Introduction：Basic information about CAS 7729-23-9|Hirsutine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Hirsutine |
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| CAS Number | 7729-23-9 | Molecular Weight | 368.469 |
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| Density | 1.2±0.1 g/cm3 | Boiling Point | 531.7±50.0 °C at 760 mmHg |
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| Molecular Formula | C22H28N2O3 | Melting Point | 101℃ |
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| MSDS | / | Flash Point | 275.4±30.1 °C |
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Names
| 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 |
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| Synonym | More Synonyms |
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Hirsutine BiologicalActivity
| 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]. |
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| Related Catalog | Signaling Pathways >>Apoptosis >>ApoptosisResearch Areas >>CancerResearch Areas >>Infection |
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| 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]. |
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| In Vivo | Hirsutine induces mPTP-dependent apoptosis through ROCK1/PTEN/PI3K/GSK3β pathway in human lung cancer cells[3]. |
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| 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. |
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Chemical & Physical Properties
| Density | 1.2±0.1 g/cm3 |
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| Boiling Point | 531.7±50.0 °C at 760 mmHg |
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| Melting Point | 101℃ |
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| Molecular Formula | C22H28N2O3 |
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| Molecular Weight | 368.469 |
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| Flash Point | 275.4±30.1 °C |
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| Exact Mass | 368.209991 |
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| PSA | 54.56000 |
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| LogP | 3.96 |
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| Vapour Pressure | 0.0±1.4 mmHg at 25°C |
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| Index of Refraction | 1.613 |
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| InChIKey | NMLUOJBSAYAYEM-AZQGJTAVSA-N |
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| SMILES | CCC1CN2CCc3c([nH]c4ccccc34)C2CC1C(=COC)C(=O)OC |
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Toxicological Information
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 DATAACUTE 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
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Synonyms
| 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 |
