5-羟色氨酸

5-羟色氨酸
	IUPAC命名法; 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-羟基色氨酸（英語：5-Hydroxytryptophan，简称5-HTP），也称欧西曲坦（INN：oxitriptan），是一种天然的氨基酸代谢中间产物，化学式为C₁₁H₁₂N₂O₃，也是血清素（5-羟色胺）与褪黑素生物合成途径中的直接前体。^[1]5-HTP的CAS号为56-69-9，分子量为220.22。其在水中溶解度为4 mg/mL（25°C），在DMSO中溶解度为40 mg/mL，不溶于乙醇。

药理作用

5-HTP的药理作用核心在于其作为血清素前体的身份。与色氨酸不同，5-HTP能够直接穿透血脑屏障，在神经细胞末端经芳香族L-氨基酸脱羧酶（AAAD）催化，脱羧转化为血清素。这一过程需要磷酸吡哆醛（维生素B6）作为辅酶。此外，5-HTP也可在外周组织中转化为血清素，但中枢神经系统的转化是其发挥抗抑郁和调节睡眠等作用的关键。^[2]

临床应用

5-羟色氨酸作为给抑郁症、厌食症及失眠患者服用的膳食补充剂，在美国、英国和加拿大以非处方方式出售，也作为治疗重性抑郁障碍的药物在欧洲许多国家销售^[3]^[4]，有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^[3]，但缺乏极显著性^[5]，需要更进一步的临床对照研究^[6]。

代谢

在神经组织和肝细胞中^[7]，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）^[8]。 5-羟色氨酸可以穿过血脑屏障^[9]，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。^[10]^[11]

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^[12]。

不良反应

5-HTP的常见不良反应主要与胃肠道相关，包括恶心、呕吐、腹泻、腹痛和食欲减退，这些反应通常与剂量相关。其他可能的不良反应包括头痛、头晕、嗜睡或失眠、焦虑以及性功能障碍。需警惕的是血清素综合征，这是一种可能危及生命的状况，由中枢神经系统血清素水平过高引起，表现为高热、高血压、心动过速、肌肉痉挛、焦虑、意识模糊等症状。^[13]

另见

参考文献

^ Physician Data Query - oxitriptan - Classes | NCBO BioPortal. bioportal.bioontology.org. [2026-09-16].
^ L-5-Hydroxytryptophan(Oxitriptan). www.orphan-drug.org. [2026-09-16].
^ ^3.0 ^3.1 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.
^ 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.
^ 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.
^ 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）.
^ L-5-Hydroxytryptophan(Oxitriptan). www.orphan-drug.org. [2026-09-16].

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

[1] Physician Data Query - oxitriptan - Classes | NCBO BioPortal. bioportal.bioontology.org. [2026-09-16].

[2] L-5-Hydroxytryptophan(Oxitriptan). www.orphan-drug.org. [2026-09-16].

[pmid15893130-3] 3.0 ^3.1 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）.

[isbn3-88763-075-0-4] Swiss Pharmaceutical Society. Index Nominum 2000: International Drug Directory (Book with CD-ROM). Boca Raton: Medpharm Scientific Publishers. 2000. ISBN 3-88763-075-0.

[pmid11687048-5] 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.

[6] 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.

[7] 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.

[8] 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.

[9] 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.

[10] 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.

[11] 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.

[12] 5-HTP: Uses, Side Effects, Interactions and Warnings - WebMD. [2009-10-05]. （原始内容存档于2009-11-16）.

[13] L-5-Hydroxytryptophan(Oxitriptan). www.orphan-drug.org. [2026-09-16].

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