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蓖麻碱

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蓖麻碱
IUPAC名
4-Methoxy-1-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile
别名 3-cyano-4-methoxy-N-methyl-2-pyridone
识别
CAS号 524-40-3
PubChem 10666
ChemSpider 10216
SMILES
 
  • Cn1ccc(c(c1=O)C#N)OC
3DMet B00311
ChEBI 18043
KEGG C01526
性质
化学式 C8H8N2O2
摩尔质量 164.16 g·mol−1
熔点 200 °C(473 K)
危险性
致死量或浓度:
LD50中位剂量
340 mg/kg[1]
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

蓖麻碱(英语:Ricinine),是从蓖麻中提取到的一种剧毒生物碱[2]。其可作为蓖麻毒蛋白生物标记[3][4]

蓖麻碱由Tuson于1864年在蓖麻籽中分离得到[5][6]

性质

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蓖麻碱在蓖麻幼芽、子叶中含量较高,为0.7-1%。蓖麻碱纯品为白色针状或棱柱状结晶体,在热水和热三氯甲烷中溶解度较高,但难溶于苯、乙醚和石油醚。其碱性溶液可使高锰酸钾还原,并伴随有氢氰酸的生成[7]

在碘或氯化汞溶液中会沉淀,但在Mayer试剂(碘化汞钾溶液)中不会沉淀[5]

蓖麻碱在碱性条件可水解产生甲醇和蓖麻碱酸(ricininic acid)[5]

生物作用

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蓖麻碱是一种剧毒生物碱,分子中含有氰基,具有较强的毒性,毒性反应主要有恶心、呕吐,严重者肝、肾受损,呼吸抑制死亡等。饲料中蓖麻碱含量高于 0.01%,可抑制鸡的生长;含量高于 0.1%,可致鸡中毒死亡[7]

蓖麻碱容易进入昆虫体内,触杀胃毒效果高[8],对作物植株还具有叶面追加有机肥源的效果[9]

参考文献

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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可免费查阅. PMID 22069699. doi:10.3390/toxins3101332可免费查阅. 
  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可免费查阅. PMID 24618672. doi:10.1371/journal.pone.0090416可免费查阅. 
  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可免费查阅. 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可免费查阅. 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. 
  7. ^ 7.0 7.1 霍玉淼,文艳鹏,包春光,等. 蓖麻毒素应用研究进展. 特种经济动植物. 2023, 26 (1): 79–101. 
  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可免费查阅. PMID 24996560. doi:10.1186/1756-3305-7-312可免费查阅. 
  9. ^ 吴莹、李希. 植物源农药蓖麻碱微乳剂技术指标的建立. 中药与临床. 2016, (04): 29–32. doi:10.3969/j.issn.1674-926X.2016.04.009.