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CAS No.: | 51-61-6 |
---|---|
Name: | 3-Hydroxytyramine |
Article Data: | 59 |
Molecular Structure: | |
Formula: | C8H11NO2 |
Molecular Weight: | 153.181 |
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; |
EINECS: | 200-110-0 |
Density: | 1.248 g/cm3 |
Melting Point: | 218-220 oC |
Boiling Point: | 337.69 °C at 760 mmHg |
Flash Point: | 158.03 °C |
PSA: | 66.48000 |
LogP: | 1.29930 |
Conditions | Yield |
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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; |
Conditions | Yield |
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With oxygen; copper(II) perchlorate; ascorbic acid In water | 19% |
With P4502D6 Kinetics; Enzymatic reaction; |
3-amino-4-hydroxyphenylethylamine
dopamine
Conditions | Yield |
---|---|
With barium nitrite; sulfuric acid Diazotization.und Eingiessen der Loesung in siedende Kupfersulfat-Loesung; |
Conditions | Yield |
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With hydrogenchloride at 170℃; | |
With hydrogen bromide at 130℃; | |
With hydrogenchloride at 150℃; |
(+/-)-salsolinol
A
dopamine
B
1,2,3,4-tetrahdyro-1-methylisopquinoline-7,8-diol
Conditions | Yield |
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In water at 180℃; for 28h; Product distribution; var. time; |
2-[2-(3,4-dihydroxyphenyl)ethyl]-1,3-dioxoisoindoline
dopamine
Conditions | Yield |
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With hydrazine |
N-(tert-butoxycarbonyl)dopamine
dopamine
Conditions | Yield |
---|---|
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 |
N-benzyloxycarbonyl-3,4-dihydroxyphenylethylamine
dopamine
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal |
Conditions | Yield |
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In water at 180℃; for 66h; Mechanism; other tetraisoquinolines; |
2-(3',4'-dihydroxyphenyl)-3-acetylamino-6-(N-acetyl-2''-aminoethyl)-2,3-dihydro-1,4-benzodioxin
A
dopamine
B
arterenone
C
2-hydroxy-3′,4′-dihydroxyacetophenone
Conditions | Yield |
---|---|
With hydrogenchloride at 110℃; for 3h; |
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.
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.
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%.
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. |