5-羟色氨酸

5-羟色氨酸(英語:5-Hydroxytryptophan,简称5-HTP),也叫欧西曲坦(INN:oxitriptan),是一种天然氨基酸代谢中间产物,同时也是血清素褪黑素生物合成前体

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  checkY
PubChem 144
ChemSpider 388413
SMILES
 
  • O=C(O)[C@@H](N)Cc2c1cc(O)ccc1nc2
InChI
 
  • 1/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16)/t9-/m0/s1
InChIKey LDCYZAJDBXYCGN-VIFPVBQEBZ
ChEBI 17780
KEGG D07339
MeSH 5-Hydroxytryptophan
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,所有数据均出自标准状态(25 ℃,100 kPa)下。

5-羟色氨酸作为给抑郁症厌食症失眠患者服用的膳食补充剂,在美国英国加拿大非处方方式出售;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],需要更进一步的临床对照研究[4]

代谢

神经组织肝细胞[5],5-羟色氨酸在芳香族L-氨基酸脱羧酶维生素B6帮助下脱羧生成血清素(5-羟色胺)[6]。 5-羟色氨酸可以穿过血脑屏障[7],但血清素不能。过量的5-羟色氨酸会被代谢排出体外,体内的维生素B6会促进这种代谢。[8][9]

5-HTP AAAD 血清素
     
PLP
 
 
 


药理学

5-羟色氨酸可促进中枢神经系统分泌血清素[10]

 
Metabolic pathway from tryptophan to serotonin.

另见

参考文献

  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 [2013-08-14]. PMID 15893130. doi:10.1016/j.mehy.2005.01.026. (原始内容存档于2018-10-13). 
  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)页面存档备份,存于互联网档案馆University of Maryland Medical Center. 2011. Accessed: 9 January 2012.
  5. ^ 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. 
  6. ^ 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. 
  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). 

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