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
Ball-and-stick model
IUPAC名
2-amino-3- (5-hydroxy-1H-indol-3-yl) propanoic acid
识别
CAS号56-69-9
PubChem144
ChemSpider388413
SMILES
InChI
InChIKeyLDCYZAJDBXYCGN-VIFPVBQEBZ
ChEBI17780
KEGGD07339
MeSH5-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 )是一种天然的氨基酸代谢中间产物，同时也是神经递质5-羟色胺与褪黑素的生物合成前体。

5-羟色氨酸在美英以及加拿大以非处方药方式出售，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]。

目录

  1. 代谢
  2. 药理学
  3. 另见
  4. 参考文献
  5. 进一步阅读
  6. 参考来源

代谢

5-羟色氨酸由芳香族L-氨基酸脱羧酶在维生素B6帮助下脱羧为血清素(5-羟色胺，5-HT)[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-HTPAAAD血清素
5-Hydroxy-L-Tryptophan (5-HTP).svg Serotonin (5-HT).svg
磷酸吡哆醛
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药理学

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

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. 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] (原始内容存档於16 November 2009). 

进一步阅读

  • den Boer JA, Westenberg HG. Behavioral, neuroendocrine, and biochemical effects of 5-hydroxytryptophan administration in panic disorder. Psychiatry Research. 1990, 31 (3): 267–78. doi:10.1016/0165-1781(90)90096-N. PMID 2139731. 
  • Angst J, Woggon B, Schoepf J. The treatment of depression with L-5-hydroxytryptophan versus imipramine. Results of two open and one double-blind study. Archiv für Psychiatrie und Nervenkrankheiten. 1977, 224 (2): 175–86. PMID 336002. 
  • article at Psychology Today
  • Turner EH, Loftis JM, Blackwell AD. Serotonin a la carte: supplementation with the serotonin precursor 5-hydroxytryptophan. Pharmacol. Ther.. 2006, 109 (3): 325–38. doi:10.1016/j.pharmthera.2005.06.004. PMID 16023217. 
  • 5-Hydroxytryptophan (5-HTP) Supplement Information at University of Maryland Medical Center
(+) 5-HT1AR
(+) GABAAR
其它
(–) α2δ-VDCC
抗抑郁药
交感神经阻滞剂
其它
中枢
  • 屈那班
  • 伊必那班
  • Otenabant
  • 利莫那班
  • Rosonabant
  • 溴乙那班
  • 泰伦那班
其他
末稍

模板:Hypnotics

神经递质代谢中间产物
儿茶酚胺
合成代谢
(酪氨酸→肾上腺素)
代谢/
代谢产物
多巴胺:
  • DOPAL
  • DOPAC
  • MOPET
  • Hydroxytyrosol
  • 3-Methoxytyramine
  • Homovanillic acid
去甲肾上腺素:
  • 3,4-Dihydroxymandelic acid
  • Normetanephrine
  • Vanillylmandelic acid
  • 3-Methoxy-4-hydroxyphenylglycol
  • Dihydroxyphenylethylene glycol
肾上腺素:
  • Metanephrine
色氨酸→血清素
合成代谢:
  • 5-羟色氨酸
分解代谢:
  • 5-Hydroxyindoleacetic acid
血清素→褪黑素

模板:Serotonergics

色胺及其衍生物
直接衍生物
  • 5-羟色胺
  • 2-甲基-5-羟色胺
  • 色氨酸
  • 5-羟色氨酸
  • 4-HO-αMT
  • 4-Me-αET
  • 4-Me-αMT
  • 5-BT
  • 5-CT
  • 5-Ethoxy-αMT
  • 5-Fluoro-αMT
  • 5-HO-αMT
  • 5-Methoxytryptamine
  • 5-MeO-7,N,N-TMT
  • 5-Methyl-αET
  • 5-MeO-αET
  • 5-MeO-αMT
  • 5-MeO-MALT
  • 5-MeO-MiPT
  • 5,7-Dihydroxytryptamine
  • 5-(Nonyloxy)tryptamine
  • 6-Fluoro-αMT
  • 7-Methyl-αET
  • αET
  • αMT
  • AL-37350A
  • BW-723C86
  • 吲哚瑞酯
  • Norbaeocystin
氨基N-取代
衍生物
  • N-甲基色胺(NMT)
  • DPT
  • EiPT
  • EMDT
  • EPT
  • MET
  • MiPT
  • MPT
  • PiPT
  • 4,5-MDO-DiPT
  • 4-AcO-DET
  • 4-AcO-DiPT
  • 4-AcO-MET
  • 4-AcO-MiPT
  • 4-HO-DET
  • 4-HO-DiPT
  • 4-HO-DSBT
  • 4-HO-MET
  • 4-HO-MiPT
  • 5-MeO-DALT
  • 5-MeO-DET
  • 5-MeO-DiPT
  • 5-MeO-DPT
  • 5-MeO-NBpBrT
  • Aeruginascin
  • Baeocystin
  • DALT
  • Desformylflustrabromine
  • Ibogaine
  • Miprocin
  • FGIN-127
  • FGIN-143
  • N-乙酰血清素
  • 褪黑素
  • 育亨宾
  • 蟾蜍特尼定
氨基N,N-二取代
衍生物
  • DET
  • DiPT
  • 4-羟二乙基色胺
  • 4-磷酸二乙基色胺
  • 4-羟二异丙基色胺
  • 奥昔哌汀
N,N-二甲基色胺
(DMT)
及衍生物

参考来源