486-84-0 Usage
Description
Harmane, also known as β-carboline alkaloid, is a potent tremor-producing neurotoxin and a major representative of heterocyclic aromatic amines. It is formed in meat from precursors such as creatine, creatinine, amino acids, and sugars during high-temperature heating. Harmane has been isolated from various plant sources and is a specific, reversible inhibitor of monoamine oxidase A. It is an off-white solid and has been linked to elevated blood concentration in essential tremor and late-life neurological diseases.
Uses
Used in Trace Level Determination:
Harmane is used as a trace level determinant by planar chromatography coupled with tandem mass spectrometry for its analysis.
Used in DNA Interaction Studies:
Harmane is utilized in studying the interactions of norharman and harman with DNA, which can provide insights into its biological effects and potential applications.
Used in Analysis of Cyclodextrins:
Harmane serves as a matrix for the analysis of cyclodextrins, which are important in various chemical and pharmaceutical applications.
Used in Sulfated Oligosaccharides Analysis:
In combination with DHB as a co-matrix, harmane is used for the analysis of sulfated oligosaccharides, which have potential applications in the development of new drugs and therapies.
Used in Pharmaceutical Industry:
Harmane, due to its inhibitory effects on monoamine oxidase A, can be explored for its potential use in the development of pharmaceuticals targeting neurological disorders and other conditions related to monoamine oxidase A activity.
Used in Toxicology and Environmental Studies:
As a potent neurotoxin and a member of heterocyclic aromatic amines, harmane can be studied in toxicology and environmental research to understand its effects on human health and the environment, as well as to develop methods for its detection and mitigation.
Synthesis Reference(s)
The Journal of Organic Chemistry, 37, p. 1429, 1972 DOI: 10.1021/jo00974a030Tetrahedron, 49, p. 3325, 1993 DOI: 10.1016/S0040-4020(01)90161-9
Biological Activity
Proposed as the endogenous ligand for imidazoline binding sites. Binds to I 1 -sites in rat kidney with an IC 50 of 31 nM, and I 2 -sites with a K i of 49 nM. In vivo, produces a dose-dependent hypotension that is reversed by efaroxan (2-(2-Ethyl-2,3-dihydro-2-benzofuranyl)-4,5-dihydro-1H-imidazole hydrochloride ). Also a potent inhibitor of monoamine oxidases A and B (I 50 values are 0.5 and 5 μ M respectively).
Biochem/physiol Actions
I1 imidazoline binding site agonist.
Check Digit Verification of cas no
The CAS Registry Mumber 486-84-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,8 and 6 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 486-84:
(5*4)+(4*8)+(3*6)+(2*8)+(1*4)=90
90 % 10 = 0
So 486-84-0 is a valid CAS Registry Number.
InChI:InChI=1/C12H10N2/c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12/h2-7,14H,1H3
486-84-0Relevant articles and documents
Indole alkaloids from two species of Ophiorrhiza
Dachriyanus,Arbain, Dayar,Putra, Deddi Prima,Sargent, Melvyn V.,Susila, Revi,Wahyuni, Fatma Sri
, p. 221 - 224 (2000)
Extraction of the aerial parts of Ophiorrhiza rosacea Ridley (Rubiaceae) has yielded harman-2-oxide (1). Extraction of the aerial parts of O. kunstleri King yielded the alkaloids palicoside (3) and 3,14-didehydro-19-methylnormalindine (8). The structures
A new method for the synthesis of the marine alkaloid fascaplysin based on the microwave-assisted Minisci reaction
Zhidkov, Maxim E.,Kaminskii, Vladimir A.
, p. 3530 - 3532 (2013)
A new two-step method for the synthesis of the marine alkaloid fascaplysin has been developed, via homolytic benzoylation (Minisci reaction) of β-carboline under microwave irradiation followed by intermolecular quaternization.
A convenient synthesis of β-carbolines by iron-catalyzed aerobic decarboxylative/dehydrogenative aromatization of tetrahydro-β-carbolines under air
Mohamad Arshad, Ahmad Saifuddin,Meesala, Ramu,Hanapi, Nur Aziah,Mordi, Mohd Nizam
, (2021/02/12)
A convenient synthesis for the conversion of various substituted tetrahydro-β-carbolines has been developed by iron-catalyzed decarboxylative/dehydrogenative aromatization to construct aromatic β-carbolines under air atmosphere. In the presence of a FeCl3 catalyst, this reaction exhibited a good functional group tolerance to produce corresponding β-carbolines in good yields in the absence of any additive. Additionally, the utility of the method was highlighted in the gram-scale synthesis of important natural β-carboline synthons norharmane (2a) and harmane (2b), which the latter provide practical access towards eudistomin N and nostocarboline.
Application of metal free aromatization to total synthesis of perlolyrin, flazin, eudistomin U and harmane
Santhanam, Srinath,Ramu, Abinaya,Baburaj, Baskar,Kalpatu Kuppusamy, Balasubramanian
, p. 2121 - 2127 (2020/03/04)
Application of our recently reported metal free reaction conditions to the total synthesis of the four different and selective biologically interesting β-carboline natural products is reported. Using this simple methodology, flazin, perlolyrine, eudistomin U and harmane containing heteroaryl and alkyl substituents at C1 position were synthesized in good yields. (Figure presented.).