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Usage

Uses

Used in Pharmaceutical Applications:
Harmane is utilized as a sedative and anxiolytic agent due to its psychoactive properties, which can help alleviate symptoms of anxiety and promote relaxation.
Used in Neurological Research:
In the field of neuroscience, harmane is studied for its potential role in the development and progression of neurological conditions such as Alzheimer's and Parkinson's disease. Its presence in the brain and its interactions with neurodegenerative processes make it a valuable subject for research.
Used as a Biomarker in Psychiatric Disorders:
Harmane's potential as a biomarker for certain psychiatric disorders is being explored, as its levels in the body may indicate the presence or severity of specific mental health conditions.
Used in Forensic Toxicology:
In forensic toxicology, harmane is of interest as it has been detected in post-mortem samples. Its presence may serve as an indicator of exposure to certain substances, aiding in the determination of cause of death or substance abuse history.
Used in Food and Plant Analysis:
As harmane is found in various plants and foods, it can be used for analysis to determine the presence and concentration of this alkaloid, which may have implications for dietary intake and potential health effects.

InChI:InChI=1/C12H12N2O2/c1-16-7-2-3-10-9(6-7)8-4-5-13-12(15)11(8)14-10/h2-3,6,14H,4-5H2,1H3,(H,13,15)

Upstream product

• 19501-58-7 4-methoxyphenylhydrazine hydrochloride 
• 608-07-1 2-(5-methoxyindol-3-yl)ethylamine 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 104-94-9 4-methoxy-aniline 
• 4346-59-2 para-methoxyphenyldiazonium chloride 
• 104742-98-5 2,3-dioxopiperidine 3-(p-methoxyphenyl)hydrazone 
• 108171-00-2 3-(4-methoxy-phenylazo)-2-oxo-piperidine-3-carboxylic acid ethyl ester 

Downstream Products

• 608-07-1 2-(5-methoxyindol-3-yl)ethylamine 
• 129300-83-0 9-(2-dibenzylaminoethyl)-6-methoxy-1-oxo-1,2,3,4-tetrahydro-β-carboline 
• 129280-69-9 9-(2-cyclohexylaminoethyl)-6-methoxy-1-oxo-1,2,3,4-tetrahydro-β-carboline 
• 129300-84-1 9-(2-dibenzylaminoethyl)-2-methyl-6-methoxy-1-oxo-1,2,3,4-tetrahydro-β-carboline 
• 1053644-75-9 (3aS,4S,6R,6aR)-6-(6-{2-[1-(2,5-Dimethyl-benzyl)-5-methoxy-1H-indol-3-yl]-ethylamino}-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid cyclopropylamide 
• 174727-69-6 2-[1-(2,5-Dimethyl-benzyl)-5-methoxy-1H-indol-3-yl]-ethylamine 
• 66-83-1 5-methoxytryptamine hydrochloride 
• 52648-13-2 5-methoxytryptamine-2-carboxylic acid 
• 20315-68-8 pinoline 

Relevant academic research and scientific papers

Fischer Reaction with 2-Perfluoroalkylated Cyclic Imines - An Efficient Route to 2-Perfluoroalkyl-Substituted Tryptamines and Their Derivatives and Homologues

The reaction of 2-perfluoroalkyl-substituted cyclic imines with arylhydrazines was investigated. We found that 2-perfluoroalkylated cyclic imines are highly reactive electrophiles that form, through ring opening, the corresponding hydrazones bearing an amine group at the end of the alkyl chain. Subsequent acidic treatment resulted in a Fischer rearrangement. Thus, a new synthesis of 2-perfluoroalkylated tryptamines and their homologues through a Fischer reaction was developed. The possibility of modification of the indole core of the 2-CF3-substituted tryptamine products was demonstrated, and various 2-trifluoromethylated tryptamines substituted at the 5-position were prepared. An efficient method for the synthesis of CF3-substituted tryptamines was developed based on the Fischer reaction of perfluoroalkyl-substituted cyclic imines with arylhydrazines. A 5-bromotryptamine was also transformed into further derivatives.

Synthesis of the carboline disaccharide domain of shishijimicin A

A synthetic route to the carboline disaccharide domain (2) of shishijimicin A (1) has been developed. The convergent synthesis relies on a novel application of the Reetz-Mueller-Starke reaction to form the central, sulfur-bearing quaternary carbon center

Syntheses of 7-fluoro- and 6,7-difluoroserotonin and 7-fluoro- and 6,7-difluoromelatonin

The Abramovitch adaption of the Fischer indole synthesis gave low yields of 7-fluoro-5-methoxytryptamine due in part to decomposition during the required decarboxylation step. Therefore, 7-fluoro- and 6,7-difluoro-5-methoxytryptamines were prepared by rea

Synthesis and cytotoxic activity of novel quinazolino-β-carboline-5- one derivatives

A novel series of quinazolino-β-carbolinone derivatives was synthesized and evaluated for their in vitro and in vivo anticancer activity. Many compounds have shown good in vitro activity in the range 1-8μM concentration. Three of the compounds were further tested in nude mice bearing HT-29 colon cancer xenografts.

N6-Substituted Adenosine Receptor Agonists. Synthesis and Pharmacological Activity as Potent Antinociceptive Agents

Novel N6-(indol-3-yl)alkyl derivatives of adenosine were synthesized.The adenosine receptor affinity and the antinociceptive activity of these compounds were assessed in binding studies and the phenylbenzoquinone-induced writhing test.Most of these analogues exhibited a potent analgesic activity without side effects.Among them, compound 3c (UP 202-32) bound to A1 (Ki = 110 nM) and A2 (Ki = 350 nM) adenosine receptors in a specific manner since it did not interact with many other receptors, especially opioid binding sites.The antinociceptive activity in the phenylbenzoquinone assay (ED50 = 3.3 mg/kg po) was antagonized by 8-cyclopentyltheophylline, suggesting that an adenosinergic mechanism underlies the analgesic activity observed with this compound.The data obtained with these new N6-substituted adenosine receptor agonists emphasize the interest of such compounds in the treatment of pain.

Electron Impact and Chemical Ionization Fragmentation of 5-Methoxytryptamine and Some 6-Methoxy-β-carbolines

Electron impact (EI) and chemical ionization (CI) mass spectra of 5-methoxytryptamine (5-MT) and seven 6-methoxy-β-carbolines have been recorded and interpreted.Proposed fragmentation pathways are depicted on the basis of spectra of deuterium labelled analogs of 5-MT, 6-methoxy-1,2,3,4-tetrahydro-β-carboline (6-MeO-THBC) and 6-Methoxy-1-methyl-1,2,3,4-tetrahydro-β-carboline (6-MeO-1-Me-THBC).In the EI mass spectrum of 5-MT, the base peak m/z 160 is formed by the expulsion of CH4N.The positive ion so formed is suggested to have a quinolinium structure.In chemical ionization with CH4 as the reaction gas, the most abundant ion is produced by cleavage of NH3.The ion m/z 173 yields the base peak in the EI mass spectrum of 6-MeO-THBC.This ion is formed by a retro Diels-Alder reaction, an important fragmentation pathway of 6-MeO-1-Me-THBC, too. 6-MeO-harmalan easily loses one hydrogen atom in EI fragmentation followed by methyl loss from the methoxy group, this latter process yielding the base peak, m/z 197 in the EI mass spectrum of 6-MeO-harman.M+1 is the base peak in the CI mass spectra of all 6-MeO-β-carbolines.