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1477-68-5

1477-68-5 structure
1477-68-5 structure
  • Name: 3-Methoxytyramine hydrochloride
  • Chemical Name: 3-O-Methyldopamine hydrochloride
  • CAS Number: 1477-68-5
  • Molecular Formula: C9H14ClNO2
  • Molecular Weight: 203.666
  • Catalog: Research Areas Neurological Disease
  • Create Date: 2019-02-17 11:49:12
  • Modify Date: 2024-01-06 19:45:41
  • 3-Methoxytyramine hydrochloride is an inactive metabolite of dopamine which can activate trace amine associated receptor 1 (TAAR1).
Name 3-O-Methyldopamine hydrochloride
Synonyms 3-O-Methyldopamine hydrochloride
Homovanillylamine hydrochloride
4-(2-Aminoethyl)-2-methoxyphenol hydrochloride
Phenol, 4-(2-aminoethyl)-2-methoxy-, hydrochloride (1:1)
4-(2-aminoethyl)-2-methoxyphenol,hydrochloride
MFCD00012902
EINECS 216-035-1
4-(2-Aminoethyl)-2-methoxyphenol hydrochloride (1:1)
Methoxytyramine
3-Methoxytyramine hydrochloride
Description 3-Methoxytyramine hydrochloride is an inactive metabolite of dopamine which can activate trace amine associated receptor 1 (TAAR1).
Related Catalog
Target

TAAR1[1]

In Vitro 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[1].
In Vivo 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[1].
Cell Assay The rats are killed by cervical dislocation and the brains are removed and placed on an ice-cooled glass plate. The corpora striata are dissected out and homogenized immediately or stored at -17°C until analyzed. For the estimation of 3-Methoxytyramine hydrochloride 1 mL of the neutralized perchloric acid solution is placed in a glass test tube. One millilitre of a solution of potassium ferricyanide (20 μg/mL) in concentrated ammonium hydroxide is added. After 2 min 0 to 1 mL of a solution of cysteine (1 mg/mL) is added and mixed. The fluorescence of the resulting solution is measured in a spectrophotofluorometer fitted with an interference filter in the fluorescence light path. A blank determination is made by reversing the order of the addition of the ferricyanide-ammonia solution and the solution of cysteine. Authentic 3-Methoxytyramine hydrochloride is also added to a portion of the neutralized eluate and the fluorescence developed to check for quenching[1].
Animal Admin To assess effects of 3-Methoxytyramine hydrochloride (3-MT) in normal and TAAR1-KO mice, the animals are placed in the locomotor activity chamber and 30 min later various doses of 3-Methoxytyramine hydrochloride are administered i.c.v.. To perform i.c.v. administration in this paradigm, habituated mice are removed from the experimental chamber, briefly restrained, i.c.v. injection cannula is placed into the previously implanted (one week before) guide cannula and infusion of 3-Methoxytyramine hydrochloride or vehicle is performed for 4 minutes when animal is freely moving in a home cage. After infusion, animals are put back into experimental chamber and behavior is monitored for 90 min after administration[1].
References

[1]. Sotnikova TD, et al. The dopamine metabolite 3-methoxytyramine is a neuromodulator. PLoS One. 2010 Oct 18;5(10):e13452.

[2]. Guldberg HC, et al. Some observations on the estimation of 3-methoxytyramine in brain tissue. Br J Pharmacol. 1971 Aug;42(4):505-11.
Boiling Point 306.8ºC at 760 mmHg
Melting Point 213 - 215ºC
Molecular Formula C9H14ClNO2
Molecular Weight 203.666
Flash Point 139.3ºC
Exact Mass 203.071304
PSA 55.48000
LogP 2.40430
Vapour Pressure 0.000418mmHg at 25°C
Storage condition -20°C
Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H315-H319-H335
Precautionary Statements P261-P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes F+
Risk Phrases R36/37/38
Safety Phrases 26-36
RIDADR NONH for all modes of transport
WGK Germany 3.0
HS Code 2922509090
6178-42-3 structure

6178-42-3

~78%

1477-68-5 structure

1477-68-5

Literature: Kohno; Sasao; Murahashi Bulletin of the Chemical Society of Japan, 1990 , vol. 63, # 4 p. 1252 - 1254
4468-59-1 structure

4468-59-1

~82%

1477-68-5 structure

1477-68-5

Literature: Jai, Woong Seo; Srisook, Ekaruth; Hyo, Jin Son; Hwang, Onyou; Cha, Young-Nam; Dae, Yoon Chi Bioorganic and Medicinal Chemistry Letters, 2005 , vol. 15, # 14 p. 3369 - 3373
29121-49-1 structure

29121-49-1

~%

1477-68-5 structure

1477-68-5

Literature: MILLER, James Jackson; PHILLIPS, Anthony George; LAPISH, Christopher Court; SAMMIS, Glenn Martin Patent: WO2013/20229 A1, 2013 ; Location in patent: Paragraph 0193 ; WO 2013/020229 A1
63909-38-6 structure

63909-38-6

~78%

1477-68-5 structure

1477-68-5

Literature: Kulikov, S. V.; Samartsev, M. A. Journal of Organic Chemistry USSR (English Translation), 1992 , vol. 28, # 2.2 p. 280 - 288 Zhurnal Organicheskoi Khimii, 1992 , vol. 28, # 2 p. 348 - 358
498-00-0 structure

498-00-0

~%

1477-68-5 structure

1477-68-5

Literature: Bioorganic and Medicinal Chemistry Letters, , vol. 15, # 14 p. 3369 - 3373
2426-87-1 structure

2426-87-1

~%

1477-68-5 structure

1477-68-5

Literature: Journal of Organic Chemistry USSR (English Translation), , vol. 28, # 2.2 p. 280 - 288 Zhurnal Organicheskoi Khimii, , vol. 28, # 2 p. 348 - 358
60372-07-8 structure

60372-07-8

~%

1477-68-5 structure

1477-68-5

Literature: Journal of Organic Chemistry USSR (English Translation), , vol. 28, # 2.2 p. 280 - 288 Zhurnal Organicheskoi Khimii, , vol. 28, # 2 p. 348 - 358
121-33-5 structure

121-33-5

~%

1477-68-5 structure

1477-68-5

Literature: Journal of Organic Chemistry USSR (English Translation), , vol. 28, # 2.2 p. 280 - 288 Zhurnal Organicheskoi Khimii, , vol. 28, # 2 p. 348 - 358
HS Code 2922509090
Summary 2922509090. other amino-alcohol-phenols, amino-acid-phenols and other amino-compounds with oxygen function. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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