RO5166017 free base | CAS#1048346-74-2 | TAAR1 Receptor Agonist

MedKoo Cat#: 522565 | Name: RO5166017 free base

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Description:

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

RO-5166017 is a potent and selective agonist for the trace amine-associated receptor 1, with no significant activity at other targets. This is important for the study of the TAAR1 receptor, as while numerous other compounds are known which act as TAAR1 agonists, such as methamphetamine, MDMA and 3-iodothyronamine, all previously known TAAR1 agonists are either weak and rapidly metabolized (endogenous ligands), or have strong pharmacological activity at other targets (amphetamines, thyronamines), making it very difficult to assess which effects are due to TAAR1 activation.

Chemical Structure

RO5166017 free base

CAS#1048346-74-2 (free base)

Theoretical Analysis

MedKoo Cat#: 522565

Name: RO5166017 free base

CAS#: 1048346-74-2 (free base)

Chemical Formula: C12H17N3O

Exact Mass: 219.1372

Molecular Weight: 219.29

Elemental Analysis: C, 65.73; H, 7.81; N, 19.16; O, 7.30

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 550.00	2 Weeks
10mg	USD 950.00	2 Weeks

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Related CAS #

1048346-74-2 (free base)

Synonym

RO5166017; RO-5166017; RO 5166017;

IUPAC/Chemical Name

(S)-4-((ethyl(phenyl)amino)methyl)-4,5-dihydrooxazol-2-amine

InChi Key

PPONHQQJLWPUPH-JTQLQIEISA-N

InChi Code

InChI=1S/C12H17N3O/c1-2-15(11-6-4-3-5-7-11)8-10-9-16-12(13)14-10/h3-7,10H,2,8-9H2,1H3,(H2,13,14)/t10-/m0/s1

SMILES Code

NC1=N[C@@H](CN(CC)C2=CC=CC=C2)CO1

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, not in water

Shelf Life

>2 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

Instruction

View handling instruction

Biological target:

RO5166017 binds to TAAR1 (Kis = 31, 24, 1.9, and 2.7 nM in HEK293 cells expressing the recombinant human, cynomolgus monkey, mouse, or rat receptor, respectively). RO5166017 induces cAMP production in HEK293 cells expressing the recombinant human, cynomolgus monkey, mouse, or rat TAAR1 (EC50s = 55, 97, 3.3, and 14 nM, respectively). RO5166017 reduces the frequency of neuronal firing in mouse ventral tegmental area and dorsal raphe nucleus slices (IC50s = 1.73 and 2.99 nM, respectively). RO5166017 (0.3 mg/kg) inhibits stress-induced hyperthermia and reduces cocaine-induced hyperlocomotion in mice.

In vitro activity:

To be determined

In vivo activity:

Microinjection of RO5166017 into the VTA and prelimbic cortex decreased both cue- and drug priming-induced cocaine-seeking. Microinjection of RO5166017 into the NAc core and shell inhibited cue- and drug-induced cocaine-seeking, respectively. Reference: J Neurosci. 2017 Jan 25;37(4):882-892. https://pubmed.ncbi.nlm.nih.gov/28123023/

Preparing Stock Solutions

The following data is based on the product molecular weight 219.29 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. Liu JF, Siemian JN, Seaman R Jr, Zhang Y, Li JX. Role of TAAR1 within the Subregions of the Mesocorticolimbic Dopaminergic System in Cocaine-Seeking Behavior. J Neurosci. 2017 Jan 25;37(4):882-892. doi: 10.1523/JNEUROSCI.2006-16.2016. PMID: 28123023; PMCID: PMC5296782. 2. Siemian JN, Zhang Y, Li JX. Trace amine-associated receptor 1 agonists RO5263397 and RO5166017 attenuate quinpirole-induced yawning but not hypothermia in rats. Behav Pharmacol. 2017 Oct;28(7):590-593. doi: 10.1097/FBP.0000000000000330. PMID: 28704278; PMCID: PMC5599340.

In vitro protocol:

To be determined

In vivo protocol:

1: Alvarsson A, Zhang X, Stan TL, Schintu N, Kadkhodaei B, Millan MJ, Perlmann T, Svenningsson P. Modulation by Trace Amine-Associated Receptor 1 of Experimental Parkinsonism, l-DOPA Responsivity, and Glutamatergic Neurotransmission. J Neurosci. 2015 Oct 14;35(41):14057-69. doi: 10.1523/JNEUROSCI.1312-15.2015. PubMed PMID: 26468205. 2: Sukhanov I, Espinoza S, Yakovlev DS, Hoener MC, Sotnikova TD, Gainetdinov RR. TAAR1-dependent effects of apomorphine in mice. Int J Neuropsychopharmacol. 2014 Oct;17(10):1683-93. doi: 10.1017/S1461145714000509. Epub 2014 Jun 13. PubMed PMID: 24925023. 3: Cichero E, Espinoza S, Franchini S, Guariento S, Brasili L, Gainetdinov RR, Fossa P. Further insights into the pharmacology of the human trace amine-associated receptors: discovery of novel ligands for TAAR1 by a virtual screening approach. Chem Biol Drug Des. 2014 Dec;84(6):712-20. doi: 10.1111/cbdd.12367. Epub 2014 Jun 30. PubMed PMID: 24894156. 4: Leo D, Mus L, Espinoza S, Hoener MC, Sotnikova TD, Gainetdinov RR. Taar1-mediated modulation of presynaptic dopaminergic neurotransmission: role of D2 dopamine autoreceptors. Neuropharmacology. 2014 Jun;81:283-91. doi: 10.1016/j.neuropharm.2014.02.007. Epub 2014 Feb 22. PubMed PMID: 24565640. 5: Cichero E, Espinoza S, Gainetdinov RR, Brasili L, Fossa P. Insights into the structure and pharmacology of the human trace amine-associated receptor 1 (hTAAR1): homology modelling and docking studies. Chem Biol Drug Des. 2013 Apr;81(4):509-16. doi: 10.1111/cbdd.12018. PubMed PMID: 22883051. 6: Revel FG, Moreau JL, Pouzet B, Mory R, Bradaia A, Buchy D, Metzler V, Chaboz S, Groebke Zbinden K, Galley G, Norcross RD, Tuerck D, Bruns A, Morairty SR, Kilduff TS, Wallace TL, Risterucci C, Wettstein JG, Hoener MC. A new perspective for schizophrenia: TAAR1 agonists reveal antipsychotic- and antidepressant-like activity, improve cognition and control body weight. Mol Psychiatry. 2013 May;18(5):543-56. doi: 10.1038/mp.2012.57. Epub 2012 May 29. PubMed PMID: 22641180. 7: Revel FG, Moreau JL, Gainetdinov RR, Bradaia A, Sotnikova TD, Mory R, Durkin S, Zbinden KG, Norcross R, Meyer CA, Metzler V, Chaboz S, Ozmen L, Trube G, Pouzet B, Bettler B, Caron MG, Wettstein JG, Hoener MC. TAAR1 activation modulates monoaminergic neurotransmission, preventing hyperdopaminergic and hypoglutamatergic activity. Proc Natl Acad Sci U S A. 2011 May 17;108(20):8485-90. doi: 10.1073/pnas.1103029108. Epub 2011 Apr 27. PubMed PMID: 21525407; PubMed Central PMCID: PMC3101002.

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AUM 00793