endogenous beta-carboline, in rat brain.	2006-03	16242163
Effect of chlorine as substituent on the photochemistry and acid-base properties of beta-carboline alkaloids.	2006-02-01	16263305
Human monoamine oxidase enzyme inhibition by coffee and beta-carbolines norharman and harman isolated from coffee.	2006-01-18	16139309
Understanding the importance of selenium and selenoproteins in muscle function.	2006-01	16314926
Melatonin, immune function and aging.	2005-11-29	16316470
Comprehensive photochemistry and photophysics of land- and marine-based beta-carbolines employing time-resolved emission and flash transient spectroscopy.	2005-11-05	16268735
Harmane inhibits serotonergic dorsal raphe neurons in the rat.	2005-11	16133137
Investigation of the separation of heterocyclic aromatic amines by reversed phase ion-pair liquid chromatography coupled with tandem mass spectrometry: the role of ion pair reagents on LC-MS/MS sensitivity.	2005-10-25	15878313
Characterisation of imidazoline I2 binding sites in pig brain.	2005-09-05	16109401
Aging and gene expression in the primate brain.	2005-09	16048372
Blood harmane concentrations and dietary protein consumption in essential tremor.	2005-08-09	16087903
Photochemistry of the alkaloids eudistomin N (6-bromo-nor-harmane) and eudistomin O (8-bromo-nor-harmane) and other bromo-beta-carbolines.	2005-07-01	15963435
Fluorescence quenching of beta-carboline alkaloids in micellar media. A study to select the adequate surfactant to use in analytical techniques.	2005-06-01	15924317
Mitochondrial ageing of a polar and a temperate mud clam.	2005-05	15811430
Chronological and physiological ageing in a polar and a temperate mud clam.	2005-05	15811429
Lack of combination hepatocarcinogenicity of harman, norharman and amitrole when given with NaNO2 in the rat.	2005-02	15800397
Human monoamine oxidase is inhibited by tobacco smoke: beta-carboline alkaloids act as potent and reversible inhibitors.	2005-01-14	15582589
Estimate of illnesses from Salmonella enteritidis in eggs, United States, 2000.	2005-01	15705332
Modulation of voltage-gated channel currents by harmaline and harmane.	2005-01	15644868
Beta-carbolines induce apoptosis in cultured cerebellar granule neurons via the mitochondrial pathway.	2005-01	15617732
Matrix-assisted ultraviolet laser desorption/ionization time-of-flight mass spectrometry of beta-(1 --> 3), beta-(1 --> 4)-xylans from Nothogenia fastigiata using nor-harmane as matrix.	2005	15645484
Harmane and harmalan are bioactive components of classical clonidine-displacing substance.	2004-12-28	15610033
Relative exposure to beta-carbolines norharman and harman from foods and tobacco smoke.	2004-11	15764332
The putative imidazoline receptor agonist, harmane, promotes intracellular calcium mobilisation in pancreatic beta-cells.	2004-10-06	15464060
Evaluation of power prediction equations: peak vertical jumping power in women.	2004-09	15354042
Analysis of alpha- and beta-carbolines in mainstream smoke of reference cigarettes by gas chromatography-mass spectrometry.	2004-08-13	15387190
He's the dean of CEOs. Harman has held the top job at his West Virginia hospital for nearly 40 years--and counting.	2004-08-02	15332525
Modulation of cytochrome P450 1A1 by food-derived heterocyclic aromatic amines.	2004-07-01	15147796
Uncoupled and surviving: individual mice with high metabolism have greater mitochondrial uncoupling and live longer.	2004-06	15153176
Use of horseradish peroxidase for gene-directed enzyme prodrug therapy with paracetamol.	2004-05-04	15150627
Transport of harman alkaloids across Caco-2 cell monolayers.	2004-04	15056950
High-performance liquid chromatographic analysis of beta-carbolines in human scalp hair.	2004-03-26	15058601
Mutagens formed from beta-carbolines with aromatic amines.	2004-03-25	15036005
Exposure to beta-carbolines norharman and harman.	2004-03-25	15036003
Occurrence of heterocyclic amines in several home-cooked meat dishes of the Spanish diet.	2004-03-25	15035999
Atypical [(3)H]clonidine binding sites in human caudate and platelets on cryostat-cut sections.	2003-12	15028603
Endogenous imidazoline receptor ligands relax rat aorta by an endothelium-dependent mechanism.	2003-12	15028591
Harmane induces anxiolysis and antidepressant-like effects in rats.	2003-12	15028588
Effect of harmane on the convulsive threshold in epilepsy models in mice.	2003-12	15028587
Inhibitory effect of harmane on morphine-dependent Guinea pig ileum.	2003-12	15028586
Effect of harmane on mononeuropathic pain in rats.	2003-12	15028585
Characterization of [(3)H]harmane binding to rat whole brain membranes.	2003-12	15028584
In vitro activity of the beta-carboline alkaloids harmane, harmine, and harmaline toward parasites of the species Leishmania infantum.	2002-06-04	15172213

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:54:47 GMT 2025` Edited by `admin` on `Mon Mar 31 19:54:47 GMT 2025`
Record UNII	82D6J0535P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-54439

Preferred Name

English

HARMAN

Systematic Name

English

HARMAN [MI]

Common Name

English

9H-PYRIDO(3,4-B)INDOLE, 1-METHYL-

Systematic Name

English

Code System Code Type Description

ECHA (EC/EINECS)

207-642-2