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MedKoo Cat#: 585130 | Name: Rilmenidine
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Description:

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

Rilmenidine is an antihypertensive agent.

Chemical Structure

Rilmenidine
Rilmenidine
CAS#54187-04-1

Theoretical Analysis

MedKoo Cat#: 585130

Name: Rilmenidine

CAS#: 54187-04-1

Chemical Formula: C10H16N2O

Exact Mass: 180.1263

Molecular Weight: 180.25

Elemental Analysis: C, 66.63; H, 8.95; N, 15.54; O, 8.88

Price and Availability

Size Price Availability Quantity
100mg USD 550.00 2 Weeks
500mg USD 950.00 2 Weeks
1g USD 1,650.00 2 Weeks
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Related CAS #
207572-68-7
Synonym
Rilmenidine; S 3341; S3341; S-3341; Oxaminozoline; NSC 664312; NSC664312; NSC-664312;
IUPAC/Chemical Name
Oxazolidine, 2-((dicyclopropylmethyl)imino)-
InChi Key
CQXADFVORZEARL-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H16N2O/c1-2-7(1)9(8-3-4-8)12-10-11-5-6-13-10/h7-9H,1-6H2,(H,11,12)
SMILES Code
C1(/OCCN1)=N/C(C2CC2)C3CC3
Appearance
Solid powder
Purity
>95% (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
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO, DMF, and ethanol
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:
Rilmenidine binds to imidazole receptors in bovine rostral ventrolateral medulla homogenates (Ki = 6.1 nM), as well as α2-adrenergic receptors in bovine prefrontal cortex homogenates (Ki = 87 nM). Rilmenidine induces hypotension and bradycardia in anesthetized rats (ED50s = 0.25 and 0.35 mg/kg, respectively). It also reduces mean arterial pressure and renal sympathetic nerve activity in a rabbit model of renal hypertension induced by a renal artery clip when administered at a dose of 2.5 mg/kg. Rilmenidine (1 µM) increases levels of LC3-II, a marker of autophagy, in PC12 cells.
In vitro activity:
Rilmenidine modulates proliferation and stimulates the proapoptotic protein Bax, inducing the perturbation of the mitochondrial pathway and apoptosis in human leukemic K562 cells. Rilmenidine renders K562 cells susceptible to doxorubicin. The rilmenidine co-treatment with doxorubicin reverses G2/M arrest and triggers apoptotic response to DNA damage. Reference: Eur J Pharm Sci. 2016 Jan 1;81:172-80. https://pubmed.ncbi.nlm.nih.gov/26598394/
In vivo activity:
This study shows that treating Caenorhabditis elegans with rilmenidine at young and older ages increases lifespan. Transcriptional changes similar to caloric restriction were observed in liver and kidney tissues in mice treated with rilmenidine. Rilmenidine has a geroprotective and potential caloric restriction mimetic effect. Reference: Aging Cell. 2023 Feb;22(2):e13774. https://pubmed.ncbi.nlm.nih.gov/36670049/
Solvent mg/mL mM
Solubility
DMF 30.0 166.44
DMSO 30.0 166.44
Ethanol 30.0 166.44
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 180.25 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.

Recalculate based on batch purity %
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. Srdic-Rajic T, Nikolic K, Cavic M, Djokic I, Gemovic B, Perovic V, Veljkovic N. Rilmenidine suppresses proliferation and promotes apoptosis via the mitochondrial pathway in human leukemic K562 cells. Eur J Pharm Sci. 2016 Jan 1;81:172-80. doi: 10.1016/j.ejps.2015.10.017. Epub 2015 Oct 24. PMID: 26598394. 2. Li F, Wu N, Su RB, Liu Y, Lu XQ, Li J. Comparison of agmatine with moxonidine and rilmenidine in morphine dependence in vitro: role of imidazoline I(1) receptors. Eur J Pharmacol. 2009 Jun 10;612(1-3):1-8. doi: 10.1016/j.ejphar.2009.03.077. Epub 2009 Apr 6. PMID: 19356733. 3. Bennett DF, Goyala A, Statzer C, Beckett CW, Tyshkovskiy A, Gladyshev VN, Ewald CY, de Magalhães JP. Rilmenidine extends lifespan and healthspan in Caenorhabditis elegans via a nischarin I1-imidazoline receptor. Aging Cell. 2023 Feb;22(2):e13774. doi: 10.1111/acel.13774. Epub 2023 Jan 20. PMID: 36670049; PMCID: PMC9924948. 4. Underwood BR, Green-Thompson ZW, Pugh PJ, Lazic SE, Mason SL, Griffin J, Jones PS, Rowe JB, Rubinsztein DC, Barker RA. An open-label study to assess the feasibility and tolerability of rilmenidine for the treatment of Huntington's disease. J Neurol. 2017 Dec;264(12):2457-2463. doi: 10.1007/s00415-017-8647-0. Epub 2017 Oct 26. PMID: 29075837; PMCID: PMC5688221.
In vitro protocol:
1. Srdic-Rajic T, Nikolic K, Cavic M, Djokic I, Gemovic B, Perovic V, Veljkovic N. Rilmenidine suppresses proliferation and promotes apoptosis via the mitochondrial pathway in human leukemic K562 cells. Eur J Pharm Sci. 2016 Jan 1;81:172-80. doi: 10.1016/j.ejps.2015.10.017. Epub 2015 Oct 24. PMID: 26598394. 2. Li F, Wu N, Su RB, Liu Y, Lu XQ, Li J. Comparison of agmatine with moxonidine and rilmenidine in morphine dependence in vitro: role of imidazoline I(1) receptors. Eur J Pharmacol. 2009 Jun 10;612(1-3):1-8. doi: 10.1016/j.ejphar.2009.03.077. Epub 2009 Apr 6. PMID: 19356733.
In vivo protocol:
1. Bennett DF, Goyala A, Statzer C, Beckett CW, Tyshkovskiy A, Gladyshev VN, Ewald CY, de Magalhães JP. Rilmenidine extends lifespan and healthspan in Caenorhabditis elegans via a nischarin I1-imidazoline receptor. Aging Cell. 2023 Feb;22(2):e13774. doi: 10.1111/acel.13774. Epub 2023 Jan 20. PMID: 36670049; PMCID: PMC9924948. 2. Underwood BR, Green-Thompson ZW, Pugh PJ, Lazic SE, Mason SL, Griffin J, Jones PS, Rowe JB, Rubinsztein DC, Barker RA. An open-label study to assess the feasibility and tolerability of rilmenidine for the treatment of Huntington's disease. J Neurol. 2017 Dec;264(12):2457-2463. doi: 10.1007/s00415-017-8647-0. Epub 2017 Oct 26. PMID: 29075837; PMCID: PMC5688221.
1: Perera ND, Sheean RK, Lau CL, Shin YS, Beart PM, Horne MK, Turner BJ. Rilmenidine promotes MTOR-independent autophagy in the mutant SOD1 mouse model of amyotrophic lateral sclerosis without slowing disease progression. Autophagy. 2018;14(3):534-551. doi: 10.1080/15548627.2017.1385674. Epub 2017 Dec 17. PubMed PMID: 28980850; PubMed Central PMCID: PMC5915012. 2: Rubinsztein DC, Bento CF, Deretic V. Therapeutic targeting of autophagy in neurodegenerative and infectious diseases. J Exp Med. 2015 Jun 29;212(7):979-90. doi: 10.1084/jem.20150956. Epub 2015 Jun 22. Review. PubMed PMID: 26101267; PubMed Central PMCID: PMC4493419. 3: Lim K, Jackson KL, Burke SL, Head GA. The Effects of Rilmenidine and Perindopril on Arousal Blood Pressure during 24 Hour Recordings in SHR. PLoS One. 2016 Dec 21;11(12):e0168425. doi: 10.1371/journal.pone.0168425. eCollection 2016. PubMed PMID: 28002478; PubMed Central PMCID: PMC5176293. 4: INN Common stem: -onidine. Prescrire Int. 2017 Apr;26(181):92. PubMed PMID: 30730657. 5: Mercer LD, Higgins GC, Lau CL, Lawrence AJ, Beart PM. MDMA-induced neurotoxicity of serotonin neurons involves autophagy and rilmenidine is protective against its pathobiology. Neurochem Int. 2017 May;105:80-90. doi: 10.1016/j.neuint.2017.01.010. Epub 2017 Jan 23. PubMed PMID: 28122248. 6: Kawada T, Hayama Y, Nishikawa T, Yamamoto H, Tanaka K, Sugimachi M. Even weak vasoconstriction from rilmenidine can be unmasked in vivo by opening the baroreflex feedback loop. Life Sci. 2019 Feb 15;219:144-151. doi: 10.1016/j.lfs.2019.01.009. Epub 2019 Jan 7. PubMed PMID: 30630007. 7: Underwood BR, Green-Thompson ZW, Pugh PJ, Lazic SE, Mason SL, Griffin J, Jones PS, Rowe JB, Rubinsztein DC, Barker RA. An open-label study to assess the feasibility and tolerability of rilmenidine for the treatment of Huntington's disease. J Neurol. 2017 Dec;264(12):2457-2463. doi: 10.1007/s00415-017-8647-0. Epub 2017 Oct 26. PubMed PMID: 29075837; PubMed Central PMCID: PMC5688221. 8: Montastruc JL, Macquin-Mavier I, Tran MA, Damase-Michel C, Koenig-Berard E, Valet P. Recent advances in the pharmacology of rilmenidine. Am J Med. 1989 Sep 18;87(3C):14S-17S. Review. PubMed PMID: 2571291. 9: Nascimento AR, Machado MV, Gomes F, Vieira AB, Gonçalves-de-Albuquerque CF, Lessa MA, Bousquet P, Tibiriçá E. Central Sympathetic Modulation Reverses Microvascular Alterations in a Rat Model of High-Fat Diet-Induced Metabolic Syndrome. Microcirculation. 2016 May;23(4):320-9. doi: 10.1111/micc.12280. PubMed PMID: 27086551. 10: Vucicevic J, Srdic-Rajic T, Pieroni M, Laurila JM, Perovic V, Tassini S, Azzali E, Costantino G, Glisic S, Agbaba D, Scheinin M, Nikolic K, Radi M, Veljkovic N. A combined ligand- and structure-based approach for the identification of rilmenidine-derived compounds which synergize the antitumor effects of doxorubicin. Bioorg Med Chem. 2016 Jul 15;24(14):3174-83. doi: 10.1016/j.bmc.2016.05.043. Epub 2016 May 24. PubMed PMID: 27265687. 11: Lewis SJ, Jarrott B, Doyle AE. Rapid eye movement (REM)-sleep during and after continuous infusion of the oxazoline derivate S3341: a comparison with clonidine. J Hypertens Suppl. 1984 Dec;2(3):S45-7. PubMed PMID: 6599698. 12: Srdic-Rajic T, Nikolic K, Cavic M, Djokic I, Gemovic B, Perovic V, Veljkovic N. Rilmenidine suppresses proliferation and promotes apoptosis via the mitochondrial pathway in human leukemic K562 cells. Eur J Pharm Sci. 2016 Jan 1;81:172-80. doi: 10.1016/j.ejps.2015.10.017. Epub 2015 Oct 24. PubMed PMID: 26598394. 13: Nikolic K, Veljkovic N, Gemovic B, Srdic-Rajic T, Agbaba D. Imidazoline-1 receptor ligands as apoptotic agents: pharmacophore modeling and virtual docking study. Comb Chem High Throughput Screen. 2013 May;16(4):298-319. PubMed PMID: 23360165. 14: Weerasuriya K, Shaw E, Turner P. Preliminary clinical pharmacological studies of S3341, a new hypotensive agent, and comparison with clonidine in normal males. Eur J Clin Pharmacol. 1984;27(3):281-6. PubMed PMID: 6150856. 15: Mahieux F. Rilmenidine and vigilance. Review of clinical studies. Am J Med. 1989 Sep 18;87(3C):67S-72S. Review. PubMed PMID: 2571296. 16: Groenewoud G, Potgieter L, Meyer B. Bioequivalence evaluation of rilmenidine in healthy volunteers. Arzneimittelforschung. 2009;59(5):233-7. doi: 10.1055/s-0031-1296390. PubMed PMID: 19537523. 17: Genissel P, Bromet N. Pharmacokinetics of rilmenidine. Am J Med. 1989 Sep 18;87(3C):18S-23S. PubMed PMID: 2782323. 18: Dresse A, Scuvée-Moreau J. Influence of the alpha-2 agonist oxaminozoline (S3341) on firing rate of central noradrenergic and serotonergic neurons in the rat. Comparison with clonidine. Arch Int Physiol Biochim. 1986 Jun;94(2):99-106. PubMed PMID: 2430542. 19: Lewis SJ, Jarrott B, Doyle AE. Rapid eye movement sleep and the associated cardiovascular changes during and after continuous 10-day infusion of clonidine in normotensive rats: comparison with lofexidine and S3341. J Cardiovasc Pharmacol. 1987 Jun;9(6):711-8. PubMed PMID: 2442539. 20: Montastruc JL, Macquin-Mavier I, Damase-Michel C, Dard B, Tran MA, Valet P. [Current data on the pharmacology of rilmenidine]. Arch Mal Coeur Vaiss. 1989 Dec;82 Spec No 5:25-9. Review. French. PubMed PMID: 2517006.

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CP 31398 Free Base

CP 31398 Free Base