ChemicalBook > CAS DataBase List > 3-Hydroxytyramine

3-Hydroxytyramine

Product Name
3-Hydroxytyramine
CAS No.
51-61-6
Chemical Name
3-Hydroxytyramine
Synonyms
Dopamine;opamine;Dopamine Control;4-(2-Aminoethyl);3-Hydroxytyramine;51-61-6 3-Hydroxytyramine;3,4-Dihydroxyphenethylamine;Noradrenaline EP Impurity C;3-Hydroxytyramine USP/EP/BP;β-Hydroxytyramine (Dopamine)
CBNumber
CB72130502
Molecular Formula
C8H11NO2
Formula Weight
153.18
MOL File
51-61-6.mol
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3-Hydroxytyramine Property

Melting point:
218-220 ºC
Boiling point:
276.1°C (rough estimate)
Density 
1.1577 (rough estimate)
refractive index 
1.4770 (estimate)
storage temp. 
Hygroscopic, -20°C Freezer, Under inert atmosphere
solubility 
Aqueous Acid (Slightly), DMSO (Slightly, Heated), Methanol (Slightly)
pka
8.9(at 25℃)
form 
Solid
color 
Light Brown to Brown
Stability:
Hygroscopic
InChI
InChI=1S/C8H11NO2/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,10-11H,3-4,9H2
InChIKey
VYFYYTLLBUKUHU-UHFFFAOYSA-N
SMILES
C1(O)=CC=C(CCN)C=C1O
NIST Chemistry Reference
Dopamine(51-61-6)
EPA Substance Registry System
Dopamine (51-61-6)
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Safety

Hazardous Substances Data
51-61-6(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H361Suspected of damaging fertility or the unborn child

H400Very toxic to aquatic life

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P273Avoid release to the environment.

P281Use personal protective equipment as required.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P308+P313IF exposed or concerned: Get medical advice/attention.

P330Rinse mouth.

P391Collect spillage. Hazardous to the aquatic environment

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

TRC
Product number
A595590
Product name
Dopamine
Packaging
10mg
Price
$50
Updated
2021/12/16
Usbiological
Product number
D9000-02
Product name
Dopamine
Packaging
1mg
Price
$706
Updated
2021/12/16
Usbiological
Product number
517170
Product name
Dopamine
Packaging
96Tests
Price
$1318
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0002478
Product name
DOPAMINE
Purity
95.00%
Packaging
1G
Price
$302.4
Updated
2021/12/16
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3-Hydroxytyramine Chemical Properties,Usage,Production

Description

Dopamine, abbreviated DA, is a biosynthetic compound and neurotransmitter produced in the body from the amino acid tyrosine by several pathways. It is synthesized in the adrenal gland where it is a precursor to other hormones (see Epinephrine) and in several portions of the brain, principally the substantia nigra and hypothalamus.

Originator

Dopmin,Orion Corporation,Finland

History

Dopamine is stored in vesicles in the brain’s presynaptic nerve terminals. It is closely associated with its immediate precursor, l-Dopa (levodopa). Casmir Funk (1884–1967) first synthesized Dopa in racemic form in 1911 and considered Dopa a vitamin. In 1913, Marcus Guggenheim, a biochemist from Hoff man-LaRoche, isolated l-Dopa from seedlings of Vicia faba, the Windsor bean plant native to northern Africa and southwest Asia. Guggenheim used beans from the garden of Felix Hoff man (1868–1946), the discoverer of aspirin. Guggenheim ingested a 2.5-gram dose of l-Dopa, resulting in nausea and vomiting; he also administered small dosages to animals and did not observe any signifi cant effects. This led him to believe that l-Dopa was biologically inactive. Studies commencing in 1927 reported that Dopa played a role in glucose metabolism and aff ected arterial blood pressure. Interest in dopamine accelerated in 1938 when the German physician and pharmacologist Peter Holtz (1902–1970) and co-workers discovered the enzyme l-Dopa decarboxylase and that it converted l-Dopa into dopamine in humans and animals. Research over the next two decades focused on l-Dopa’s role as a precursor to other catecholamine hormones, its vascular effects, and its role in brain chemistry.

Uses

Adrenergic.

Uses

Dopamine exhibits its primary action of the cardiovascular system, kidneys, and mesentery. It is used as a temporary agent for treating hypotension and circulatory shock caused by myocardial stroke, trauma, kidney rejection, and endogenous septicemia. The main indication for use of this drug is shock of various origins (cardiogenic, postoperational, infectious-toxic, anaphylactic), severe hypotension, and imminent renal insufficiency.

Uses

Dopamine(3-Hydroxytyramine) is used as a drug to treat several conditions. It can be injected as a solution ofdopamine hydrochloride, such as in the drug Intropin. It is used as a stimulant to the heartmuscle to treat heart conditions; it also constricts the blood vessels, increasing systolic bloodpressure and improving blood flow through the body. Dopamine is used in renal medicationsto improve kidney function and urination. Dopamine dilates blood vessels in the kidneys,increasing the blood supply and promoting the fl ushing of wastes from the body. Dopamineis used to treat psychological disorders such as schizophrenia and paranoia.

Definition

dopamine: A catecholamine thatis a precursor in the synthesis of noradrenalineand adrenaline. It alsofunctions as a neurotransmitter inthe brain.

Manufacturing Process

To 5 g of 3,4-dimethoxyphenylethyl amine HCl was added 20 ml of concentrated HCl. The mixture was heated at 150°C for 2 hours. Then it wascooled to ambient temperature and decolored with a charcoal, filtered and deluted with ethanol. The resulting crystals was isolated and re-crystallized from acetone. The melting point of 3,4-dihydroxyphenylethylamine hydrochloride is 174°-175°C. The free base may be prepared from this product by adding of equivalent of NaOH or any other alkali.

brand name

Intropin (Mayne).

Therapeutic Function

Cardiotonic

Biological Functions

Quantitatively, dopamine is the most important of the biogenic amine neurotransmitters in the CNS.The three major distinct dopaminergic systems in the mammalian brain are categorized according to the lengths of the neurons. There is a system comprising ultrashort neurons within amacrine cells of the retina and periglomerular cells in the olfactory bulb. Of the several intermediate-length dopaminergic neuronal systems, the best studied are neurons in the tuberobasal ventral hypothalamus that innervate the median eminence and the intermediate lobe of the pituitary. These neurons are important in the regulation of various hypothalamohypophysial functions, including prolactin release from the anterior pituitary.The best-categorized of the dopamine neuronal systems are the long projections from nuclei in the substantia nigra and ventral tegmental areas to the limbic cortex; other limbic structures, including the amygdaloid complex and piriform cortex; and the neostriatum (primarily the caudate and putamen). In Parkinson’s disease, the primary biochemical feature is a marked reduction in the concentration of dopamine in this long projection system.
Several classes of drugs, notably the antipsychotics, discussed in Chapter 34, interfere with dopaminergic transmission. In general, dopamine appears to be an inhibitory neurotransmitter. Five dopamine receptors have been identified; the most important and best studied are the D1- and D2-receptor groups.The D1-receptor, which increases cyclic adenosine monophosphate (cAMP) by activation of adenylyl cyclase, is located primarily in the region of the putamen, nucleus accumbens, and in the olfactory tubercle. The D2-receptor decreases cAMP, blocks certain calcium channels, and opens certain potassium channels.

General Description

Dopamine (Intropin) acts primarily on 1-and 1-adrenergic receptors, increasing systemic vascularresistance and exerting a positive inotropic effect on theheart. It must be administered by an intravenous route, becauseoral administration results in rapid metabolism byMAO and/or catechol-O-methyltransferase (COMT).

Mechanism of action

Dopamine is found in every sympathetic neuron and ganglion in the CNS. As a drug, and in addition to stimulation of dopaminergic receptors, dopamine indirectly stimulates both α- and β-adrenoreceptors. Dopamine also causes a release of endogenous norepinephrine. The mechanism of action is based on the excitatory effect on β-adrenoreceptors (in low and moderate doses), as well as on α-adrenoreceptors (in large doses). It has a positive inotropic effect on the heart, increases blood supply, selectively widens renal and mesenteric blood vessels, does not elevate blood pressure, and slightly increases the frequency of heartbeats.

Clinical Use

Although not strictly an adrenergic drug, dopamine is a catecholamine with properties related to the cardiovascular activities of the other agents in this chapter. Dopamine acts on specific dopamine receptors to dilate renal vessels, increasing renal blood flow. Dopamine also stimulates cardiac β1-receptors through both direct and indirect mechanisms. It is used to correct hemodynamic imbalances induced by conditions such as shock, myocardial infarction, trauma, or congestive heart failure. As a catechol and primary amine, dopamine is rapidly metabolized by COMT and MAO and, similar to dobutamine, has a short duration of action with no oral activity. It is administered as an intravenous infusion.

Synthesis

As a medicinal agent, dopamine, 2-(3,4-dihydroxyphenyl)-ethylamine (11.3.1), is synthesized by demethylation of 2-(3,4-dimethoxyphenyl)ethylamine (19.4.3) using hydrogen bromide [49¨C51].

Environmental Fate

Dopamine quinones may irreversibly alter protein function through the formation of 5-cysteinyl-catechols on the proteins. The formation of dopamine quinone-alpha-synuclein consequently increases cytotoxic protofibrils and the covalent modification of tyrosine hydroxylase by dopamine quinones. The melaninsynthetic enzyme tyrosinase in the brain may rapidly oxidize excess amounts of cytosolic dopamine and prevent slowly progressive cell damage by auto-oxidation of dopamine, thus maintaining dopamine levels.

Toxicity evaluation

High concentrations of dopamine present inside of a cell than there are vesicles to store it in, oxidative stress can occur and cause damage or death to the cell. It is thought that dopamine overload causes biochemical damage to cellular mitochondria, that provide the cell with all of the energy it requires to function, resulting in death of the cell. Catecholamines produced circulatory changes that reversed propofol anesthesia in animal models.

3-Hydroxytyramine Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 3-Hydroxytyramine manufacturers

Shaanxi TNJONE Pharmaceutical Co., Ltd
Product
Dopamine 51-61-6
Price
US $0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
10000kg
Release date
2024-04-29
Hebei Yanxi Chemical Co., Ltd.
Product
dopamine 51-61-6
Price
US $0.00/kg
Min. Order
1kg
Purity
0.99
Supply Ability
20tons
Release date
2023-10-10
ShenZhen H&D Pharmaceutical Technology Co., LTD
Product
Dopamine 51-61-6
Price
US $0.00/mg
Min. Order
10mg
Purity
0.98
Supply Ability
10g
Release date
2024-04-01

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