6-FLUORO-DL-TRYPTOPHAN
- CAS NO.:7730-20-3
- Empirical Formula: C11H11FN2O2
- Molecular Weight: 222.22
- MDL number: MFCD00005653
- EINECS: 231-788-6
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-19 20:33:22
What is 6-FLUORO-DL-TRYPTOPHAN?
Chemical properties
almost white to beige powder
What are the applications of Application
6-Fluoro-DL-tryptophan is a serotonin (5-HT) synthesis inhibitor
Definition
ChEBI: 6-Fluoro-DL-tryptophan is an indolyl carboxylic acid.
Biological Activity
6-fluoro-dl-tryptophan is a serotonin (5-ht) synthesis inhibitor.serotonin or 5-hydroxytryptamine (5-ht), a monoamine neurotransmitter, is biochemically derived from tryptophan. serotonin is primarily present in the gastrointestinal tract, blood platelets, and the central nervous system of animals. serotonin is considered to be a contributor to feelings of well-being and happiness.
in vitro
the potential competition was investigated between l-tryptophan (trp) and 6-fluoro-dl-tryptophan (6-f-trp). in equilibrium dialysis experiments, albumin bound about 80% of trp and 50% of 6-f-trp. competitive inhibition was assessed as the decrease in the apparent ka of trp in the presence of 6-f-trp, with no modification of the n value [1].
in vivo
rats werer administered 6-fluoro-dl-tryptophan (6f-trp) and its neurochemical effects on central catechole and indole were evaluated. results showed that neither norepinephrine nor dopamine and its major metabolites were affected by 6f-trp. with regard to serotonin (5-ht), 6f-trp could induce a transient depletion in all the studied brain areas, with a maximum of about 60-65% obtained between 1 and 3 hr. after 6 hr, 5-ht levels returned to control values. in addition, the 5-hydroxyindolacetic acid (5-hiaa) level was also reduced 3 hr after 6f-trp administration. a large dose-dependent increase in tryptophan was seen in the four brain areas, mainly due to an inhibition of tryptophan incorporation into protein, as demonstrated by experiments with mouse neuroblastoma cells [2].
References
[1] chanut, e. ,zini, r.,trouvin, j.h., et al. albumin binding and brain uptake of 6-fluoro-dl-tryptophan: competition with l-tryptophan. biochemical pharmacology 44(10), 2082-2085 (1992).
[2] chanut, e. ,trouvin, j.h.,bondoux, d., et al. metabolism of 6-fluoro-dl-tryptophan and its specific effects on the rat brain serotoninergic pathway. biochemical pharmacology 45(5), 1049-1057 (1992).
Properties of 6-FLUORO-DL-TRYPTOPHAN
Melting point: | 280-285 °C (dec.)(lit.) |
Boiling point: | 450.7±45.0 °C(Predicted) |
Density | 1.2556 (estimate) |
storage temp. | Keep in dark place,Inert atmosphere,Store in freezer, under -20°C |
solubility | Aqueous Base (Slightly), Methanol (Slightly, Heated), Water (Slightly) |
pka | 2.22±0.10(Predicted) |
form | crystalline |
color | Almost white to beige |
CAS DataBase Reference | 7730-20-3(CAS DataBase Reference) |
Safety information for 6-FLUORO-DL-TRYPTOPHAN
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. |
Computed Descriptors for 6-FLUORO-DL-TRYPTOPHAN
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