蓖麻鹼

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
	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的生物標記^[3]^[4]。

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蓖麻鹼由Tuson於1864年在蓖麻籽中分離得到^[5]^[6]。

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]。

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]。

[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 . PMID 22069699. doi:10.3390/toxins3101332 .
[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 . PMID 24618672. doi:10.1371/journal.pone.0090416 .
[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 . 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 . PMID 23471955. doi:10.1093/jat/bkt010.
[5]
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]
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.
[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 . PMID 24996560. doi:10.1186/1756-3305-7-312 .
[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.

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[1] [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 . PMID 22069699. doi:10.3390/toxins3101332 .

[2] [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 . PMID 24618672. doi:10.1371/journal.pone.0090416 .

[3] [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 . PMID 23014889. doi:10.1093/jat/bks077.

[4] [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 . PMID 23471955. doi:10.1093/jat/bkt010.

[henry-5] [5]
Henry, Thomas Anderson. Ricinine. The Plant Alkaloids 4th. The Blakiston Company. 1949: 5.

[6] [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.

[ds-7] [7]
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.

[8] [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 . PMID 24996560. doi:10.1186/1756-3305-7-312 .

[9] [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.

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[9]

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蓖麻鹼

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性質

生物作用

參考文獻

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。