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SML3507

Sigma-Aldrich

Hirsutine

≥98% (HPLC)

Synonym(s):

(αE,​2S,​3R,​12bR)​-3-​Ethyl-​1,​2,​3,​4,​6,​7,​12,​12b-​octahydro-​α-​(methoxymethylene)​-indolo[2,​3-​a]​quinolizine-​2-​acetic acid methyl ester, (E)-16,17-Didehydro-17-methoxy-17,18-seco-3-beta-yohimban-16-carboxylic acid methyl ester

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About This Item

Empirical Formula (Hill Notation):
C22H28N2O3
CAS Number:
7729-23-9
Molecular Weight:
368.47
MDL number:
MFCD01750089
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

-10 to -25°C

SMILES string

CC[C@@]1([H])CN(CCC2=C3NC4=C2C=CC=C4)[C@]3([H])C[C@]1([H])/C(C(OC)=O)=C\OC

InChI

1S/C22H28N2O3/c1-4-14-12-24-10-9-16-15-7-5-6-8-19(15)23-21(16)20(24)11-17(14)18(13-26-2)22(25)27-3/h5-8,13-14,17,20,23H,4,9-12H2,1-3H3/b18-13+/t14-,17-,20+/m0/s1

InChI key

NMLUOJBSAYAYEM-AZQGJTAVSA-N

Biochem/physiol Actions

Hirsutine is a brain penetrant alkaloid from Uncaria rhynchophylla that exhibit anti-cancer, cardioprotective, anti-hypertensive, and anti-arrhythmic activities. It appears that hirsutine induces apoptosis in lung cancer cells through opening of mitochondrial permeability transition pore (mPTP). Hirsutine exhibit potent anti-dengue virus activity.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The Blood-Brain Barrier Permeability of Six Indole Alkaloids from Uncariae Ramulus Cum Uncis in the MDCK-pHaMDR Cell Monolayer Model.
Zhang YN, Yang YF, Xu W, Yang XW
Biomolecules, 22, 1944-1944 (2017)
Takayuki Hishiki et al.
Frontiers in microbiology, 8, 1674-1674 (2017-09-16)
Dengue virus (DENV) is transmitted to humans by Aedes mosquitoes and is a public health issue worldwide. No antiviral drugs specific for treating dengue infection are currently available. To identify novel DENV inhibitors, we analyzed a library of 95 compounds
Rong Zhang et al.
Cell death & disease, 9(6), 598-598 (2018-05-24)
Hirsutine extracted from Uncaria rhynchophylla has been shown to exhibit anti-cancer activity. However, the molecular mechanism by which hirsutine exhibits anti-lung cancer activity remains unclear. In the present study, we showed that hirsutine induces apoptosis in human lung cancer cells

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