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蓖麻鹼

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蓖麻鹼
IUPAC名
4-Methoxy-1-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
別名 3-cyano-4-methoxy-N-methyl-2-pyridone
識別
CAS號 524-40-3
PubChem 10666
ChemSpider 10216
SMILES
 
  • Cn1ccc(c(c1=O)C#N)OC
3DMet B00311
ChEBI 18043
KEGG C01526
性質
化學式 C8H8N2O2
摩爾質量 164.16 g·mol−1
熔點 200 °C(473 K)
危險性
致死量或濃度:
LD50中位劑量
340 mg/kg[1]
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

蓖麻鹼(英語:Ricinine),是從蓖麻中提取到的一種劇毒生物鹼[2]。其可作為蓖麻毒蛋白生物標記[3][4]

蓖麻鹼由Tuson於1864年在蓖麻籽中分離得到[5][6]

性質

[編輯]

蓖麻鹼在蓖麻幼芽、子葉中含量較高,為0.7-1%。蓖麻鹼純品為白色針狀或稜柱狀結晶體,在熱水和熱三氯甲烷中溶解度較高,但難溶於苯、乙醚和石油醚。其鹼性溶液可使高錳酸鉀還原,並伴隨有氫氰酸的生成[7]

在碘或氯化汞溶液中會沉澱,但在Mayer試劑(碘化汞鉀溶液)中不會沉澱[5]

蓖麻鹼在鹼性條件可水解產生甲醇和蓖麻鹼酸(ricininic acid)[5]

生物作用

[編輯]

蓖麻鹼是一種劇毒生物鹼,分子中含有氰基,具有較強的毒性,毒性反應主要有噁心、嘔吐,嚴重者肝、腎受損,呼吸抑制死亡等。飼料中蓖麻鹼含量高於 0.01%,可抑制雞的生長;含量高於 0.1%,可致雞中毒死亡[7]

蓖麻鹼容易進入昆蟲體內,觸殺胃毒效果高[8],對作物植株還具有葉面追加有機肥源的效果[9]

參考文獻

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  1. ^ Worbs, Sylvia; Köhler, Kernt; Pauly, Diana; Avondet, Marc-André; Schaer, Martin; Dorner, Martin B.; Dorner, Brigitte G. Ricinus communis Intoxications in Human and Veterinary Medicine—A Summary of Real Cases. Toxins. 24 October 2011, 3 (10): 1332–1372. PMC 3210461可免費查閱. PMID 22069699. doi:10.3390/toxins3101332可免費查閱. 
  2. ^ Peng, Jing; Cai, Shuang; Wang, Lin; Zhao, Nan; Zhang, Ting-jian; Chen, Zai-xing; Meng, Fan-hao; Dzeja, Petras. A Metabonomic Analysis of Serum from Rats Treated with Ricinine Using Ultra Performance Liquid Chromatography Coupled with Mass Spectrometry. PLOS ONE. 11 March 2014, 9 (3): e90416. Bibcode:2014PLoSO...990416P. PMC 3949718可免費查閱. PMID 24618672. doi:10.1371/journal.pone.0090416可免費查閱. 
  3. ^ Hamelin, Elizabeth I.; Johnson, Rudolph C.; Osterloh, John D.; Howard, David J.; Thomas, Jerry D. Evaluation of Ricinine, a Ricin Biomarker, from a Non-Lethal Castor Bean Ingestion. Journal of Analytical Toxicology. November 2012, 36 (9): 660–662. PMC 4561852可免費查閱. PMID 23014889. doi:10.1093/jat/bks077. 
  4. ^ Pittman, C. T.; Guido, J. M.; Hamelin, E. I.; Blake, T. A.; Johnson, R. C. Analysis of a Ricin Biomarker, Ricinine, in 989 Individual Human Urine Samples. Journal of Analytical Toxicology. 6 March 2013, 37 (4): 237–240. PMC 4547525可免費查閱. PMID 23471955. doi:10.1093/jat/bkt010. 
  5. ^ 5.0 5.1 5.2 Henry, Thomas Anderson. Ricinine. The Plant Alkaloids 4th. The Blakiston Company. 1949: 5. 
  6. ^ Rao, N. V. Subra. A Note on the Chemical Composition of Castor Leaves. Proceedings of the Indian Academy of Sciences. Feb 12, 1945, A (21): 123–125 [Aug 7, 2021]. S2CID 94199266. doi:10.1007/BF03051280. (原始內容存檔於2021-08-07). 
  7. ^ 7.0 7.1 霍玉淼,文艷鵬,包春光,等. 蓖麻毒素应用研究进展. 特種經濟動植物. 2023, 26 (1): 79–101 [2024-07-14]. (原始內容存檔於2024-07-14). 
  8. ^ Wachira, Sabina; Omar, Sabar; Jacob, Julia; Wahome, Martin; Alborn, Hans T; Spring, David R; Masiga, Daniel K; Torto, Baldwyn. Toxicity of six plant extracts and two pyridone alkaloids from Ricinus communis against the malaria vector Anopheles gambiae. Parasites & Vectors. 2014, 7 (1): 312. PMC 4098926可免費查閱. PMID 24996560. doi:10.1186/1756-3305-7-312可免費查閱. 
  9. ^ 吳瑩、李希. 植物源农药蓖麻碱微乳剂技术指标的建立. 中藥與臨床. 2016, (04): 29–32. doi:10.3969/j.issn.1674-926X.2016.04.009.