I8250
3-Iodo-L-tyrosine
Tyrosine hydroxylase inhibitor
Synonym(s):
3-Monoiodo-L-tyrosine
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About This Item
Linear Formula:
IC6H3-4-(OH)CH2CH(NH2)CO2H
CAS Number:
Molecular Weight:
307.09
NACRES:
NA.32
PubChem Substance ID:
eCl@ss:
32160406
UNSPSC Code:
12352200
EC Number:
200-744-8
MDL number:
Beilstein/REAXYS Number:
2941266
Product Name
3-Iodo-L-tyrosine,
Quality Level
impurities
~5% tyrosine
mp
210 °C (dec.) (lit.)
solubility
dilute aqueous acid: soluble
storage temp.
−20°C
SMILES string
N[C@@H](Cc1ccc(O)c(I)c1)C(O)=O
InChI
1S/C9H10INO3/c10-6-3-5(1-2-8(6)12)4-7(11)9(13)14/h1-3,7,12H,4,11H2,(H,13,14)/t7-/m0/s1
InChI key
UQTZMGFTRHFAAM-ZETCQYMHSA-N
Gene Information
human ... TH(7054)
General description
Iodotyrosine coupled with di-iodotyrosine results in the synthesis of 3,5,3′-tri-iodothyronine (T3) or 3,3′,5′-tri-iodothyronine (rT3).
Application
3-Iodo-L-tyrosine has been used as an inhibitor for tyrosine hydroxylase enzyme in Drosophila and silkworm pupae.
Biochem/physiol Actions
3-iodotyrosine (3-IY) inhibits tyrosine hydroxylase that catalyzes levodopa (L-DOPA) formation from tyrosine. Iodotyrosine deiodinase enzyme deficiency leads to elevated levels of 3-IY in serum and urine in severe hypothyroidism and goiter.
TH (tyrosine 3-hydroxylase) is responsible for catalyzing the first step of the noradrenergic biosynthesis pathway. Mutations in TH are associated with tyrosine hydroxylase deficiency, leading to conditions such as infantile parkinsonism and DOPA (dopamine)-responsive dystonia as well as encephalopathy with perinatal onset.
Tyrosine hydroxylase inhibitor.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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L G Harsing et al.
Neuroscience, 77(2), 419-429 (1997-03-01)
Striatal slices from the rat were preincubated with [3H]GABA and superfused in the presence of nipecotic acid and aminooxyacetic acid, inhibitors of high-affinity GABA transport and GABA aminotransferase, respectively. GABA efflux was estimated by monitoring tritium efflux, 98% of which
D K Ness et al.
Fundamental and applied toxicology : official journal of the Society of Toxicology, 30(2), 153-161 (1996-04-01)
Planarians (Dugesia dorotocephala) were evaluated as bioassay organisms to detect inhibition of tyrosine hydroxylase, the rate-limiting enzyme in the synthesis of catecholamines. Thirty planaria per dose were exposed to 0 (control), 0.001, 0.01, 0.1, or 1 mM 3-iodo-L-tyrosine (monoiodotyrosine or
Differential regulation of tyrosine hydroxylase in cuticular melanization and innate immunity in the silkworm Bombyx mori
Lee KS, et al.
Journal of Asia-Pacific Entomology, 18(4), 765-770 (2015)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| I8250-1G | 04061833858493 |
| I8250-25G | 04061833858509 |
| I8250-5G | 04061833621110 |