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Dopamine

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Name

Dopamine

EINECS 200-110-0
CAS No. 51-61-6 Density 1.248 g/cm3
PSA 66.48000 LogP 1.29930
Solubility N/A Melting Point 218-220 oC
Formula C8H11NO2 Boiling Point 337.69 °C at 760 mmHg
Molecular Weight 153.181 Flash Point 158.03 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 51-61-6 (3-Hydroxytyramine) Hazard Symbols N/A
Synonyms

Pyrocatechol,4-(2-aminoethyl)- (8CI);2-(3,4-Dihydroxyphenyl)-1-ethanamine;2-(3,4-Dihydroxyphenyl)ethylamine;3,4-Dihydroxyphenylethylamine;3-Hydroxytyramine;4-(2-Aminoethyl)-1,2-benzenediol;4-(2-Aminoethyl)catechol;Hydroxytyramin;NSC 173182;Oxytyramine;

Article Data 59

Dopamine Synthetic route

59-92-7

levodopa

51-61-6

dopamine

Conditions
ConditionsYield
With pyridoxal 5'-phosphate; aromatic L-amino acid decarboxylase In various solvent(s) at 30℃; for 48h;82%
beim Erhitzen ueber den Schmelzpunkt;
With NH4OH-NH4Cl buffer; pyridoxal 5'-phosphate at 30℃; for 0.5h; relative rate of CO2 evolution by aromatic L-amino acid decarboxylase from Micrococcus percitreus;
554-52-9

3-Methoxytyramine

51-61-6

dopamine

Conditions
ConditionsYield
With oxygen; copper(II) perchlorate; ascorbic acid In water19%
With P4502D6 Kinetics; Enzymatic reaction;
81666-88-8

3-amino-4-hydroxyphenylethylamine

51-61-6

dopamine

Conditions
ConditionsYield
With barium nitrite; sulfuric acid Diazotization.und Eingiessen der Loesung in siedende Kupfersulfat-Loesung;
120-20-7

2-(3,4-dimethoxyphenyl)-ethylamine

51-61-6

dopamine

Conditions
ConditionsYield
With hydrogenchloride at 170℃;
With hydrogen bromide at 130℃;
With hydrogenchloride at 150℃;

A

51-61-6

dopamine

B

53405-13-3, 102917-28-2

1,2,3,4-tetrahdyro-1-methylisopquinoline-7,8-diol

Conditions
ConditionsYield
In water at 180℃; for 28h; Product distribution; var. time;
57894-18-5

2-[2-(3,4-dihydroxyphenyl)ethyl]-1,3-dioxoisoindoline

51-61-6

dopamine

Conditions
ConditionsYield
With hydrazine
37034-31-4

N-(tert-butoxycarbonyl)dopamine

51-61-6

dopamine

Conditions
ConditionsYield
With methoxybenzene; trifluoroacetic acid
Multi-step reaction with 3 steps
1: caesium carbonate / acetone / 24 h / 20 °C
2: chloro-trimethyl-silane / methanol / 20 °C
3: aq. buffer / pH 7.2 / Irradiation
View Scheme
37034-22-3

N-benzyloxycarbonyl-3,4-dihydroxyphenylethylamine

51-61-6

dopamine

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal
4747-99-3

Norlaudanosolin

51-61-6

dopamine

Conditions
ConditionsYield
In water at 180℃; for 66h; Mechanism; other tetraisoquinolines;
76734-99-1

2-(3',4'-dihydroxyphenyl)-3-acetylamino-6-(N-acetyl-2''-aminoethyl)-2,3-dihydro-1,4-benzodioxin

A

51-61-6

dopamine

B

499-61-6

arterenone

C

29477-54-1

2-hydroxy-3′,4′-dihydroxyacetophenone

Conditions
ConditionsYield
With hydrogenchloride at 110℃; for 3h;

Dopamine History

The function of Dopamine (CAS NO.51-61-6) as a neurotransmitter was discovered in 1958 by Arvid Carlsson and Nils-?ke Hillarp at the Laboratory for Chemical Pharmacology of the National Heart Institute of Sweden. It was named dopamine(51-61-6) because it was a monoamine, and its synthetic precursor was 3,4-dihydroxyphenylalanine (L-DOPA). Arvid Carlsson was awarded the 2000 Nobel Prize in Physiology or Medicine for showing that dopamine(51-61-6) is not just a precursor of norepinephrine (noradrenaline) and epinephrine (adrenaline) but a neurotransmitter, as well.
Dopamine(51-61-6) was first synthesized in 1910 by George Barger and James Ewens at Wellcome Laboratories in London, England.

Dopamine Specification

The CAS registry number of Dopamine is 51-61-6. In addition, the molecular formula is C8H11NO2. It is a catecholamine neurotransmitter which present in a wide variety of animals, including both vertebrates and invertebrates. And it is produced in several areas of the brain, including the substantia nigra and the ventral tegmental area. Moreover, its main function as a hormone is to inhibit the release of prolactin from the anterior lobe of the pituitary.

Physical properties about this chemical are: (1)ACD/LogP: 0.05; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 1; (5)ACD/KOC (pH 7.4): 1; (6)#H bond acceptors: 3; (7)#H bond donors: 4; (8)#Freely Rotating Bonds: 5; (9)Polar Surface Area: 66.48 Å2; (10)Index of Refraction: 1.619; (11)Molar Refractivity: 43.101 cm3; (12)Molar Volume: 122.788 cm3; (13)Polarizability: 17.086 ×10-24cm3; (14)Surface Tension: 60.841 dyne/cm; (15)Density: 1.248 g/cm3; (16)Flash Point: 158.03 °C; (17)Enthalpy of Vaporization: 60.399 kJ/mol; (18)Boiling Point: 337.69 °C at 760 mmHg.

Preparation of Dopamine: it is synthesized by demethylation of 2-(3,4-dimethoxyphenyl)ethylamine through using hydrogen bromide.

Dopamine is synthesized by demethylation of 2-(3,4-dimethoxyphenyl)ethylamine through using hydrogen bromide

Uses of Dopamine: it can be used as a medicinal agent. And it is available as an intravenous medication acting on the sympathetic nervous system, and can increase heart rate and blood pressure. In addition, it can react with N-Methoxydiacetamide to get N-(3,4-dihydroxy-phenethyl)-acetamide. This reaction will need reagent sodium acetate and solvent dimethylformamide. The reaction time is 4.5 hours with ambient temperature. The yield is about 31%.

Dopamine can react with N-Methoxydiacetamide to get N-(3,4-dihydroxy-phenethyl)-acetamide

You can still convert the following datas into molecular structure:
(1)SMILES: c1cc(c(cc1CCN)O)O
(2)InChI: InChI=1/C8H11NO2/c9-4-3-6-1-2-7(10)8(11)5-6/h1-2,5,10-11H,3-4,9H2
(3)InChIKey: VYFYYTLLBUKUHU-UHFFFAOYAA

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LD50 unreported 1120mg/kg (1120mg/kg)   Khimiko-Farmatsevticheskii Zhurnal. Chemical Pharmaceutical Journal. For English translation, see PCJOAU. Vol. 24(4), Pg. 42, 1990.
mouse LD50 intracervical 74mg/kg (74mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Tohoku Yakka Daigaku Kenkyu Nempo. Annual Report of the Tohoku College of Pharmacy. Vol. 27, Pg. 131, 1980.
mouse LD50 intraperitoneal 950mg/kg (950mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BLOOD: HEMORRHAGE
Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 835, 1974.
mouse LD50 intravenous 59mg/kg (59mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BLOOD: HEMORRHAGE
Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 835, 1974.
rat LD50 intraperitoneal 163mg/kg (163mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
Toxicology and Applied Pharmacology. Vol. 88, Pg. 433, 1987.

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