Rotigotine | CAS#99755-59-6 (free base) | Dopamine receptor agonist

MedKoo Cat#: 471031 | Name: Rotigotine

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Rotigotine is a non-selective dopamine receptor agonist with preference for D3 receptors over D2 and D1. As such, it is an effective anti-Parkinsonian agent. Racemic rotigotine is about 50 times as potent as quinpirole, the gold standard D2 agonist.

Chemical Structure

Rotigotine

CAS#99755-59-6 (free base)

Theoretical Analysis

MedKoo Cat#: 471031

Name: Rotigotine

CAS#: 99755-59-6 (free base)

Chemical Formula: C19H25NOS

Exact Mass: 315.1657

Molecular Weight: 315.48

Elemental Analysis: C, 72.34; H, 7.99; N, 4.44; O, 5.07; S, 10.16

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 400.00
25mg	USD 700.00

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Related CAS #

99755-59-6 (free base) 125572-93-2 (HCl)

Synonym

Rotigotine, N0923, N-0923, N 0923

IUPAC/Chemical Name

(S)-6-(propyl(2-(thiophen-2-yl)ethyl)amino)-5,6,7,8-tetrahydronaphthalen-1-ol

InChi Key

KFQYTPMOWPVWEJ-INIZCTEOSA-N

InChi Code

InChI=1S/C19H25NOS/c1-2-11-20(12-10-17-6-4-13-22-17)16-8-9-18-15(14-16)5-3-7-19(18)21/h3-7,13,16,21H,2,8-12,14H2,1H3/t16-/m0/s1

SMILES Code

OC1=C2CC[C@@H](CC2=CC=C1)N(CCC)CCC3=CC=CS3

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, DMF, and ethanol

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Rotigotine is a non-selective dopamine receptor agonist with pEC50 values of 9.6, 10.4, 8.2, 7.7, and 7.7 for D1, D2, D3, D4, and D5, respectively.

In vitro activity:

Rotigotine is a high-potency agonist at human dopamine D1, D2 and D3 receptors with a lower potency at D4 and D5 receptors. Rotigotine differs from conventional dopamine D2 agonists, used in the treatment of Parkinson’s disease, such as ropinirole and pramipexole which lack activity at the D1 and D5 receptors. Reference: Br J Pharmacol. 2015 Feb;172(4):1124-35. https://pubmed.ncbi.nlm.nih.gov/25339241/

In vivo activity:

Results from this study provide a possible therapeutic application of rotigotine to prevent dopaminergic neurodegeneration in Parkinson's disease. Subcutaneous administration of rotigotine increased MT-1,2 expression in striatal astrocytes and prevented reduction of dopaminergic neurons in the substantia nigra of a 6-OHDA-lesioned mouse model of Parkinson's disease. Reference: Neurochem Int. 2020 Jan;132:104608. https://pubmed.ncbi.nlm.nih.gov/31765686/

	Solvent	mg/mL	mM
Solubility
	DMSO	20.0	63.40
	Ethanol	1.0	3.17

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 315.48 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Wood M, Dubois V, Scheller D, Gillard M. 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. doi: 10.1111/bph.12988. Epub 2015 Jan 13. PMID: 25339241; PMCID: PMC4314200. 2. Scheller D, Ullmer C, Berkels R, Gwarek M, Lübbert H. 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. doi: 10.1007/s00210-008-0341-4. Epub 2008 Aug 14. PMID: 18704368. 3. Isooka N, Miyazaki I, Kikuoka R, Wada K, Nakayama E, Shin K, Yamamoto D, Kitamura Y, Asanuma M. Dopaminergic neuroprotective effects of rotigotine via 5-HT1A receptors: Possibly involvement of metallothionein expression in astrocytes. Neurochem Int. 2020 Jan;132:104608. doi: 10.1016/j.neuint.2019.104608. Epub 2019 Nov 22. PMID: 31765686. 4. Bertaina-Anglade V, La Rochelle CD, Scheller DK. Antidepressant properties of rotigotine in experimental models of depression. Eur J Pharmacol. 2006 Oct 24;548(1-3):106-14. doi: 10.1016/j.ejphar.2006.07.022. Epub 2006 Jul 22. PMID: 16959244.

In vitro protocol:

In vivo protocol:

1. Isooka N, Miyazaki I, Kikuoka R, Wada K, Nakayama E, Shin K, Yamamoto D, Kitamura Y, Asanuma M. Dopaminergic neuroprotective effects of rotigotine via 5-HT1A receptors: Possibly involvement of metallothionein expression in astrocytes. Neurochem Int. 2020 Jan;132:104608. doi: 10.1016/j.neuint.2019.104608. Epub 2019 Nov 22. PMID: 31765686. 2. Bertaina-Anglade V, La Rochelle CD, Scheller DK. Antidepressant properties of rotigotine in experimental models of depression. Eur J Pharmacol. 2006 Oct 24;548(1-3):106-14. doi: 10.1016/j.ejphar.2006.07.022. Epub 2006 Jul 22. PMID: 16959244.

1. Wood, M., Dubois, V., Scheller, D., et al. Rotigotine is a potent agonist at dopamine D1 receptors as well as at dopamine D2 and D3 receptors. Br. J. Pharmacol. 172(4), 1124-1135 (2015).