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A CNS stimulant isolated from seeds of Peganum harmala L. Zygophyllaceae

antiparkinsonian, CNS stimulant

central nervous system stimulant

ChEBI: A harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7.

harmine, also known as telepathine, is an alkaloid of the β-carboline family that regulates pparγ expression through inhibition of the wnt signaling pathway. it also selectively binds to mao-a and reversibly inhibits monoamine oxidase a (mao-a) but not the variant mao-b[3].harmine has a severe cytotoxicity in hepatoma cells and holds great promise as an oncologic drug for anticancer treatment[4].[1] smith b, medda f, gokhale v, et al. recent advances in thedesign, synthesis, and biologicalevaluation of selective dyrk1a inhibitors: a new avenue for a diseasemodifying treatment of alzheimer’s?[j]. acs chemical neuroscience, 2012, 3(11):857-72.[2] waki h, park k w, mitro n, et al. the small molecule harmine is an antidiabetic cell-type-specific regulator of ppargamma expression.[j]. cell metabolism, 2007, 5(5):357-370.[3] ginovart n, meyer j h, boovariwala a, et al. positron emission tomography quantification of |[lsqb]|11c|[rsqb]|-harmine binding to monoamine oxidase-a in the human brain[j]. journal of cerebral blood flow & metabolism official journal of the international society of cerebral blood flow & metabolism, 2006, 26(3):330-44.[4] zhang l, zhang f, zhang w, et al. harmine suppresses homologous recombination repair and inhibits proliferation of hepatoma cells[j]. cancer biology & therapy, 2015, 16(11):1585-1592.

General procedure for the synthesis of 7-methoxy-1-methyl-9H-pyrido[3,4-b]indole from camptothecin standard 002: 5 mmol of 6-methoxytryptamine was placed in a 100 mL round-bottomed flask, 50 mL of an aqueous solution containing 1 mL of concentrated hydrochloric acid was added, and the reaction was stirred at 30 °C until complete dissolution. Subsequently, 10 mmol of acetaldehyde was added and the reaction was continued for 1 hour. After completion of the reaction, the pH was adjusted to 8 with aqueous sodium bicarbonate, filtered and dried to obtain 1-methyl-7-methoxy-tetrahydro-β-carboline. The dried 1-methyl-7-methoxy-tetrahydro-β-carboline was transferred to another 100 mL round-bottom flask, 50 mL of toluene and 5% Pd/C catalyst were added, and the reaction was refluxed for 24 hours. At the end of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. Finally, it was purified by recrystallization from acetone to give 1-methyl-7-methoxy-β-carboline (3.6 mmol, 72% yield).

Store at RT

Crystallise harmine from MeOH and sublime it in a vacuum. See hydrochloride below. [Beilstein 23 II 348, 23 III/IV 2702, 23/12 V 237.]

[1] Angewandte Chemie - International Edition, 2013, vol. 52, # 27, p. 6983 - 6987
[2] Ross. Khim. Zh., 2013, vol. 125, # 27, p. 7121 - 7125,5
[3] Patent: CN104557916, 2017, B. Location in patent: Paragraph 0034-0036
[4] Chemische Berichte, 1930, vol. 63, p. 2245,2247
[5] Tetrahedron, 2002, vol. 58, # 31, p. 6185 - 6197