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Also known as: L-5-hydroxytryptophan, Oxitriptan, 4350-09-8, 5-hydroxytryptophan, Cincofarm, Levothym
Molecular Formula
C11H12N2O3
Molecular Weight
220.22  g/mol
InChI Key
LDCYZAJDBXYCGN-VIFPVBQESA-N
FDA UNII
C1LJO185Q9

5-Hydroxy Tryptophan
The immediate precursor in the biosynthesis of SEROTONIN from tryptophan. It is used as an antiepileptic and antidepressant.
1 2D Structure

5-Hydroxy Tryptophan

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
2.1.2 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
2.1.3 InChI Key
LDCYZAJDBXYCGN-VIFPVBQESA-N
2.1.4 Canonical SMILES
C1=CC2=C(C=C1O)C(=CN2)CC(C(=O)O)N
2.1.5 Isomeric SMILES
C1=CC2=C(C=C1O)C(=CN2)C[C@@H](C(=O)O)N
2.2 Other Identifiers
2.2.1 UNII
C1LJO185Q9
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 5 Hydroxytryptophan

2. 5-htp

3. 5-hydroxy- Tryptophan

4. 5-hydroxytryptophan

5. Hydroxytryptophan

6. Oxitriptan

7. Oxytryptophan

8. Tryptophan, 5 Hydroxy

9. Tryptophan, 5-hydroxy-

2.3.2 Depositor-Supplied Synonyms

1. L-5-hydroxytryptophan

2. Oxitriptan

3. 4350-09-8

4. 5-hydroxytryptophan

5. Cincofarm

6. Levothym

7. L-5-htp

8. Pretonine

9. Tryptophan, 5-hydroxy-

10. Quietim

11. 5-hydroxytryptophan L-form

12. Oxyfan

13. Hydroxytryptophan

14. (2s)-2-amino-3-(5-hydroxy-1h-indol-3-yl)propanoic Acid

15. Levotinine

16. Serotonyl

17. Triptene

18. Telesol

19. Tript-oh

20. (s)-2-amino-3-(5-hydroxy-1h-indol-3-yl)propanoic Acid

21. Oxitriptan [inn]

22. L-tryptophan, 5-hydroxy-

23. 5-htp

24. 5-hydroxyl-l-tryptophan

25. (s)-5-hydroxytryptophan

26. H-trp(5-oh)-oh

27. C1ljo185q9

28. Ro 3-5940 Hcl

29. Chebi:17780

30. Oxitriptan (inn)

31. Ncgc00091062-04

32. L-2-amino-3-(5-hydroxyindolyl)propionic Acid

33. Mfcd00064341

34. Dsstox_cid_5437

35. Dsstox_rid_77786

36. Dsstox_gsid_25437

37. Dl-oxitriptan

38. Tryptophan, 5-hydroxy-, L-

39. 5-hydroxy-l-tryptophane

40. 5-hydroxy Tryptophan

41. (s)-2-amino-3-(5-hydroxy-1h-indol-3-yl)propanoic Acid (5-hydroxytryptophan)

42. 5 Hydroxytryptophan

43. Cas-4350-09-8

44. 5-hydroxytryptophan, Dl-

45. 5-hydroxytryptophan L Form

46. Tryptophan, 5-hydroxy-, Dl

47. 5-22-14-00278 (beilstein Handbook Reference)

48. Oxitriptanum [inn-latin]

49. Oxitriptano [inn-spanish]

50. Oxitriptano

51. Oxitriptanum

52. Serotain

53. Tripten

54. L-oxitriptan

55. Ccris 4418

56. Levothym (tn)

57. Einecs 224-411-1

58. 5-hydroxytryptophane

59. Tryptophan, 5-htp

60. Brn 0088200

61. 5htp

62. Lopac-h-9772

63. Bmse000457

64. L-5-http

65. Oxitriptan [mart.]

66. 5-hydroxy-tryptophan

67. Oxitriptan [who-dd]

68. Unii-c1ljo185q9

69. Lopac0_000627

70. Schembl43243

71. Mls002153452

72. 5-hydroxytryptophan - 5-htp

73. (2s)-2-amino-3-(5-hydroxyindol-3-yl)propanoic Acid

74. 5-hydroxy L-tryptophan-[d4]

75. Chembl350221

76. Gtpl4671

77. 5-hydroxy-l-tryptophan, Powder

78. Hydroxytryptophan [inci]

79. Dtxsid1025437

80. Hydroxytryptophan [vandf]

81. Hms2231h15

82. Hms3261n16

83. Zinc895330

84. Hy-b1716

85. Tox21_111073

86. Tox21_201032

87. Tox21_500627

88. Bdbm50403163

89. Oxitriptan (5-hydroxy-l-tryptophan)

90. S4769

91. Akos004119863

92. Tox21_111073_1

93. Ccg-204715

94. Cs-w019879

95. Db02959

96. Lp00627

97. Sdccgsbi-0050608.p002

98. 5-hydroxy-l-tryptophan [usp-rs]

99. 5-hydroxytryptophan L-form [mi]

100. Ncgc00015526-01

101. Ncgc00091062-01

102. Ncgc00091062-02

103. Ncgc00091062-03

104. Ncgc00091062-05

105. Ncgc00091062-06

106. Ncgc00091062-07

107. Ncgc00091062-08

108. Ncgc00091062-09

109. Ncgc00091062-12

110. Ncgc00258585-01

111. Ncgc00261312-01

112. Ac-24420

113. As-12269

114. Smr001230815

115. Tryptophan Impurity D [ep Impurity]

116. Am20060629

117. Eu-0100627

118. H0531

119. 50h098

120. C00643

121. D07339

122. H 9772

123. L-5-hydroxytryptophan (l-5-htp; Oxitriptan)

124. A826297

125. Q238544

126. Sr-01000075584

127. N-acetyltryptophan Impurity D [ep Impurity]

128. Q-200544

129. Sr-01000075584-1

130. 2-amino-3-(5-hydroxy-1h-indol-3-yl)propionic Acid

131. S(+)-1-alpha-amino-5-hydroxyindole-3-propionic Acid

132. 5-hydroxy-l-tryptophan, 98% (calc. On Dried Substance)

133. Cdad59d9-d915-46dd-8029-48c808976b7c

134. 5-hydroxy-l-tryptophan, United States Pharmacopeia (usp) Reference Standard

135. 4pq

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 220.22 g/mol
Molecular Formula C11H12N2O3
XLogP3-1.2
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count4
Rotatable Bond Count3
Exact Mass220.08479225 g/mol
Monoisotopic Mass220.08479225 g/mol
Topological Polar Surface Area99.3 Ų
Heavy Atom Count16
Formal Charge0
Complexity272
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

5-HTP has shown some usefulness in some conditions characterized, in part, by serotonin deficits, principally depression. It has also been shown to be useful in some with obesity, insomnia, fibromyalgia and chronic tension headache.

Physicians Desk Reference (PDR) for Nutritional Supplements 1st ed, Medical Economics, Thomson Healthcare; Montvale, NJ p.4 (2001)


It has been long known that brain serotonin systems contribute to the modulation of food intake and satiety. An increase of intrasynaptic serotonin tends to reduce food consumption. Thus, one might consider that individuals taking 5-HTP might experience increase satiety and weight loss over a period of time. There are few studies on the effects of 5-HTP on obesity and they suggest an anorectic effect of 5-HTP.

Coates, P.M., Blackman, M.R., Cragg, G.M., Levine, M., Moss, J., White, J.D. (Ed), Encyclopedia of Dietary Supplements. Marcel Dekker, New York, NY, p. 350 (2005)


There is some evidence that 5-HTP ... can improve postural equilibrium, dysarthria in patients with various inherited and acquired cerebellar ataxias, and particularly in those with lesions located precisely in the anterior lobe vermis. Improvements in coordination have been reported in patients with Friedreich"s ataxia; however, the effect is only partial and not clinically major.

Coates, P.M., Blackman, M.R., Cragg, G.M., Levine, M., Moss, J., White, J.D. (Ed), Encyclopedia of Dietary Supplements. Marcel Dekker, New York, NY, p. 352 (2005)


Exptl Ther: Rats of the Dahl salt-sensitive (DS) and Dahl salt-resistant (DR) strains were placed on a 4% NaCl diet and blood pressures were monitored. Chronic subcutaneous infusion L-5-hydroxytryptophan (L-5-HTP, 12.6 mg/day) by osmotic minipumps significantly decreased the elevated systolic blood pressure of DS rats on a 4% NaCl diet. Blood pressures of DR rats were unaffected by treatment with L-5-HTP. Cardiac hypertrophy was associated with Dahl salt-induced hypertension. However, treatment with L-5-HTP failed to reduce the weight of the heart significantly. These results suggest that chronic administration of L-5-HTP was effective in reducing the elevated blood pressure in the DS model. The specific mechanisms by which L-5-HTP reduces the elevated blood pressure in DS rats is not clear and remains for further study.

PMID:1829234 Baron A et al; Pharmacology 42 (1): 15-22 (1991)


For more Therapeutic Uses (Complete) data for 5-HYDROXYTRYPTOPHAN (6 total), please visit the HSDB record page.


4.2 Drug Warning

Other reported side effects, include nausea, diarrhea, loss of appetite, vomiting and difficult breathing. Neurological side effects, including dilation of the pupils, abnormally sensitive reflexes, loss of muscle coordination and blurring of vision, have been reported in those taking large doses of 5-HTP. Cardiac dysrhythmias have also been reported.

Physicians Desk Reference (PDR) for Nutritional Supplements 1st ed, Medical Economics, Thomson Healthcare; Montvale, NJ p.5 (2001)


Eosinophilia and eosinophilia-myalgia syndrome (EMS) have been reported in those taking 5-HTP. The eosinophilia myalgia syndrome is similar to that caused by L-tryptophan and was linked to contaminants in the 5-HTP preparation, rather than 5-HTP itself. Changing the 5-HTP lot in one group of patients resolved the eosinophilia. A scleroderma-like skin condition has been reported in some taking a combination of 5-HTP and carbidopa.

Physicians Desk Reference (PDR) for Nutritional Supplements 1st ed, Medical Economics, Thomson Healthcare; Montvale, NJ p.5 (2001)


5-HTP should be avoided by pregnant women and nursing mothers.

Physicians Desk Reference (PDR) for Nutritional Supplements 1st ed, Medical Economics, Thomson Healthcare; Montvale, NJ p.5 (2001)


5-HTP should be avoided by those with ischemic heart disease (history of myocardial infarction, angina pectoris, documented silent ischemia), coronary artery spasm (e.g., Prinzmetal's angina), uncontrollable hypertension and any other significant cardiovascular disease.

Physicians Desk Reference (PDR) for Nutritional Supplements 1st ed, Medical Economics, Thomson Healthcare; Montvale, NJ p.4 (2001)


For more Drug Warnings (Complete) data for 5-HYDROXYTRYPTOPHAN (8 total), please visit the HSDB record page.


4.3 Drug Indication

For use as an antidepressant, appetite suppressant, and sleep aid.


5 Pharmacology and Biochemistry
5.1 Pharmacology

The psychoactive action of 5-HTP is thought to be due to increased serotonin production in central nervous system tissue.


5.2 MeSH Pharmacological Classification

Antidepressive Agents, Second-Generation

A structurally and mechanistically diverse group of drugs that are not tricyclics or monoamine oxidase inhibitors. The most clinically important appear to act selectively on serotonergic systems, especially by inhibiting serotonin reuptake. (See all compounds classified as Antidepressive Agents, Second-Generation.)


5.3 ATC Code

N - Nervous system

N06 - Psychoanaleptics

N06A - Antidepressants

N06AX - Other antidepressants

N06AX01 - Oxitriptan


5.4 Absorption, Distribution and Excretion

The immediate precursor in the serotonin synthetic route, 5-hydroxytryptophan (5-HTP), labeled with 11C in the beta position, has become available for studies using positron emission tomography (PET) to examine serotonin formation in human brain. Normalized uptake and intracerebral utilization of tracer amounts of (beta-11C)5-HTP were studied twice in six healthy male volunteers, three of them before and after pharmacological pretreatments ... Pretreatments with benserazide, p-chlorophenylalanine (PCPA), and unlabeled 5-HTP all significantly increased uptake of (beta-11C)5-HTP. The utilization rates in both striatal and frontal cortex were higher than those in the surrounding brain, indicating that PET studies using (beta-11C)5-HTP as a ligand quantitate selective processes in the utilization of 5-HTP.

PMID:1292039 Reibring L et al; Psychiatry Res 45(4): 215-25 (1992)


The efficiency of absorption of 5HTP, as well as its decarboxylation product serotonin, is approximately 47% to 84%. Absorption of 5-HTP occurs by an active transport process. 5-HTP is transported by the portal circulation to the liver where approximately 25% of an administered dose is metabolized ... . 5-HTP that is not metabolized in the liver is transported by the general circulation to the various tissues of the body, including the brain. 5-HTP readily crosses the blood-brain barrier, and is converted to serotonin in brain cells.

Physicians Desk Reference (PDR) for Nutritional Supplements 1st ed, Medical Economics, Thomson Healthcare; Montvale, NJ p.4 (2001)


5.5 Metabolism/Metabolites

5-Hydroxytryptophan is decarboxylated to serotonin (5-hydroxytryptamine or 5-HT) by the enzyme aromatic-L-amino-acid decarboxylase via a vitamin B6 dependent reaction in nervous tissue and in the liver.


5-HTP is transported by the portal circulation to the liver where approximately 25% of an administered dose is metabolized via vitamin B6-dependent L-aromatic amino acid decarboxylase to 5-hydroxytryptamine (5-HT) /serotonin/. 5-HT is subsequently metabolized to 5-hydroxyindole acetaldehyde which is rapidly metabolized to 5-hydroxyindole acetaldehyde which is rapidly metabolized to 5-hydroxyindoleacetic acid (5-HIAA).

Physicians Desk Reference (PDR) for Nutritional Supplements 1st ed, Medical Economics, Thomson Healthcare; Montvale, NJ p.4 (2001)


5.6 Mechanism of Action

The possible analgesic effect of 5-HTP may be accounted for, in part, by its conversion to serotonin. 5-HTP has also been found to increase plasma beta-endorphin and platelet met-enkephalin levels, which may signify a reinforcing effect upon an endogenous analgesic effect.

Physicians Desk Reference (PDR) for Nutritional Supplements 1st ed, Medical Economics, Thomson Healthcare; Montvale, NJ p.3 (2001)


The mechanism of the possible antidepressant activity of 5-HTP is accounted for by its conversion to the neurotransmitter serotonin which plays a central role in the affective state. Antidepressants may work by either binding to one or more of the family of serotonin 5-HT receptors (5-HT1 - 5-HT7) or by inhibiting the reuptake of serotonin. ...

Physicians Desk Reference (PDR) for Nutritional Supplements 1st ed, Medical Economics, Thomson Healthcare; Montvale, NJ p.3 (2001)


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