Hirsutine

Modify Date: 2024-01-04 18:56:01

Hirsutine structure	Common Name	Hirsutine
	CAS Number	7729-23-9	Molecular Weight	368.469
	Density	1.2±0.1 g/cm3	Boiling Point	531.7±50.0 °C at 760 mmHg
	Molecular Formula	C₂₂H₂₈N₂O₃	Melting Point	101℃
	MSDS	N/A	Flash Point	275.4±30.1 °C

Use of Hirsutine

Hirsutine, an indole alkaloid of Uncaria rhynchophylla, exhibits anti-cancer activity. Hirsutine induces apoptosis and is a potent Dengue virus inhibitor exhibiting low cytotoxicity[1][2][3].

Name	methyl (E)-2-[(2S,3R,12bR)-3-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate
Synonym	More Synonyms

Description	Hirsutine, an indole alkaloid of Uncaria rhynchophylla, exhibits anti-cancer activity. Hirsutine induces apoptosis and is a potent Dengue virus inhibitor exhibiting low cytotoxicity[1][2][3].
Related Catalog	Signaling Pathways >> Apoptosis >> Apoptosis Research Areas >> Cancer Research Areas >> Infection
In Vitro	Hirsutine remarkably reduces the viability of MCF-7 and MDA-MB-231 cells in a time- and dose-dependent manner with IC50 values of 447.79 and 179.06 μM, respectively. In the MDA-MB-231 cells, Hirsutine induces apoptosis and depolarization of MMP, releases Cyt C from mitochondria, and activates caspase 9 and caspase 3[2].
In Vivo	Hirsutine induces mPTP-dependent apoptosis through ROCK1/PTEN/PI3K/GSK3β pathway in human lung cancer cells[3].
References	[1]. Hishiki T, et al. Hirsutine, an Indole Alkaloid of Uncaria rhynchophylla, Inhibits Late Step in Dengue Virus Lifecycle. Front Microbiol. 2017 Aug 30;8:1674. [2]. Huang QW, et al. [Hirsutine induces apoptosis of human breast cancer MDA-MB-231 cells through mitochondrial pathway]. Sheng Li Xue Bao. 2018 Feb 25;70(1):40-46. [3]. Zhang R, et al. Hirsutine induces mPTP-dependent apoptosis through ROCK1/PTEN/PI3K/GSK3β pathway in human lung cancer cells. Cell Death Dis. 2018 May 22;9(6):598.

Density	1.2±0.1 g/cm3
Boiling Point	531.7±50.0 °C at 760 mmHg
Melting Point	101℃
Molecular Formula	C₂₂H₂₈N₂O₃
Molecular Weight	368.469
Flash Point	275.4±30.1 °C
Exact Mass	368.209991
PSA	54.56000
LogP	3.96
Vapour Pressure	0.0±1.4 mmHg at 25°C
Index of Refraction	1.613

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VS3660000

CHEMICAL NAME :: 17,18-Seco-3-beta-yohimban-16-carboxylic acid, 16,17-didehydro-17-methoxy-, methyl ester, (E)-

CAS REGISTRY NUMBER :: 7729-23-9

LAST UPDATED :: 198909

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C22-H28-N2-O3

MOLECULAR WEIGHT :: 368.52

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 110 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes

REFERENCE :: NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 94,17,1989

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 35 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - other changes

REFERENCE :: NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 94,17,1989

Indolo[2,3-a]quinolizine-2-acetic acid, 3-ethyl-1,2,3,4,6,7,12,12b-octahydro-α-(methoxymethylene)-, methyl ester, (αE,2S,3R,12bR)-

Methyl (3β,16E)-16-(methoxymethylene)corynan-17-oate

Hirsutine

Methyl (3β,16E)-17-methoxycoryn-16-en-16-carboxylate

methyl (3β,16E)-16-(methoxymethylidene)corynan-17-oate