(±)-Rotigotine

Modify Date: 2024-01-02 19:40:26

(±)-Rotigotine structure	Common Name	(±)-Rotigotine
	CAS Number	92206-54-7	Molecular Weight	315.47
	Density	1.2±0.1 g/cm3	Boiling Point	470.1±45.0 °C at 760 mmHg
	Molecular Formula	C₁₉H₂₅NOS	Melting Point	N/A
	MSDS	N/A	Flash Point	238.1±28.7 °C

Use of (±)-Rotigotine

(Rac)-Rotigotine (N-0437) is a racemate of Rotigotine. Rotigotine is a full agonist of?dopamine receptor, a partial agonist of the?5-HT1A receptor, and an antagonist of the?α2B-adrenergic receptor, with?Kis of 0.71?nM, 4-15?nM, and 83?nM for the dopamine D3 receptor and D2, D5, D4 receptors, and dopamine D1 receptor.

Name	6-[propyl(2-thiophen-2-ylethyl)amino]-5,6,7,8-tetrahydronaphthalen-1-ol
Synonym	More Synonyms

Description	(Rac)-Rotigotine (N-0437) is a racemate of Rotigotine. Rotigotine is a full agonist of?dopamine receptor, a partial agonist of the?5-HT1A receptor, and an antagonist of the?α2B-adrenergic receptor, with?Kis of 0.71?nM, 4-15?nM, and 83?nM for the dopamine D3 receptor and D2, D5, D4 receptors, and dopamine D1 receptor.
Related Catalog	Research Areas >> Endocrinology Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor Signaling Pathways >> GPCR/G Protein >> Dopamine Receptor Signaling Pathways >> Neuronal Signaling >> Dopamine Receptor Research Areas >> Neurological Disease Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor
Target	Ki: Dopamine receptor; 5-HT receptor[1][2]
In Vitro	Rotigotine has a 10-fold selectivity for D3 (pKi=9.2) receptors compared with D2, D4 and D5 (pKi=8.5-8.0) and a 100-fold selectivity compared with D1 receptors (pKi=7.2). In functional studies, Rotigotine behaves as full agonist at all dopamine receptors but notably the potency for stimulation of D1 receptors is similar to that for D2 and D3 receptors (pEC50?respectively: 9.0, 9.4-8.6, 9.7)[1]. Rotigotine (10 μM) decreases the number of THir neurons by 40% in primary mesencephalic cell culture. Rotigotine (0.01 μM) slightly protects dopaminergic neurons against MPP+?toxicity, significantly protects dopaminergic neurons against rotenone-induced cell death, and significantly inhibits ROS production by rotenone[4]. .
References	[1]. Wood M, et al. Rotigotine is a potent agonist at dopamine D1 receptors as well as at dopamine D2 and D3 receptors. Br J Pharmacol. 2015 Feb;172(4):1124-35. [2]. Scheller D, et al. The in vitro receptor profile of rotigotine: a new agent for the treatment of Parkinson's disease. Naunyn Schmiedebergs Arch Pharmacol. 2009 Jan;379(1):73-86. [3]. Fenu S, et al. In vivo dopamine agonist properties of rotigotine: Role of D1 and D2 receptors. Eur J Pharmacol. 2016 Oct 5;788:183-91. [4]. Radad K, et al. Neuroprotective effect of rotigotine against complex I inhibitors, MPP+ and rotenone, in primary mesencephalic cell culture. Folia Neuropathol. 2014;52(2):179-86.

Density	1.2±0.1 g/cm3
Boiling Point	470.1±45.0 °C at 760 mmHg
Molecular Formula	C₁₉H₂₅NOS
Molecular Weight	315.47
Flash Point	238.1±28.7 °C
Exact Mass	315.165680
PSA	51.71000
LogP	4.96
Vapour Pressure	0.0±1.2 mmHg at 25°C
Index of Refraction	1.611

HS Code	2934999090

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Literature: SHAN DONG LUYE PHARMACEUTICAL CO., LTD.; Meng, Qingguo; Yang, Mina; Wang, Tao; Wang, Qilin; Li, Jun; Ruan, Zheng Patent: US2014/121380 A1, 2014 ; Location in patent: Paragraph 0059 ;

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Precursor 6
CAS#:40412-06-4 2-(2-Thienyl)et... CAS#:78950-82-0 rac-5,6,7,8-Tet... CAS#:1918-77-0 2-Thienylacetic acid CAS#:32940-15-1 5-Methoxy-2-tet...
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DownStream 0

HS Code	2934999090
Summary	2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

6-(Propyl(2-(2-thienyl)ethyl)amino)-5,6,7,8-tetrahydro-1-naphthalenol

6-{Propyl[2-(2-thienyl)ethyl]amino}-5,6,7,8-tetrahydro-1-naphthalenol

5-hydroxy-2-(N-n-propyl-N-2-ethylthienyl-amino)tetralin

1-Naphthalenol, 5,6,7,8-tetrahydro-6-[propyl[2-(2-thienyl)ethyl]amino]-

6-{propyl[2-(thiophen-2-yl)ethyl]amino}-5,6,7,8-tetrahydronaphthalen-1-ol

UNII:5QTR54Z0E1

rotigotine transdermal patch

N-0437

ent-Rotigotine

ROTIGOTINE, (±)-

1-Naphthalenol, 5,6,7,8-tetrahydro-6-(propyl(2-(2-thienyl)ethyl)amino)-

(-)-5,6,7,8-tetrahydro-6-[propyl[2-(thien-2-yl)ethyl]-amino]-1-naphthol

6-{Propyl[2-(2-thienyl)ethyl]amino}-5,6,7,8-tetrahydronaphthalen-1-ol

2-(N-propyl-N-(2-thiofuranyl)-2'-ethylamino)-5-hydroxy-1,2,3,4-tetrahydronaphthalene

[3H]-N 0437

(±)-Rotigotine

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(±)-Rotigotine Biological Activity

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