5-羟色氨酸

5-羟色氨酸
	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	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（英語：5-Hydroxytryptophan, 5-HTP；INN商品名：oxitriptan）是一种天然的氨基酸代谢中间产物，同时也是神经递质血清素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

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]。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]，但血清素不能。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

	{{{minor_forward_substrate(s)}}}	{{{minor_forward_product(s)}}}

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

^ ^1.0 ^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）.
^ Swiss Pharmaceutical Society. Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. 2000. ISBN 3-88763-075-0.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 5-HTP: Uses, Side Effects, Interactions and Warnings - WebMD. [2009-10-05]. （原始内容存档于2009-11-16）.

延伸阅读

den Boer JA, Westenberg HG. Behavioral, neuroendocrine, and biochemical effects of 5-hydroxytryptophan administration in panic disorder. Psychiatry Research. 1990, 31 (3): 267–78. PMID 2139731. doi:10.1016/0165-1781(90)90096-N.
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（英语：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. PMID 16023217. doi:10.1016/j.pharmthera.2005.06.004.
5-Hydroxytryptophan (5-HTP) Supplement Information（页面存档备份，存于互联网档案馆） at University of Maryland（英语：University of Maryland, Baltimore） Medical Center

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[pmid15893130-1] 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）.

[isbn3-88763-075-0-2] Swiss Pharmaceutical Society. Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. 2000. ISBN 3-88763-075-0.

[pmid11687048-3] 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] 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）.

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