Name: 3-Hydroxytyramine
SKU: 51-61-6

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Basic Information

Molecular Structure:
CAS No.:	51-61-6
Name:	3-Hydroxytyramine

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

Synthetic route

: 59-92-7
levodopa

: 51-61-6
dopamine

Conditions

Conditions	Yield
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

Conditions	Yield
With oxygen; copper(II) perchlorate; ascorbic acid In water	19%
With P4502D6 Kinetics; Enzymatic reaction;

: 81666-88-8
3-amino-4-hydroxyphenylethylamine

: 51-61-6
dopamine

Conditions

Conditions	Yield
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

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

: 525-72-4, 27740-96-1, 53622-83-6, 78579-88-1
(+/-)-salsolinol

A: 51-61-6
dopamine

B: 53405-13-3, 102917-28-2
1,2,3,4-tetrahdyro-1-methylisopquinoline-7,8-diol

Conditions

Conditions	Yield
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

Conditions	Yield
With hydrazine

: 37034-31-4
N-(tert-butoxycarbonyl)dopamine

: 51-61-6
dopamine

Conditions

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

: 37034-22-3
N-benzyloxycarbonyl-3,4-dihydroxyphenylethylamine

: 51-61-6
dopamine

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal

: 4747-99-3
Norlaudanosolin

: 51-61-6
dopamine

Conditions

Conditions	Yield
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

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

...Expand

Raw Materials

463-79-6

Downstream Products

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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.

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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