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去甲二氫駱駝蓬鹼

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去甲二氫駱駝蓬鹼
IUPAC名
1-Methyl-4,9-dihydro-3H-pyrido[4,3-b]indol-7-ol
別名 1-甲基-4,9-二氫-3H-β-咔啉-7-醇
識別
CAS號 525-57-5  checkY
6028-07-5（鹽酸鹽）
6028-00-8（鹽酸鹽二水合物）
PubChem 5353656
ChemSpider 11262879
SMILES
 
  • OC1=CC=C(C(CCN=C3C)=C3N2)C2=C1
EINECS 208-375-4
性質
化學式 C12H12N2O
摩爾質量 200.24 g·mol−1
熔點 100—105 °C（212—221 °F；373—378 K）（三水合物）[1]
212 °C（414 °F；485 K）（自由鹼）[2]
若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

去甲二氫駱駝蓬鹼是一種β-咔啉的衍生物，也是一種駱駝蓬生物鹼（英語：harmala alkaloid）。[3][4]它存在於駱駝蓬種子中，含量為0.6%[5]—3.90%[6]。它也存在於死藤水中，但含量遠少於其它生物鹼。[7]

去甲二氫駱駝蓬鹼是單胺氧化酶A（英語：Monoamine oxidase A）[5]、乙醯膽鹼酯酶、丁醯膽鹼酯酶（英語：Butyrylcholinesterase）[8]及致癌的CYP1A1（英語：CYP1A1）的抑制劑。[4]它也用於研究DNA、RNA與生物鹼結合的研究。[9][10]對血壓正常、麻醉後的狗做的實驗顯示去甲二氫駱駝蓬鹼會降低心率，升高脈壓、主動脈血流量、心肌收縮力（英語：Myocardial contractility）。[11]

去甲二氫駱駝蓬鹼和其它駱駝蓬生物一樣，列於澳大利亞出台的藥物和毒物的統一調度標準的第9類物質中，即受管制物質，除科學研究外的其它用途都是犯法的。[12]

參見

參考資料

  1. ^ Thieme Chemistry (Hrsg.): RÖMPP Online – Version 3.37. Georg Thieme Verlag KG, Stuttgart, 27. September 2013.
  2. ^ The alkaloids: chemistry and physiology. New York: Academic Press. 1965: 49. ISBN 978-0-08-086532-4. 
  3. ^ Sarkar S, Bhadra K. Binding of alkaloid harmalol to DNA: photophysical and calorimetric approach.. J Photochem Photobiol B. 2014, 130: 272–80. PMID 24368411. doi:10.1016/j.jphotobiol.2013.11.021. 
  4. ^ 4.0 4.1 El Gendy MA, Soshilov AA, Denison MS, El-Kadi AO. Harmaline and harmalol inhibit the carcinogen-activating enzyme CYP1A1 via transcriptional and posttranslational mechanisms.. Food Chem Toxicol. 2012, 50 (2): 353–62. PMC 3281145 可免費查閱. PMID 22037238. doi:10.1016/j.fct.2011.10.052. 
  5. ^ 5.0 5.1 Herraiz, T.; González, D.; Ancín-Azpilicueta, C.; Arán, V. J.; Guillén, H. beta-Carboline alkaloids in Peganum harmala and inhibition of human monoamine oxidase (MAO). Food and Chemical Toxicology: An International Journal Published for the British Industrial Biological Research Association. 2010, 48 (3): 839–845. ISSN 1873-6351. PMID 20036304. doi:10.1016/j.fct.2009.12.019. 
  6. ^ Hemmateenejad, Bahram; Abbaspour, Abdolkarim; Maghami, Homeyra; Miri, Ramin; Panjehshahin, Mohhamad Reza. Partial least squares-based multivariate spectral calibration method for simultaneous determination of beta-carboline derivatives in Peganum harmala seed extracts. Analytica Chimica Acta. 2006-08-11, 575 (2): 290–299. ISSN 1873-4324. PMID 17723604. doi:10.1016/j.aca.2006.05.093. 
  7. ^ McIlhenny, Ethan H.; Pipkin, Kelly E.; Standish, Leanna J.; Wechkin, Hope A.; Strassman, Rick; Barker, Steven A. Direct analysis of psychoactive tryptamine and harmala alkaloids in the Amazonian botanical medicine ayahuasca by liquid chromatography–electrospray ionization-tandem mass spectrometry. Journal of Chromatography A. 2009, 1216 (51): 8960–8968. PMID 19926090. doi:10.1016/j.chroma.2009.10.088. 
  8. ^ Zhao, Ting; Ding, Ke-min; Zhang, Lei; Cheng, Xue-mei; Wang, Chang-hong; Wang, Zheng-tao. Acetylcholinesterase and Butyrylcholinesterase Inhibitory Activities of β ‐Carboline and Quinoline Alkaloids Derivatives from the Plants of Genus Peganum. Journal of Chemistry. 2013, 2013 (1). ISSN 2090-9063. doi:10.1155/2013/717232 可免費查閱. 
  9. ^ Nafisi, Shohreh; Malekabady, Zahra Mokhtari; Khalilzadeh, Mohammad Ali. Interaction of β-carboline alkaloids with RNA. DNA and cell biology. 2010, 29 (12): 753–761. ISSN 1557-7430. PMID 20731607. doi:10.1089/dna.2010.1087. 
  10. ^ Nafisi, Shohreh; Bonsaii, Mahyar; Maali, Pegah; Khalilzadeh, Mohammad Ali; Manouchehri, Firouzeh. Beta-carboline alkaloids bind DNA. Journal of Photochemistry and Photobiology. B, Biology. 2010-08-02, 100 (2): 84–91. ISSN 1873-2682. PMID 20541950. doi:10.1016/j.jphotobiol.2010.05.005. 
  11. ^ Aarons, Darryl H.; Victor Rossi, G.; Orzechowski, Raymond F. Cardiovascular Actions of Three Harmala Alkaloids: Harmine, Harmaline, and Harmalol. Journal of Pharmaceutical Sciences. 1977, 66 (9): 1244–1248. doi:10.1002/jps.2600660910. 
  12. ^ Therapeutic Goods (Poisons Standard—October 2024) Instrument 2024. Federal Register of Legislation. 2024-09-30 [2024-12-02]. 
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