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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

Quality Level

100

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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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)
Handbook of Developmental Cognitive Neuroscience (2001)
Oliver D Howes et al.
Brain : a journal of neurology, 136(Pt 11), 3242-3251 (2013-10-08)
Elevated in vivo markers of presynaptic striatal dopamine activity have been a consistent finding in schizophrenia, and include a large effect size elevation in dopamine synthesis capacity. However, it is not known if the dopaminergic dysfunction is limited to the
Thorben Schlüter et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 33(43), 16889-16896 (2013-10-25)
Cerebral dopamine (DA) transmission is thought to be an important modulator for the development and occurrence of aggressive behavior. However, the link between aggression and DA transmission in humans has not been investigated using molecular imaging and standardized behavioral tasks.
Kyuri Lee et al.
International journal of pharmaceutics, 445(1-2), 196-202 (2013-01-19)
Calcium phosphate (CAP) has a wide range of applications in biomedical systems. Although there is great potential for the use of CAP in the development of gene delivery systems, the uncontrollable growth of CAP crystal makes it difficult to use
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