5-羥色氨酸

5-羥色氨酸
	IUPAC名; 2-amino-3- (5-hydroxy-1H-indol-3-yl) propanoic acid
識別
CAS號	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
ATC代碼	N06AX01
性質(zhì)
化學(xué)式	C11H12N2O3
摩爾質(zhì)量	220.23 g/mol g·mol?1
密度	1.484 g/mL
熔點(diǎn)	298-300 °C（571-573 K）
沸點(diǎn)	520.6 °C（794 K）
	若非注明，所有數(shù)據(jù)均出自一般條件（25 ℃，100 kPa）下。

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A+醫(yī)學(xué)百科 >> 5-羥色氨酸

提示：本條目的主題不是血清素 (5-羥色胺，5-HT)。

5-羥色氨酸(英語：5-Hydroxytryptophan，5-HTP)，(INN商品名：oxitriptan )是一種天然的氨基酸代謝中間產(chǎn)物，同時也是神經(jīng)遞質(zhì)5-羥色胺與褪黑素的生物合成前體。

5-羥色氨酸在美英以及加拿大以非處方藥方式出售，作為幫助抑郁癥、厭食癥及失眠患者的膳食補(bǔ)充劑，同時也作為治療重性抑郁障礙的藥物在歐洲許多國家銷售。^[1]^[2]幾個安慰劑雙盲臨床試驗(yàn)已證明5-HTP有治療抑郁癥的效果^[1]，但缺乏極顯著性^[3]，需要更進(jìn)一步的大量臨床對照研究^[4]。

代謝

5-羥色氨酸由芳香族L-氨基酸脫羧酶在維生素B6幫助下脫羧為血清素(5-羥色胺，5-HT)^[5]。該反應(yīng)在神經(jīng)組織和肝臟細(xì)胞中發(fā)生^[6]。 5-羥色氨酸可以穿過血腦屏障^[7]，但5-羥色胺不能。過量的5-羥色氨酸會被代謝排出體外，特別是體內(nèi)存在維生素B6時。^[8]^[9]

5-HTP	AAAD	血清素

	磷酸吡哆醛
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藥理學(xué)

5-羥色氨酸對中樞神經(jīng)系統(tǒng)的作用在于其增加了血清素的生產(chǎn)^[10]。

Metabolic pathway from tryptophan to serotonin.

另見

參考文獻(xiàn)

↑ ^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.
↑ 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 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.
↑ 5-Hydroxytryptophan (5-HTP) 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. doi:10.1254/jjp.32.803. PMID 6983619.
↑ 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.
↑ 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.
↑ 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.
↑ 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] (原始內(nèi)容存檔於16 November 2009).

進(jìn)一步閱讀

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

模板:Hypnotics

模板:Serotonergics

參考來源

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5-羥色氨酸

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另見

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進(jìn)一步閱讀

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5-羥色氨酸


IUPAC名 2-amino-3- (5-hydroxy-1H-indol-3-yl) propanoic acid
識別
CAS號	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
ATC代碼	N06AX01
性質(zhì)
化學(xué)式	C₁₁H₁₂N₂O₃
摩爾質(zhì)量	220.23 g/mol g·mol?1
密度	1.484 g/mL
熔點(diǎn)	298-300 °C（571-573 K）
沸點(diǎn)	520.6 °C（794 K）
若非注明，所有數(shù)據(jù)均出自一般條件（25 ℃，100 kPa）下。