5-羟色氨酸

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提示:本条目的主题不是血清素(5-羟色胺,5-HT)。
5-羟色氨酸
Skeletal formula
球棍模型
IUPAC名
2-amino-3- (5-hydroxy-1H-indol-3-yl) propanoic acid
识别
CAS号 56-69-9  ✓
PubChem 144
ChemSpider 388413
SMILES
InChI
InChIKey LDCYZAJDBXYCGN-VIFPVBQEBZ
ChEBI 17780
KEGG D07339
MeSH 5-Hydroxytryptophan
ATC代码 N06AX01
性质
化学式 C11H12N2O3
摩尔质量 220.23 g/mol g·mol⁻¹
密度 1.484 g/mL
熔点 298-300 °C(571-573 K)
沸点 520.6 °C(794 K)
若非注明,所有数据均出自一般条件(25 ℃,100 kPa)下。

5-羟色氨酸英语:5-Hydroxytryptophan, 5-HTP;INN商品名:oxitriptan)是一种天然氨基酸代谢中间产物,同时也是神经递质5-羟色胺褪黑素生物合成前体

5-羟色氨酸在美英以及加拿大以非处方方式出售,作为帮助抑郁症、厌食症及失眠患者的膳食补充剂,同时也作为治疗重性抑郁障碍的药物在欧洲许多国家销售。[1][2]几个安慰剂双盲临床试验已证明5-HTP有治疗抑郁症的效果[1],但缺乏极显著性[3],需要更进一步的大量临床对照研究[4]

代谢[编辑]

5-羟色氨酸由芳香族L-氨基酸脱羧酶维生素B6帮助下脱羧血清素(5-羟色胺)[5]。该反应在神经组织和肝脏细胞中发生[6]。 5-羟色氨酸可以穿过血脑屏障[7],但5-羟色胺不能。过量的5-羟色氨酸会被代谢排出体外,特别是体内存在维生素B6时。[8][9]

5-HTP {{{forward_enzyme}}} 血清素
5-Hydroxy-L-Tryptophan (5-HTP).svg   Serotonin (5-HT).svg
{{{minor_forward_substrate(s)}}} {{{minor_forward_product(s)}}}
Biochem reaction arrow forward NNNN horiz med.svg
 
 

药理学[编辑]

5-羟色氨酸对中枢神经系统的作用在于其增加了血清素的生产[10]

Metabolic pathway from tryptophan to serotonin.

另见[编辑]

参考文献[编辑]

  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. PMID 15893130. doi:10.1016/j.mehy.2005.01.026. 
  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 C. Shaw, Kelly A, 编. Tryptophan and 5-hydroxytryptophan for depression. Cochrane Database of Systematic Reviews (Online). 2002, (1): CD003198. PMID 11869656. doi:10.1002/14651858.CD003198. 
  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. PMID 6983619. doi:10.1254/jjp.32.803. 
  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. PMID 6974228. doi:10.1111/j.1471-4159.1982.tb12555.x. 
  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. PMID 18445233. doi:10.1016/S0006-8993(99)01387-6. 
  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. PMID 39668. doi:10.1139/o79-126. 
  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]. (原始内容存档于2009-11-16). 

进一步阅读[编辑]

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