3-O-Methyldopamine hydrochloride

3-O-Methyldopamine hydrochloride - Names and Identifiers

Name	3-O-Methyldopamine hydrochloride
Synonyms	TIMTEC-BB SBB003882 RARECHEM AL BW 0216 TIMTEC-BB SBB000426 3-METHOXYTYRAMINE HCL 3-O-Methyldopanimehydrochloride 3-METHOXYTYRAMINE HYDROCHLORIDE 3-O-Methyldopamine hydrochloride 3-O-Methyldopamine hydrochloride, p.a. 4-(2-AMINOETHYL)-2-METHOXYPHENOL HYDROCHLORIDE
CAS	1477-68-5
EINECS	216-035-1

3-O-Methyldopamine hydrochloride - Physico-chemical Properties

Molecular Formula	C9H13NO2.ClH
Molar Mass	203.67
Melting Point	213-215 °C(lit.)
Boling Point	306.8℃ at 760 mmHg
Flash Point	9℃
Appearance	Form crystalline, color white to light brown
Storage Condition	-20°C
Stability	Stable, but may be light sensitive. Combustible. Incompatible with strong oxidizing agents.
Sensitive	Sensitive to light
MDL	MFCD00012902
Physical and Chemical Properties	Bioactive 3-Methoxypyramine (3-O-methyl Dopamine, 3MT) hydrochloride, a major extracellular metabolite of dopamine, is a neuromodulator that may be involved in motor control in some cases.
Use	An intermediate of dopamine. Calibration of instruments and devices; Evaluation methods; Working standards; Quality assurance/quality control

3-O-Methyldopamine hydrochloride - Risk and Safety

Hazard Symbols	Xi - Irritant
Risk Codes	36/37/38 - Irritating to eyes, respiratory system and skin.
Safety Description	S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S37/39 - Wear suitable gloves and eye/face protection
UN IDs	UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany	3
FLUKA BRAND F CODES	3-10
HS Code	29222990
Hazard Class	IRRITANT

3-O-Methyldopamine hydrochloride - Upstream Downstream Industry

Raw Materials	Methanol Tetrahydrofuran Dichloromethane Acetic acid N,N-Dimethylformamide Potassium carbonate Triethylamine Lithium Aluminum Hydride Palladium ZINC Benzyl chloride Ammonium acetate Vanillin Nitromethane Benzyl chloroformate 1-(4-HYDROXY-3-METHOXYPHENYL)-2-NITROETHENE 2-(4-Hydroxy-3-methoxyphenyl)acetamide Phenol, 2-methoxy-4-(2-nitroethyl)- (9CI)
Downstream Products	Dopamine

3-O-Methyldopamine hydrochloride - Nature

BRN

3631283

Last Update：2024-04-09 20:52:54

3-O-Methyldopamine hydrochloride - Uses and synthesis methods

target

Human Endogenous Metabolite

in vitro study

The intensity of the fluorescence developed is in a linear relation to the amount of 3-Methoxytyramine hydrochloride presented in the sample up to at least 1 μg. When a high concentration of dopamine is present in the reaction mixture, there is some reduction in the fluorescence derived from 3-Methoxytyramine hydrochloride.

in vivo studies

The extracellular DA metabolite 3-Methoxytyramine hydrochloride (3-MT) induces significant behavioral activation in DDD mice. This activity however, is mostly presented as a set of disorganized abnormal movements that includes tremor, head bobbing, straub tail, grooming and abnormal orofacial movements rather than normal forward activity. No effect is observed when 3-Methoxytyramine hydrochloride is infused at doses below 9 µg, at 9 µg and higher doses 3-Methoxytyramine hydrochloride dose-dependently causes transient behavioral activation with a complex set of behaviors. In particular, transient hyperactivity and stereotypy, sniffing, grooming, rearing and mild abnormal involuntary movements (AIMs) at the level of limbs is observed after infusion of 9 µg of 3-Methoxytyramine hydrochloride. Similar behaviors are also observed after 18 µg of 3-Methoxytyramine hydrochloride with the additional appearance of tremor as well as oral and whole body AIMs.

production method

It is obtained by reduction of 2-methoxy-4-(2-nitrovinyl) phenol. The mixture of 2-methoxy-4-(2-nitrovinyl) phenol, ethanol, water, zinc powder and hydrochloric acid was heated and refluxed for 3h. Cool down and let stand overnight. Filtration, the filtrate is neutralized with sodium carbonate at about 10 ℃ until pH8-8.5. Filtration, the filtrate is extracted with n-butanol. The extract was distilled under reduced pressure to recover butanol, cooled, and refluxed with hydrogen chloride-methanol for half an hour. Cooling, crystallization, filtration, filter cake washing with methanol, drying at 80 ℃ to obtain 3-O-methyldopamine hydrochloride. Yield 65-70%.

Last Update：2024-04-09 21:01:54