3-Hydroxy-L-(2,5,6-2H3)tyrosine

Names

[ Name ]:
3-Hydroxy-L-(2,5,6-2H3)tyrosine

[Synonym ]:
L-DOPA-2,5,6-d3
L-Tyrosine-2,5,6-d, 3-hydroxy-
Dopa-phenyl-d3
MFCD00075014
L-Dihydroxyphenylalanine-2H3
3-Hydroxy-L-(2,5,6-H)tyrosine
2,3,6-trideuterio-4,5-dihydroxy-phenylalanine

Biological Activity

[Description]:

L-DOPA-2,5,6-d3 (Levodopa-2,5,6-d3) is the deuterium labeled L-DOPA. L-DOPA (Levodopa) is an orally active metabolic precursor of neurotransmitters dopamine. L-DOPA can cross the blood-brain barrier and is converted into dopamine in the brain[1][2][3].

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Dopamine Receptor

Signaling Pathways >> Neuronal Signaling >> Dopamine Receptor

Research Areas >> Neurological Disease

[In Vitro]

Stable heavy isotopes of hydrogen, carbon, and other elements have been incorporated into drug molecules, largely as tracers for quantitation during the drug development process. Deuteration has gained attention because of its potential to affect the pharmacokinetic and metabolic profiles of drugs[1].

[References]

[1]. Russak EM, et al. Impact of Deuterium Substitution on the Pharmacokinetics of Pharmaceuticals. Ann Pharmacother. 2019;53(2):211-216.

[2]. Hyland K, et al. Aromatic L-amino acid decarboxylase deficiency: diagnostic methodology. Clin Chem. 1992 Dec;38(12):2405-10.

[3]. Merims D, et al. Dopamine dysregulation syndrome, addiction and behavioral changes in Parkinson's disease. Parkinsonism Relat Disord. 2008;14(4):273-80. Epub 2007 Nov 7.

[4]. Perez-Pardo P, et al. Additive Effects of Levodopa and a Neurorestorative Diet in a Mouse Model of Parkinson's Disease. Front Aging Neurosci. 2018 Aug 3;10:237.

[5]. Park HJ, et al. Anti-allodynic effects of levodopa in neuropathic rats. Yonsei Med J. 2013 Mar 1;54(2):330-5.

Chemical & Physical Properties

[ Density]:
1.49g/cm3

[ Boiling Point ]:
448.4ºC at 760 mmHg

[ Melting Point ]:
292ºC (dec.)(lit.)

[ Molecular Formula ]:
C₉H₈D₃NO₄

[ Molecular Weight ]:
200.20600

[ Flash Point ]:
225ºC

[ Exact Mass ]:
200.08800

[ PSA ]:
103.78000

[ LogP ]:
0.75250

[ Index of Refraction ]:
1.654

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

Articles

Restriction of dopamine signaling to the dorsolateral striatum is sufficient for many cognitive behaviors.

Proc. Natl. Acad. Sci. U. S. A. 106(34) , 14664-9, (2009)

The striatum is a vital substrate for performance, procedural memory, and learning. The ventral and medial striatum are thought to be critical for acquisition of tasks while the dorsolateral striatum ...

Capsules from pathogenic and non-pathogenic Cryptococcus spp. manifest significant differences in structure and ability to protect against phagocytic cells.

PLoS ONE 7 , e29561, (2012)

Capsule production is common among bacterial species, but relatively rare in eukaryotic microorganisms. Members of the fungal Cryptococcus genus are known to produce capsules, which are major determin...