| Identification | Back Directory | [Name]
D-2-AMINO-3-(5-HYDROXYINDOLYL)PROPIONIC ACID | [CAS]
4350-07-6 | [Synonyms]
D-5-HTP
D-5-HYDROXYTRYPTOPHAN
5-hydroxy-d-tryptopha
D-Tryptophan, 5-hydroxy-
D-2-AMINO-3-(5-HYDROXYINDOLYL)PROPIONIC ACID
(R)-2-Amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
(2R)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
(2R)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propionic acid
(2R)-2-azanyl-3-(5-hydroxy-1H-indol-3-yl)propanoic acid | [Molecular Formula]
C11H12N2O3 | [MDL Number]
MFCD00069709 | [MOL File]
4350-07-6.mol | [Molecular Weight]
220.22 |
| Chemical Properties | Back Directory | [Melting point ]
270C | [Boiling point ]
520.6±50.0 °C(Predicted) | [density ]
1.484±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [pka]
2.22±0.10(Predicted) |
| Hazard Information | Back Directory | [Uses]
D-5-Hydroxytryptophan (D-5-HTP) is the D-isomer of 5-HTP and can be isolated from DL-5-hydroxytryptophan by continuous separation. Compared with intraperitoneal administration of L-5-Hydroxytryptophan, which can induce dose-dependent backward walking behavior in mice, D-5-Hydroxytryptophan has no significant effect on mouse behavior and is a negative control. D-5-Hydroxytryptophan is also a 5-HT ligand, capable of binding to the 5-HT site with affinity in the micromolar range[1][2][3]. | [Definition]
ChEBI: The D-enantiomer of 5-hydroxytryptophan. | [in vivo]
D-5-Hydroxytryptophan (100, 320 mg/kg; ip; single dose) cannot induce backward walking behavior in mice, while L-5-Hydroxytryptophan can do it[3].
| [References]
[1] J Arendt, et al. Alternative pathways of 5-hydroxyindole metabolism. II. The role transamination in the metabolism of D-5-hydroxytryptophan in the rat. Biochem Pharmacol. 1967 Mar;16(3):419-22. DOI:10.1016/0006-2952(67)90088-3
[2] Acton G. Effects of D-5-hydroxytryptophan and D-DOPA on binding at serotonin and dopamine receptors. Res Commun Chem Pathol Pharmacol. 1988 Apr;60(1):129-32. PMID:3132733
[3] Shimomura K, et al. Backward walking induced by L-5-hydroxytryptophan in mice. Jpn J Pharmacol. 1981 Feb;31(1):39-46. DOI:10.1254/jjp.31.39 |
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