維基百科

四氫異喹啉

化合物

四氫異喹啉（英文：Tetrahydroisoquinoline，縮寫：TIQ或THIQ）是一種有機化合物，化學式為C9H11N。它屬於仲胺類，由異喹啉經氫化而得。它是一種無色粘稠液體，可與大多數有機溶劑混溶。在許多生物活性化合物和藥物中都會遇到四氫異喹啉結構。[1][2]

四氫異喹啉
IUPAC名
1,2,3,4-Tetrahydroisoquinoline
識別
縮寫 TIQ, THIQ
CAS號 91-21-4  checkY
PubChem 7046
ChemSpider 6779
SMILES
 
  • c1ccc2c(c1)CCNC2
InChI
 
  • 1/C9H11N/c1-2-4-9-7-10-6-5-8(9)3-1/h1-4,10H,5-7H2
InChIKey UWYZHKAOTLEWKK-UHFFFAOYAB
RTECS NX4900000
性質
化學式 C9H11N
莫耳質量 133.19 g·mol⁻¹
外觀 深黃色液體
密度 1.05 g/mL
熔點 -30 °C（243 K）
沸點 235 - 239 °C（269 K）
危險性
GHS危險性符號
《全球化學品統一分類和標籤制度》（簡稱「GHS」）中腐蝕性物質的標籤圖案《全球化學品統一分類和標籤制度》（簡稱「GHS」）中有毒物質的標籤圖案《全球化學品統一分類和標籤制度》（簡稱「GHS」）中對人體有害物質的標籤圖案
GHS提示詞 Danger
H-術語 H301, H310, H314, H332, H371, H412
P-術語 P260, P261, P262, P264, P270, P271, P273, P280, P301+310, P301+330+331, P302+350, P302+352, P303+361+353, P304+312
若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

反應

作為仲胺，四氫異喹啉具有弱鹼性，與強酸形成鹽。四氫異喹啉脫氫可生成異喹啉，加氫可生成十氫異喹啉。與其他仲胺一樣，四氫異喹啉可以在二氧化硒的催化下使用過氧化氫氧化成相應的硝酮。[3]

毒理學

四氫異喹啉的衍生物可能作為某些藥物的代謝產物在體內形成，這曾被認為與酒精中毒的發展有關。[4]這一理論現在已被質疑，不再被科學界普遍接受，[5]但神經毒性四氫異喹啉的衍生物（如norsalsolinol）的內源性生產仍然被研究為帕金森氏病等某些疾病的可能原因。[6][7][8][9][10][11]

四氫異喹啉

四氫異喹啉結構存在於許多藥物中，[12]例如筒箭毒鹼（種神經肌肉阻滯藥）。基於4-取代四氫異喹啉的藥物包括諾米芬辛[13]和雙氯芬辛。它們可以通過苄胺與鹵化苯乙酮的N-烷基化來製備。[14]天然存在的四氫異喹啉包括車瑞靈[15]和寬葉啉。

Esproquin[16]由四氫異喹啉製成，憑藉其α-腎上腺素能阻滯特性顯示出降壓活性。

參考文獻

  1. ^ Mitchenson, Andrew. Saturated nitrogen heterocycles. Journal of the Chemical Society, Perkin Transactions 1. 2000, (17): 2862–2892. doi:10.1039/A908537H. 
  2. ^ Scott, Jack D.; Williams, Robert M. Chemistry and Biology of the Tetrahydroisoquinoline Antitumor Antibiotics. Chemical Reviews. 2002, 102 (5): 1669–1730. PMID 11996547. doi:10.1021/cr010212u. 
  3. ^ Murahashi, S. Selenium dioxide catalyzed oxidation of secondary amines with hydrogen peroxide. Simple synthesis of nitrones from secondary amines. Tetrahedron Letters. 1987, 28 (21): 2383–2386. doi:10.1016/S0040-4039(00)96130-6. 
  4. ^ Blum, K.; Hamilton, M. G.; Hirst, M.; Wallace, J. E. Putative role of isoquinoline alkaloids in alcoholism: a link to opiates. Alcoholism: Clinical and Experimental Research. 1978, 2 (2): 113–120. PMID 350073. doi:10.1111/j.1530-0277.1978.tb04710.x. ,Altshuler, H. L.; Shippenberg. Tetrahydroisoquinoline and opioid substrates of alcohol actions. Progress in Clinical and Biological Research. 1982, 90: 329–344. PMID 7202207. , Myers, R. D. Isoquinolines, beta-carbolines and alcohol drinking: involvement of opioid and dopaminergic mechanisms. Experientia. 1989, 45 (5): 436–443. PMID 2656285. S2CID 1513683. doi:10.1007/BF01952025. 
  5. ^ Myers, R. D. Tetrahydroisoquinolines and alcoholism: where are we today?. Alcoholism: Clinical and Experimental Research. 1996, 20 (3): 498–500. PMID 8727243. doi:10.1111/j.1530-0277.1996.tb01081.x. , Musshoff, F.; Daldrup, T.; Bonte, W.; Leitner, A.; Lesch, O. M. Formaldehyde-derived tetrahydroisoquinolines and tetrahydro-beta-carbolines in human urine. Journal of Chromatography B. 1996, 683 (2): 163–176. PMID 8891913. doi:10.1016/0378-4347(96)00106-5. , Sällström Baum, S.; Hill, R.; Kiianmaa, K.; Rommelspacher, H. Effect of ethanol on (R)- and (S)-salsolinol, salsoline, and THP in the nucleus accumbens of AA and ANA rats. Alcohol (Fayetteville, N.Y.). 1999, 18 (2–3): 165–169. PMID 10456568. doi:10.1016/S0741-8329(98)00080-9. , Musshoff, F.; Lachenmeier, D. W.; Schmidt, P.; Dettmeyer, R.; Madea, B. Systematic regional study of dopamine, norsalsolinol, and (R/S)-salsolinol levels in human brain areas of alcoholics. Alcoholism: Clinical and Experimental Research. 2005, 29 (1): 46–52. PMID 15654290. doi:10.1097/01.ALC.0000150011.81102.C2. 
  6. ^ Kotake Y, Tasaki Y, Makino Y, Ohta S, Hirobe M. 1-Benzyl-1,2,3,4-tetrahydroisoquinoline as a parkinsonism-inducing agent: a novel endogenous amine in mouse brain and parkinsonian CSF. Journal of Neurochemistry. December 1995, 65 (6): 2633–8. PMID 7595560. S2CID 39449026. doi:10.1046/j.1471-4159.1995.65062633.x. 
  7. ^ McNaught KS, Carrupt PA, Altomare C, Cellamare S, Carotti A, Testa B, Jenner P, Marsden CD. Isoquinoline derivatives as endogenous neurotoxins in the aetiology of Parkinson's disease. Biochemical Pharmacology. October 1998, 56 (8): 921–33. PMID 9776302. doi:10.1016/S0006-2952(98)00142-7. 
  8. ^ Lorenc-Koci E, Smiałowska M, Antkiewicz-Michaluk L, Gołembiowska K, Bajkowska M, Wolfarth S. Effect of acute and chronic administration of 1,2,3,4-tetrahydroisoquinoline on muscle tone, metabolism of dopamine in the striatum and tyrosine hydroxylase immunocytochemistry in the substantia nigra, in rats. Neuroscience. 2000, 95 (4): 1049–59. PMID 10682712. S2CID 13549697. doi:10.1016/S0306-4522(99)00511-4. 
  9. ^ Storch A, Ott S, Hwang YI, Ortmann R, Hein A, Frenzel S, Matsubara K, Ohta S, Wolf HU, Schwarz J. Selective dopaminergic neurotoxicity of isoquinoline derivatives related to Parkinson's disease: studies using heterologous expression systems of the dopamine transporter. Biochemical Pharmacology. March 2002, 63 (5): 909–20. PMID 11911843. doi:10.1016/S0006-2952(01)00922-4. 
  10. ^ Lorenc-Koci E, Antkiewicz-Michaluk L, Kamińska A, Lenda T, Zieba B, Wierońska J, Smiałowska M, Schulze G, Rommelspacher H. The influence of acute and chronic administration of 1,2-dimethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline on the function of the nigrostriatal dopaminergic system in rats. Neuroscience. October 2008, 156 (4): 973–86. PMID 18809471. S2CID 44658852. doi:10.1016/j.neuroscience.2008.08.050. 
  11. ^ Kobayashi H, Fukuhara K, Tada-Oikawa S, Yada Y, Hiraku Y, Murata M, Oikawa S. The mechanisms of oxidative DNA damage and apoptosis induced by norsalsolinol, an endogenous tetrahydroisoquinoline derivative associated with Parkinson's disease. Journal of Neurochemistry. January 2009, 108 (2): 397–407. PMID 19012744. doi:10.1111/j.1471-4159.2008.05774.x  . 
  12. ^ Scott, Jack D.; Williams, Robert M. Chemistry and Biology of the Tetrahydroisoquinoline Antitumor Antibiotics. Chemical Reviews. 2002, 102 (5): 1669–1730. PMID 11996547. doi:10.1021/cr010212u. 
  13. ^ Schneider, C. S.; Weber, K. H.; Daniel, H.; Bechtel, W. D.; Boeke-Kuhn, K. Synthesis and antidepressant activity of 4-aryltetrahydrothieno[2,3-c]pyridine derivatives. Journal of Medicinal Chemistry. 1984, 27 (9): 1150–1155. PMID 6471069. doi:10.1021/jm00375a011. 
  14. ^ BG 49761 
  15. ^ cherylline. [2022-12-10]. （原始內容存檔於2022-12-10）. 
  16. ^ Gray, Allan P.; Shiley, Richard H. Preparation and cardiovascular actions of a group of tetrahydroisoquinoline derivatives. Journal of Medicinal Chemistry. 1973, 16 (7): 859–861. ISSN 0022-2623. PMID 4146907. doi:10.1021/jm00265a028. 
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