Rilmenidine

Names

[ Name ]:
Rilmenidine

[Synonym ]:
2-Oxazolamine, N-(dicyclopropylmethyl)-4,5-dihydro-
Rilmenidine
S 3341-3
S 3341
N-(Dicyclopropylmethyl)-4,5-dihydro-2-oxazolamine
Oxaminozoline
hyperium
N-(Dicyclopropylmethyl)-4,5-dihydro-1,3-oxazol-2-amine
2-[N-(Dicyclopropylmethyl)amino]oxazoline
EINECS 259-021-0
Tenaxum
MFCD00865924

Biological Activity

[Description]:

Rilmenidine, an innovative antihypertensive agent, is an orally active, selective I1 imidazoline receptor agonist. Rilmenidine is an alpha 2-adrenoceptor agonist. Rilmenidine induces autophagy. Rilmenidine modulates proliferation and stimulates the proapoptotic protein Bax thus inducing the perturbation of the mitochondrial pathway and apoptosis in human leukemic K562 cells[1][2][3].

[Related Catalog]:

Signaling Pathways >> Neuronal Signaling >> Imidazoline Receptor

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cardiovascular Disease

Signaling Pathways >> GPCR/G Protein >> Imidazoline Receptor

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor

[In Vitro]

Rilmenidine (25-100 μM; 24 hours) inhibits K562 cell proliferation[2]. Cell Viability Assay[2] Cell Line: K562 cells Concentration: 25, 50, 100 μM Incubation Time: 24 hours Result: Dose-dependently inhibited K562 colony formation.

[In Vivo]

Rilmenidine-treated N171-82Q mice (i.p.; 4-times a week) displays significant improved forelimb grip strength and all limbs grip strength from 12 to 22 weeks of age[3].

[References]

[1]. Reid JL. Rilmenidine: a clinical overview. Am J Hypertens. 2000;13(6 Pt 2):106S-111S.

[2]. Srdic-Rajic T, et al. Rilmenidine suppresses proliferation and promotes apoptosis via the mitochondrial pathway in human leukemic K562 cells. Eur J Pharm Sci. 2016;81:172-180.

[3]. Rose C, et al. Rilmenidine attenuates toxicity of polyglutamine expansions in a mouse model of Huntington's disease. Hum Mol Genet. 2010;19(11):2144-2153.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
355.5±9.0 °C at 760 mmHg

[ Melting Point ]:
106 - 107ºC

[ Molecular Formula ]:
C₁₀H₁₆N₂O

[ Molecular Weight ]:
180.247

[ Flash Point ]:
168.8±18.7 °C

[ Exact Mass ]:
180.126266

[ PSA ]:
33.62000

[ LogP ]:
0.57

[ Vapour Pressure ]:
0.0±0.8 mmHg at 25°C

[ Index of Refraction ]:
1.711

[ Storage condition ]:
Store at -20°C

[ Water Solubility ]:
H2O: 7.3 mg/mL

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RP7207400

CHEMICAL NAME :: Oxazolidine, 2-((dicyclopropylmethyl)imino)-

CAS REGISTRY NUMBER :: 54187-04-1

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C10-H16-N2-O

MOLECULAR WEIGHT :: 180.28

WISWESSER LINE NOTATION :: T5N CO AUTJ BMY- AL3TJ&- AL3TJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 24 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Bacteria - Salmonella typhimurium

DOSE/DURATION :: 1 umol/plate

REFERENCE :: ENMUDM Environmental Mutagenesis. (New York, NY) V.1-9, 1979-87. For publisher information, see EMMUEG. Volume(issue)/page/year: 5,527,1983

Safety Information

[ Safety Phrases ]:
S22-S24/25

[ WGK Germany ]:
3

[ RTECS ]:
RP7207400

[ HS Code ]:
2934999090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2934999090

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