去甲二氫駱駝蓬鹼

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 ; 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）; 212 °C（414 °F；485 K）（自由鹼）
	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]、乙酰膽鹼酯酶、丁酰膽鹼酯酶（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

^ Thieme Chemistry (Hrsg.): RÖMPP Online – Version 3.37. Georg Thieme Verlag KG, Stuttgart, 27. September 2013.
^ The alkaloids: chemistry and physiology. New York: Academic Press. 1965: 49. ISBN 978-0-08-086532-4.
^ 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.
^ ^4.0 ^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 . PMID 22037238. doi:10.1016/j.fct.2011.10.052.
^ ^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.
^ 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.
^ 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.
^ 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 .
^ 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.
^ 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.
^ 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.
^ Therapeutic Goods (Poisons Standard—October 2024) Instrument 2024. Federal Register of Legislation. 2024-09-30 [2024-12-02].

[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.

[pmid24368411-3] 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.

[pmid22037238-4] 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 . PMID 22037238. doi:10.1016/j.fct.2011.10.052.

[Herraiz-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 .

[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.

[Poisons_Standard-12] Therapeutic Goods (Poisons Standard—October 2024) Instrument 2024. Federal Register of Legislation. 2024-09-30 [2024-12-02].

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]