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56-69-9 分子结构
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(2S)-2-amino-3-(5-hydroxyindol-3-yl)propanoic acid

ChemBase编号:2668
分子式:C11H12N2O3
平均质量:220.22458
单一同位素质量:220.08479225
SMILES和InChIs

SMILES:
N[C@@H](Cc1c[nH]c2ccc(O)cc12)C(=O)O
Canonical SMILES:
OC(=O)[C@H](Cc1c[nH]c2c1cc(O)cc2)N
InChI:
InChI=1S/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-VIFPVBQESA-N

引用这个纪录

CBID:2668 http://www.chembase.cn/molecule-2668.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
(2S)-2-amino-3-(5-hydroxyindol-3-yl)propanoic acid
(2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
IUPAC传统名
hydroxytryptophan
tryptophan, 5-hydroxy-, DL-
5-hydroxytryptophan
5-hydroxy-L-tryptophan
(2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
别名
5-羟基-L-色氨酸
L-5-羟基色氨酸水合物
5-Hydroxytryptophan
(S)-5-Hydroxytryptophan
5-Hydroxyl-L-tryptophan
5-Hydroxytryptophan
Cincofarm
Levothym
Levotinine
Oxitriptan
Oxyfan
Pretonine
Quietim
Serotonyl
Telesol
Tript-Oh
Triptene
5-Hydroxy L-Tryptophan
5-Hydroxy-L-Tryptophan
L-2-Amino-3-(5-hydroxyindolyl)propionic acid
5-Hydroxy-L-tryptophan
L-5-HTP
L-5-Hydroxytryptophan
L-2-Amino-3-[3-(5-hydroxyindole)]propionic acid
5-HTP
L-5-Hydroxytryptophan hydrate
Oxitriptan
CAS号
56-69-9
4350-09-8
EC号
224-411-1
MDL号
MFCD00064341
Beilstein号
88200
默克索引号
144847
PubChem SID
160966117
24278131
24846778
24880254
PubChem CID
439280
144
CHEBI ID
17780
ATC码
N06AX01
CHEMBL
350221
Chemspider ID
388413
KEGG ID
D07339
医学主题词(MeSH)
5-Hydroxytryptophan
美国药典/FDA物质标识码
C1LJO185Q9
维基百科标题
5-Hydroxytryptophan

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 2.152664  质子受体
质子供体 LogD (pH = 5.5) -1.3896201 
LogD (pH = 7.4) -1.3962954  Log P -1.3896985 
摩尔折射率 58.1837 cm3 极化性 23.689636 Å3
极化表面积 99.34 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P -1.56  LOG S -1.78 
溶解度 3.63e+00 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
DMSO expand 查看数据来源
Methanol expand 查看数据来源
外观
Off-White Solid expand 查看数据来源
powder expand 查看数据来源
熔点
~275 °C (dec.) expand 查看数据来源
222-224°C (dec.) expand 查看数据来源
258°C dec. expand 查看数据来源
270 °C (dec.)(lit.) expand 查看数据来源
270°C (dec.) expand 查看数据来源
298 - 300°C expand 查看数据来源
沸点
520.6°C expand 查看数据来源
密度
0.902 g/mL at 25 °C(lit.) expand 查看数据来源
1.484 g/mL expand 查看数据来源
折射率
n20/D 1.4850(lit.) expand 查看数据来源
比旋光度
[α]20/D -33±2°, c = 1% in H2O expand 查看数据来源
[α]22/D -30°, c = 1 in H2O expand 查看数据来源
-33 (c=1 in water) expand 查看数据来源
保存条件
2-8°C expand 查看数据来源
Refrigerator expand 查看数据来源
保存注意事项
IRRITANT expand 查看数据来源
RTECS编号
YN7110000 expand 查看数据来源
欧盟危险性物质标志
X expand 查看数据来源
有害性(Harmful) 有害性(Harmful) (Xn) expand 查看数据来源
联合国危险货物编号
2811 expand 查看数据来源
UN2811 expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
联合国危险货物等级
6.1 expand 查看数据来源
联合国危险货物包装类别(PG)
3 expand 查看数据来源
III expand 查看数据来源
危险公开号
22 expand 查看数据来源
22-36/37/38 expand 查看数据来源
R:22-36/37/38 expand 查看数据来源
安全公开号
26 expand 查看数据来源
36 expand 查看数据来源
S:25-26-36/37/39 expand 查看数据来源
TSCA收录
false expand 查看数据来源
expand 查看数据来源
GHS危险品标识
GHS06 expand 查看数据来源
GHS07 expand 查看数据来源
GHS警示词
Danger expand 查看数据来源
GHS危险声明
H301-H315-H319-H335 expand 查看数据来源
H302 expand 查看数据来源
GHS警示性声明
P261-P301 + P310-P305 + P351 + P338 expand 查看数据来源
P264-P270-P301+P312-P330-P501A expand 查看数据来源
个人保护装置
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand 查看数据来源
RID/ADR
UN 2811 6.1/PG 3 expand 查看数据来源
保存温度
2-8°C expand 查看数据来源
相关基因信息
human ... HTR1A(3350), HTR1B(3351), HTR1D(3352), HTR1E(3354), HTR1F(3355), HTR2A(3356), HTR2B(3357), HTR2C(3358), HTR3A(3359), HTR3B(9177), HTR3C(170572), HTR3D(200909), HTR3E(285242), HTR4(3360), HTR5A(3361), HTR5B(645694), HTR6(3362), HTR7(3363) expand 查看数据来源
生物活性机理
Precusor of 5-hydroxytryptamine expand 查看数据来源
纯度
≥99.0% (calc. based on dry substance, NT) expand 查看数据来源
95+% expand 查看数据来源
98% expand 查看数据来源
99% expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
燃烧残渣
≤0.05% expand 查看数据来源
生物来源
Metab. of Chromobacterium violaceum, constit. of the seeds of Griffonia simplicifolia. Occurs in large amts. in Panaeolus sphinctrinus and other Panaeolus spp. expand 查看数据来源
干燥失重
≤2% loss on drying expand 查看数据来源
应用领域
Antidepressant expand 查看数据来源
Psychostimulant expand 查看数据来源
Empirical Formula (Hill Notation)
C11H12N2O3 expand 查看数据来源

详细说明

详细说明

MP Biomedicals MP Biomedicals DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals -  05224995 external link
MP Biomedicals Rare Chemical collection
MP Biomedicals -  02100751 external link
Purity: 99%
Crystalline
Precursor of serotonin
DrugBank -  DB02959 external link
Item Information
Drug Groups experimental
Description 5-Hydroxytryptophan (5-HTP), also known as oxitriptan (INN), is a naturally occurring amino acid and chemical precursor as well as a metabolic intermediate in the biosynthesis of the neurotransmitters serotonin and melatonin from tryptophan. 5-HTP is sold over-the-counter in the United Kingdom, United States and Canada as a dietary supplement for use as an antidepressant, appetite suppressant, and sleep aid, and is also marketed in many European countries for the indication of major depression under trade names like Cincofarm, Levothym, Levotonine, Oxyfan, Telesol, Tript-OH, and Triptum. Several double-blind placebo-controlled clinical trials have demonstrated the effectiveness of 5-HTP in the treatment of depression, though a lack of high quality studies has been noted. More and larger studies are needed to determine if 5-HTP is truly effective in treating depression.
Indication For use as an antidepressant, appetite suppressant, and sleep aid.
Pharmacology The psychoactive action of 5-HTP is derived from its effect on the production of serotonin in central nervous system tissue. More specifically, 5-HTP increases the production of serotonin.
Affected Organisms
Humans and other mammals
Biotransformation 5-Hydroxytryptophan is decarboxylated to serotonin (5-hydroxytryptamine or 5-HT) by the enzyme aromatic-L-amino-acid decarboxylase with the help of vitamin B6. This reaction occurs both in nervous tissue and in the liver.
References
Turner EH, Blackwell AD: 5-Hydroxytryptophan plus SSRIs for interferon-induced depression: synergistic mechanisms for normalizing synaptic serotonin. Med Hypotheses. 2005;65(1):138-44. [Pubmed]
Shaw K, Turner J, Del Mar C: Tryptophan and 5-hydroxytryptophan for depression. Cochrane Database Syst Rev. 2002;(1):CD003198. [Pubmed]
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 Oct;32(5):803-11. [Pubmed]
Nakatani Y, Sato-Suzuki I, Tsujino N, Nakasato A, Seki Y, Fumoto M, Arita H: Augmented brain 5-HT crosses the blood-brain barrier through the 5-HT transporter in rat. Eur J Neurosci. 2008 May;27(9):2466-72. [Pubmed]
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 Jul;57(7):1014-8. [Pubmed]
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 Sep;25(2-3):135-40. [Pubmed]
Magnussen I, Jensen TS, Rand JH, Van Woert MH: Plasma accumulation of metabolism of orally administered single dose L-5-hydroxytryptophan in man. Acta Pharmacol Toxicol (Copenh). 1981 Sep;49(3):184-9. [Pubmed]
Birdsall TC: 5-Hydroxytryptophan: a clinically-effective serotonin precursor. Altern Med Rev. 1998 Aug;3(4):271-80. [Pubmed]
Sternberg EM, Van Woert MH, Young SN, Magnussen I, Baker H, Gauthier S, Osterland CK: Development of a scleroderma-like illness during therapy with L-5-hydroxytryptophan and carbidopa. N Engl J Med. 1980 Oct 2;303(14):782-7. [Pubmed]
Caruso I, Sarzi Puttini P, Cazzola M, Azzolini V: Double-blind study of 5-hydroxytryptophan versus placebo in the treatment of primary fibromyalgia syndrome. J Int Med Res. 1990 May-Jun;18(3):201-9. [Pubmed]
Trouillas P, Serratrice G, Laplane D, Rascol A, Augustin P, Barroche G, Clanet M, Degos CF, Desnuelle C, Dumas R, et al.: Levorotatory form of 5-hydroxytryptophan in Friedreich's ataxia. Results of a double-blind drug-placebo cooperative study. Arch Neurol. 1995 May;52(5):456-60. [Pubmed]
Birdsall TC: 5-Hydroxytryptophan: a clinically-effective serotonin precursor. Altern Med Rev. 1998 Aug;3(4):271-80. [Pubmed]
De Benedittis G, Massei R: Serotonin precursors in chronic primary headache. A double-blind cross-over study with L-5-hydroxytryptophan vs. placebo. J Neurosurg Sci. 1985 Jul-Sep;29(3):239-48. [Pubmed]
External Links
Wikipedia
Sigma Aldrich -  H9772 external link
Biochem/physiol Actions
Immediate precursor of serotonin; L-aromatic amino acid decarboxylase substrate.
Caution
Light sensitive
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H9772.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Sigma Aldrich -  107751 external link
包装
1 g in glass bottle
Sigma Aldrich -  56570 external link
Other Notes
芳香族 L-氨基酸脱羧酶试验的优选底物1
Toronto Research Chemicals -  H975710 external link
5-Hydroxy-L-Tryptophan is a hydroxylated metabolite of L-Tryptophan (T947210).

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Turner EH, Blackwell AD: 5-Hydroxytryptophan plus SSRIs for interferon-induced depression: synergistic mechanisms for normalizing synaptic serotonin. Med Hypotheses. 2005;65(1):138-44. Pubmed
  • Shaw K, Turner J, Del Mar C: Tryptophan and 5-hydroxytryptophan for depression. Cochrane Database Syst Rev. 2002;(1):CD003198. Pubmed
  • 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 Oct;32(5):803-11. Pubmed
  • Nakatani Y, Sato-Suzuki I, Tsujino N, Nakasato A, Seki Y, Fumoto M, Arita H: Augmented brain 5-HT crosses the blood-brain barrier through the 5-HT transporter in rat. Eur J Neurosci. 2008 May;27(9):2466-72. Pubmed
  • 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 Jul;57(7):1014-8. Pubmed
  • 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 Sep;25(2-3):135-40. Pubmed
  • Magnussen I, Jensen TS, Rand JH, Van Woert MH: Plasma accumulation of metabolism of orally administered single dose L-5-hydroxytryptophan in man. Acta Pharmacol Toxicol (Copenh). 1981 Sep;49(3):184-9. Pubmed
  • Birdsall TC: 5-Hydroxytryptophan: a clinically-effective serotonin precursor. Altern Med Rev. 1998 Aug;3(4):271-80. Pubmed
  • Sternberg EM, Van Woert MH, Young SN, Magnussen I, Baker H, Gauthier S, Osterland CK: Development of a scleroderma-like illness during therapy with L-5-hydroxytryptophan and carbidopa. N Engl J Med. 1980 Oct 2;303(14):782-7. Pubmed
  • Caruso I, Sarzi Puttini P, Cazzola M, Azzolini V: Double-blind study of 5-hydroxytryptophan versus placebo in the treatment of primary fibromyalgia syndrome. J Int Med Res. 1990 May-Jun;18(3):201-9. Pubmed
  • Trouillas P, Serratrice G, Laplane D, Rascol A, Augustin P, Barroche G, Clanet M, Degos CF, Desnuelle C, Dumas R, et al.: Levorotatory form of 5-hydroxytryptophan in Friedreich's ataxia. Results of a double-blind drug-placebo cooperative study. Arch Neurol. 1995 May;52(5):456-60. Pubmed
  • Birdsall TC: 5-Hydroxytryptophan: a clinically-effective serotonin precursor. Altern Med Rev. 1998 Aug;3(4):271-80. Pubmed
  • De Benedittis G, Massei R: Serotonin precursors in chronic primary headache. A double-blind cross-over study with L-5-hydroxytryptophan vs. placebo. J Neurosurg Sci. 1985 Jul-Sep;29(3):239-48. Pubmed
  • Gartside, S., et al.: Eur. J. Pharmacol., 179, 103 (1990)
  • Gijsman, H., et al.: J. Clin. Psychopharmacol., 22, 183 (1990)
  • ; Schruers, K., et al.: Psychiatry Res., 113, 237 (1990)
  • Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 146B, (nmr)
  • Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 673C; 673D, (ir)
  • Witkop, B. et al., J.A.C.S., 1954, 76, 5579, (synth)
  • Morris, A.J. et al., J.O.C., 1957, 22, 306, (resoln, abs config)
  • Biochem. Prep., 1962, 9, 92, (synth)
  • Tyler, V.E. et al., J. Pharm. Sci., 1964, 53, 462, (isol)
  • Bell, E.A. et al., Nature (London), 1966, 210, 529, (isol)
  • Wakahara, A. et al., Bull. Chem. Soc. Jpn., 1973, 46, 2475, (cryst struct)
  • Frahn, J.L. et al., Aust. J. Chem., 1974, 27, 1367, (synth, deriv)
  • Iriuchijima, S. et al., Agric. Biol. Chem., 1978, 42, 843, (synth, deriv)
  • Francis, P. et al., Biomed. Mass Spectrom., 1980, 7, 294, (ms, deriv)
  • Van Praag, H.M., Neuropharmacology, 1983, 22, 433, (rev)
  • Irie, K. et al., Chem. Pharm. Bull., 1984, 32, 2126, (synth)
  • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, HOA575; HOA600; HON800; HOO000; HOO100
  • For routes to 2-bromo-5-hydroxytryptophan derivatives, see: Synthesis, 28 (1996).
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