Higenamine hydrochloride

• CAT Number: I007207
• CAS Number: 11041-94-4
• Molecular Formula: C16H18ClNO3
• Molecular Weight: 307.77
• Purity: ≥95%
• Synonyms: 1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol;hydrochloride
• InChI: InChI=1S/C16H17NO3.ClH/c18-12-3-1-10(2-4-12)7-14-13-9-16(20)15(19)8-11(13)5-6-17-14;/h1-4,8-9,14,17-20H,5-7H2;1H
• InChIKey: SWWQQSDRUYSMAR-UHFFFAOYSA-N
• SMILES: C1CNC(C2=CC(=C(C=C21)O)O)CC3=CC=C(C=C3)O.Cl

Higenamine hydrochloride is a selective LSD1 inhibitor (IC50=1.47 μM) that can be isolated from aconite. Higenamine hydrochloride has anti-inflammatory and antibacterial activity. Higenamine (Norcoclaurine) can attenuate IL-1β-induced Apoptosis through ROS-mediated PI3K/Akt signaling pathway. Higenamine hydrochloride protects brain cells from oxygen deprivation. Higenamine can promote bone formation in osteoporosis through the SMAD2/3 pathway. Higenamine hydrochloride can be used to study cancer, inflammation, cardiorenal syndrome and other diseases[1][2][3][4][5][6].
Higenamine hydrochloride (3-100 μM; 72 h) can inhibit the differentiation of MV4-11 and MOLM-13 cells by inhibiting the activity of LSD1[1].
Higenamine hydrochloride (1-100μM; 8 h) can enhance the activity of HO-1 in C6 cells and protect brain cells from cell hypoxia damage [2].
Higenamine hydrochloride (10-50 μM; 8 h) can inhibit apoptosis in C6 cells[2].
Higenamine hydrochloride (10-40 μM; 24 h) can inhibit the production of IL-1β-induced ROS and activate the ROS-mediated PI3K/Akt signaling pathway, which has anti-apoptotic activity in HNPCs[3].
Higenamine hydrochloride (0.08-250 μM; 0.5-24 h) promotes phosphorylation of SMAD2/3 in a time- and dose-dependent manner in BMSCs[6].
Higenamine hydrochloride (10 mg/kg; Intraperitoneal injection; Single dose) can significantly reduce the inflammation and infarct size of cerebral ischemic injury caused by middle cerebral artery occlusion (MCAO) in Sprague-Dawley rats[2].
Higenamine hydrochloride (0.5-4.5 mg/kg; Single dose) improves cardiac and renal function in rats with cardio-renal syndrome (CRS) and alleviates cardiac and renal fibrosis by targeting ASK1/MAPK (ERK, P38)/NF-kB signaling pathway in Sprague-Dawley rats[4].
Higenamine hydrochloride (20 mg/kg-30 mg/kg; Intraperitoneal injection; Once daily for 60 days) promotes bone formation and prevents accelerated bone loss in SAMP6 mice[6].

Reference

[1]. Fang Y, et al. Discovery of higenamine as a potent, selective and cellular active natural LSD1 inhibitor for MLL-rearranged leukemia therapy. Bioorg Chem. 2021 Apr;109:104723.
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[2]. Ha YM, et al. Higenamine reduces HMGB1 during hypoxia-induced brain injury by induction of heme oxygenase-1 through PI3K/Akt/Nrf-2 signal pathways. Apoptosis. 2012 May;17(5):463-74.
 [Content Brief]

[3]. Zhu X, et al. Higenamine mitigates interleukin-1β-induced human nucleus pulposus cell apoptosis by ROS-mediated PI3K/Akt signaling. Mol Cell Biochem. 2021 Nov;476(11):3889-3897.
 [Content Brief]

[4]. Deng T, et al. Higenamine Improves Cardiac and Renal Fibrosis in Rats With Cardiorenal Syndrome via ASK1 Signaling Pathway. J Cardiovasc Pharmacol. 2020 Jun;75(6):535-544.
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[5]. Erasto, Paul et al. Evaluation of Antimycobacterial Activity of Higenamine Using Galleria mellonella as an In Vivo Infection Model. Natural products and bioprospecting vol. 8,1 (2018): 63-69.
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[6]. Dong, Hui et al. Higenamine Promotes Osteogenesis Via IQGAP1/SMAD4 Signaling Pathway and Prevents Age- and Estrogen-Dependent Bone Loss in Mice. Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research vol. 38,5 (2023): 775-791.
 [Content Brief]