5-羥色氨酸

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5-羥色氨酸
Skeletal formula
Ball-and-stick model
IUPAC名
2-amino-3- (5-hydroxy-1H-indol-3-yl) propanoic acid
識別
CAS號 56-69-9
PubChem 144
ChemSpider 388413
SMILES
InChI
InChIKey LDCYZAJDBXYCGN-VIFPVBQEBZ
ChEBI 17780
KEGG D07339
MeSH 5-Hydroxytryptophan
ATC代碼 N06AX01
性質
化學式 C11H12N2O3
摩爾質量 220.23 g/mol g·mol⁻¹
密度 1.484 g/mL
熔點 298-300 °C(571-573 K)
沸點 520.6 °C(794 K)
若非註明,所有數據均出自一般條件(25 ℃,100 kPa)下。

5-羥色氨酸(英語:5-Hydroxytryptophan,5-HTP),(INN商品名:oxitriptan )是一種天然胺基酸代謝中間產物,同時也是神經遞質5-羥色胺褪黑素生物合成前體

5-羥色氨酸在美英以及加拿大以非處方藥方式出售,作為幫助抑鬱症厭食症失眠患者的膳食補充劑,同時也作為治療重性抑鬱障礙的藥物在歐洲許多國家銷售。[1][2]幾個安慰劑雙盲臨床試驗已證明5-HTP有治療抑鬱症的效果[1],但缺乏極顯著性[3],需要更進一步的大量臨床對照研究[4]

目錄

代謝

5-羥色氨酸由芳香族L-胺基酸脫羧酶維生素B6幫助下脫羧為血清素(5-羥色胺,5-HT)[5]。該反應在神經組織肝臟細胞中發生[6]。 5-羥色氨酸可以穿過血腦屏障[7],但5-羥色胺不能。過量的5-羥色氨酸會被代謝排出體外,特別是體內存在維生素B6時。[8][9]

5-HTP AAAD 血清素
5-Hydroxy-L-Tryptophan (5-HTP).svg   Serotonin (5-HT).svg
磷酸吡哆醛
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藥理學

5-羥色氨酸對中樞神經系統的作用在於其增加了血清素的生產[10]

Metabolic pathway from tryptophan to serotonin.

另見

參考文獻

  1. 1.0 1.1 Turner EH, Blackwell AD. 5-Hydroxytryptophan plus SSRIs for interferon-induced depression: synergistic mechanisms for normalizing synaptic serotonin. Medical Hypotheses. 2005, 65 (1): 138–44. doi:10.1016/j.mehy.2005.01.026. PMID 15893130. 
  2. Swiss Pharmaceutical Society. Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. 2000. ISBN 3-88763-075-0. 
  3. Shaw K, Turner J, Del Mar CShaw, Kelly A. . Tryptophan and 5-hydroxytryptophan for depression. Cochrane Database of Systematic Reviews (Online). 2002 (1): CD003198. doi:10.1002/14651858.CD003198. PMID 11869656. 
  4. 5-Hydroxytryptophan (5-HTP) University of Maryland Medical Center. 2011. Accessed: 9 January 2012.
  5. Rahman MK, Nagatsu T, Sakurai T, Hori S, Abe M, Matsuda M. Effect of pyridoxal phosphate deficiency on aromatic L-amino acid decarboxylase activity with L-DOPA and L-5-hydroxytryptophan as substrates in rats. Jpn. J. Pharmacol.. 1982, 32 (5): 803–11. doi:10.1254/jjp.32.803. PMID 6983619. 
  6. Bouchard, S; Bousquet, C; Roberge, AG. Characteristics of dihydroxyphenylalanine/5-hydroxytryptophan decarboxylase activity in brain and liver of cat. Journal of Neurochemistry. 1981, 37 (3): 781–7. doi:10.1111/j.1471-4159.1982.tb12555.x. PMID 6974228. 
  7. Gomes P, Soares-da-Silva P.. L-DOPA transport properties in an immortalised cell line of rat capillary cerebral endothelial cells, RBE 4. Brain Res.. 1999, 829 (1–2): 143–150. doi:10.1016/S0006-8993(99)01387-6. PMID 18445233. 
  8. Bouchard S, Roberge AG. Biochemical properties and kinetic parameters of dihydroxyphenylalanine--5-hydroxytryptophan decarboxylase in brain, liver, and adrenals of cat. Can. J. Biochem.. 1979, 57 (7): 1014–8. doi:10.1139/o79-126. PMID 39668. 
  9. Amamoto T, Sarai K. On the tryptophan-serotonin metabolism in manic-depressive disorders. Changes in plasma 5-HT and 5-HIAA levels and urinary 5-HIAA excretion following oral loading of L-5HTP in patients with depression. Hiroshima J. Med. Sci.. 1976, 25 (2–3): 135–40. PMID 1088369. 
  10. 5-HTP: Uses, Side Effects, Interactions and Warnings - WebMD [2009-10-05] (原始內容存檔於16 November 2009). 

進一步閱讀

Template:Hypnotics

Template:Serotonergics

參考來源

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