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D9503

Sigma-Aldrich

3,4-Dihydroxy-DL-phenylalanine

Synonym(s):

3-(3,4-Dihydroxyphenyl)-DL-alanine, DL-3-Hydroxytyrosine, DL-DOPA

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About This Item

Linear Formula:
(HO)2C6H3CH2CH(NH2)COOH
CAS Number:
63-84-3
Molecular Weight:
197.19
Beilstein:
3204800
EC Number:
200-566-0
MDL number:
MFCD00063060
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
24894298
NACRES:
NA.32

form

powder

mp

270-272 °C (lit.)
290 °C (dec.) (lit.)

SMILES string

NC(Cc1ccc(O)c(O)c1)C(O)=O

InChI

1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)

InChI key

WTDRDQBEARUVNC-UHFFFAOYSA-N

Gene Information

human ... DRD1(1812) , DRD2(1813) , DRD3(1814) , DRD4(1815) , DRD5(1816)
mouse ... DRD1(13488) , DRD2(13489) , DRD3(13490) , DRD4(13491) , DRD5(13492)
rat ... DRD1(24316) , DRD2(24318) , DRD3(29238) , DRD4(25432) , DRD5(25195)

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Biochem/physiol Actions

3,4-dihydroxyphenylalanine is an immediate precursor of dopamine, which is a product of tyrosine hydroxylase.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Steven L Saville et al.
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It has been recently reported that for some suspensions of magnetic nanoparticles the transverse proton relaxation rate, R(2), is dependent on the time that the sample is exposed to an applied magnetic field. This time dependence has been linked to
Handbook of Developmental Cognitive Neuroscience (2001)
Dopamine formation, from its immediate precursor 3, 4-dihydroxyphenylalanine, along the rat digestive tract
Vieira-Coelho MA and Soares-da-Silva P
Fundamental & Clinical Pharmacology, 7(5), 235-243 (1993)
Karlo J Lizarraga et al.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine, 55(1), 30-36 (2013-10-30)
Brain metastases are frequently treated with radiation. It is critical to distinguish recurrent or progressive brain metastases (RPBM) from late or delayed radiation injury (LDRI). The purpose of this study was to examine the diagnostic accuracy as well as the
Lionel C Libert et al.
Journal of nuclear medicine : official publication, Society of Nuclear Medicine, 54(7), 1154-1161 (2013-05-10)
6-(18)F-fluoro-L-dopa ((18)F-FDOPA) has proven to be a useful radiopharmaceutical for the evaluation of presynaptic dopaminergic function using PET. In comparison to electrophilic synthesis, the no-carrier-added (NCA) nucleophilic method has several advantages. These include much higher available activity and specific activity.
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