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MedKoo Cat#: 319610 | Name: Ramelteon
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Description:

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

Ramelteon is part of a class of sleep agents that selectively binds to the MT1 and MT2 receptors in the suprachiasmatic nucleus.

Chemical Structure

Ramelteon
Ramelteon
CAS#196597-26-9

Theoretical Analysis

MedKoo Cat#: 319610

Name: Ramelteon

CAS#: 196597-26-9

Chemical Formula: C16H21NO2

Exact Mass: 259.1572

Molecular Weight: 259.35

Elemental Analysis: C, 74.10; H, 8.16; N, 5.40; O, 12.34

Price and Availability

Size Price Availability Quantity
5mg USD 390.00 2 Weeks
10mg USD 580.00 2 Weeks
25mg USD 850.00 2 Weeks
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Related CAS #
No Data
Synonym
TAK-375; TAK 375; TAK375; Ramelteon. Brand name: Rozerem.
IUPAC/Chemical Name
(S)-N-(2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl)propionamide
InChi Key
YLXDSYKOBKBWJQ-LBPRGKRZSA-N
InChi Code
InChI=1S/C16H21NO2/c1-2-15(18)17-9-7-12-4-3-11-5-6-14-13(16(11)12)8-10-19-14/h5-6,12H,2-4,7-10H2,1H3,(H,17,18)/t12-/m0/s1
SMILES Code
CCC(=O)NCC[C@@H]1CCC2=C1C3=C(C=C2)OCC3
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Ramelteon is a melatonin (MT) receptor agonist and is selective for MT1 and MT2 over MT3 receptors as well as a panel of benzodiazepine, dopamine, and opiate receptors, ion channels, transporters, and enzymes. Ramelteon stimulates cAMP production in CHO cells expressing human MT1 and MT2 receptors (IC50s = 21.2 and 53.4 pM, respectively).
In vitro activity:
The findings of this study suggest that ramelteon alleviated lipopolysaccharide-induced human pulmonary microvascular endothelial cell damage by activating the Nrf2/HO-1 signaling pathway, making it an effective treatment for acute lung injury. Reference: Bioengineered. 2022 Jan;13(1):1518-1529. https://pubmed.ncbi.nlm.nih.gov/34986734/
In vivo activity:
Object memory performance was improved when ramelteon was injected in mice before training, suggesting that ramelteon specifically enhances the acquisition of object recognition memory. Acute ramelteon treatment enhances memory in quasi-natural contexts. Reference: J Pharmacol Sci. 2023 Jun;152(2):128-135. https://pubmed.ncbi.nlm.nih.gov/37169477/
Solvent mg/mL mM
Solubility
DMSO 30.0 115.67
DMF 30.0 115.67
Ethanol 25.0 96.39
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 259.35 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. Yang W, Zhang Y, Lu D, Huang T, Yan K, Wang W, Gao J. Ramelteon protects against human pulmonary microvascular endothelial cell injury induced by lipopolysaccharide (LPS) via activating nuclear factor erythroid 2-related factor 2 (Nrf2)/heme oxygenase-1 (HO-1) pathway. Bioengineered. 2022 Jan;13(1):1518-1529. doi: 10.1080/21655979.2021.2021065. PMID: 34986734; PMCID: PMC8805948. 2. Osanai K, Kobayashi Y, Otsu M, Izawa T, Sakai K, Iwashita M. Ramelteon, a selective MT1/MT2 receptor agonist, suppresses the proliferation and invasiveness of endometrial cancer cells. Hum Cell. 2017 Jul;30(3):209-215. doi: 10.1007/s13577-017-0169-7. Epub 2017 Apr 5. PMID: 28382516. 3. Kudara M, Kato-Ishikura E, Ikegaya Y, Matsumoto N. Ramelteon administration enhances novel object recognition and spatial working memory in mice. J Pharmacol Sci. 2023 Jun;152(2):128-135. doi: 10.1016/j.jphs.2023.04.002. Epub 2023 Apr 11. PMID: 37169477. 4. Armağan İ, Aşcı H, Erzurumlu Y, Özkula S, Hasseyid N, Kumbul Doğuç D, Okuyucu G, Varel A. Ramelteon and mechanism of its restorative effect in an experimental lung disease model. Toxicol Mech Methods. 2023 Mar;33(3):239-247. doi: 10.1080/15376516.2022.2156006. Epub 2022 Dec 13. PMID: 36482745.
In vitro protocol:
1. Yang W, Zhang Y, Lu D, Huang T, Yan K, Wang W, Gao J. Ramelteon protects against human pulmonary microvascular endothelial cell injury induced by lipopolysaccharide (LPS) via activating nuclear factor erythroid 2-related factor 2 (Nrf2)/heme oxygenase-1 (HO-1) pathway. Bioengineered. 2022 Jan;13(1):1518-1529. doi: 10.1080/21655979.2021.2021065. PMID: 34986734; PMCID: PMC8805948. 2. Osanai K, Kobayashi Y, Otsu M, Izawa T, Sakai K, Iwashita M. Ramelteon, a selective MT1/MT2 receptor agonist, suppresses the proliferation and invasiveness of endometrial cancer cells. Hum Cell. 2017 Jul;30(3):209-215. doi: 10.1007/s13577-017-0169-7. Epub 2017 Apr 5. PMID: 28382516.
In vivo protocol:
1. Kudara M, Kato-Ishikura E, Ikegaya Y, Matsumoto N. Ramelteon administration enhances novel object recognition and spatial working memory in mice. J Pharmacol Sci. 2023 Jun;152(2):128-135. doi: 10.1016/j.jphs.2023.04.002. Epub 2023 Apr 11. PMID: 37169477. 2. Armağan İ, Aşcı H, Erzurumlu Y, Özkula S, Hasseyid N, Kumbul Doğuç D, Okuyucu G, Varel A. Ramelteon and mechanism of its restorative effect in an experimental lung disease model. Toxicol Mech Methods. 2023 Mar;33(3):239-247. doi: 10.1080/15376516.2022.2156006. Epub 2022 Dec 13. PMID: 36482745.
1: Ishikawa H, Furugen A, Nishimura A, Umazume T, Ishikawa S, Aoyagi R, Narumi K, Okamoto K, Takekuma Y, Sugawara M, Kobayashi M. Validated UPLC-MS/MS method for quantification of melatonin receptor agonists and dual orexin receptor antagonists in human plasma and breast milk: Application to quantify suvorexant and lemborexant in clinical samples. J Pharm Biomed Anal. 2024 Dec 15;251:116432. doi: 10.1016/j.jpba.2024.116432. Epub 2024 Aug 20. PMID: 39180895. 2: Noguchi Y, Masuda R, Aizawa H, Yoshimura T. Relationship Between Melatonin Receptor Agonists and Parkinson's Disease. J Pineal Res. 2024 Aug;76(5):e13002. doi: 10.1111/jpi.13002. PMID: 39119925. 3: Mahmood NMS, Mahmud AM, Maulood IM. The vascular influence of melatonin on endothelial response to angiotensin II in diabetic rat aorta. J Bioenerg Biomembr. 2024 Jul 31. doi: 10.1007/s10863-024-10032-z. Epub ahead of print. PMID: 39083188. 4: Ron D, Deiner S. Postoperative Delirium and Neurocognitive Disorders: Updates for Providers Caring for Cancer Patients. Curr Oncol Rep. 2024 Jul 25. doi: 10.1007/s11912-024-01584-9. Epub ahead of print. PMID: 39052230. 5: Yavuz Türel G, Aslan Koşar P. Protective efficacy of ramelteon on methotrexate-induced DNA damage. Drug Chem Toxicol. 2024 Jul 10:1-7. doi: 10.1080/01480545.2024.2375300. Epub ahead of print. PMID: 38984403. 6: Takeshima M, Sakurai H, Inada K, Aoki Y, Ie K, Kise M, Yoshida E, Matsui K, Utsumi T, Shimura A, Okajima I, Kotorii N, Yamashita H, Suzuki M, Kuriyama K, Shimizu E, Mishima K, Watanabe K, Takaesu Y. Treatment strategies for insomnia in Japanese primary care physicians' practice: A Web-based questionnaire survey. BMC Prim Care. 2024 Jun 18;25(1):219. doi: 10.1186/s12875-024-02449-7. PMID: 38890610; PMCID: PMC11184713. 7: Singh G, Nguyen C, Kuschner W. Pharmacologic Sleep Aids in the Intensive Care Unit: A Systematic Review. J Intensive Care Med. 2024 Jun 17:8850666241255345. doi: 10.1177/08850666241255345. Epub ahead of print. PMID: 38881385. 8: Terao T. Suicide attempt during ramelteon addition to flunitrazepam: A case report. PCN Rep. 2024 Jan 18;3(1):e168. doi: 10.1002/pcn5.168. PMID: 38868473; PMCID: PMC11114368. 9: Kumar R, Maurya V, Avinash A, Appayee C. Nonsilyl Bicyclic Secondary Amine Catalysts for the Asymmetric Transfer Hydrogenation of α,β-Unsaturated Aldehydes. J Org Chem. 2024 Jun 21;89(12):8586-8600. doi: 10.1021/acs.joc.4c00523. Epub 2024 Jun 5. PMID: 38836633. 10: Chen CW, Yeh WL, Charoensaensuk V, Lin C, Yang LY, Xie SY, Lane HY, Lin CH, Wang YW, Tsai CF, Lu DY. Ramelteon protects against social defeat stress- associated abnormal behaviors. Pharmacol Biochem Behav. 2024 Aug;241:173794. doi: 10.1016/j.pbb.2024.173794. Epub 2024 Jun 2. PMID: 38834160. 11: Henmi R, Nakamura T, Mashimoto M, Takase F, Ozone M. Preventive Effects of Ramelteon, Suvorexant, and Lemborexant on Delirium in Hospitalized Patients With Physical Disease: A Retrospective Cohort Study. J Clin Psychopharmacol. 2024 Jul-Aug 01;44(4):369-377. doi: 10.1097/JCP.0000000000001876. Epub 2024 Jun 3. PMID: 38820374. 12: de Lima Menezes G, Sales Bezerra K, Nobre Oliveira JI, Fontenele Araújo J, Soares Galvão D, Alves da Silva R, Vogel Saivish M, Laino Fulco U. Quantum mechanics insights into melatonin and analogs binding to melatonin MT1 and MT2 receptors. Sci Rep. 2024 May 13;14(1):10922. doi: 10.1038/s41598-024-59786-x. PMID: 38740789; PMCID: PMC11091226. 13: Shin HW, Kwak JS, Choi YJ, Kim JW, You HS, Shin HJ, Jang YK. Efficacy and safety of perioperative melatonin for postoperative delirium in patients undergoing surgery: a systematic review and meta-analysis. J Int Med Res. 2024 May;52(5):3000605241239854. doi: 10.1177/03000605241239854. PMID: 38735057; PMCID: PMC11089947. 14: Mahmood NMS, Mahmud AM, Maulood IM. The roles of angiotensin-converting enzyme 2 inhibitor, melatonin and its agonist on angiotensin II reactivity in intact and denuded rat aortic rings. J Recept Signal Transduct Res. 2024 Feb;44(1):35-40. doi: 10.1080/10799893.2024.2345907. Epub 2024 Apr 26. PMID: 38666646. 15: Takeshima M, Yoshizawa K, Ogasawara M, Kudo M, Itoh Y, Ayabe N, Mishima K. Treatment Failure and Long-Term Prescription Risk for Guideline-Recommended Hypnotics in Japan. JAMA Netw Open. 2024 Apr 1;7(4):e246865. doi: 10.1001/jamanetworkopen.2024.6865. PMID: 38630476; PMCID: PMC11024780. 16: Hirata R, Katsuki NE, Shimada H, Nakatani E, Shikino K, Saito C, Amari K, Oda Y, Tokushima M, Tago M. The Administration of Lemborexant at Admission is Not Associated with Inpatient Falls: A Multicenter Retrospective Observational Study. Int J Gen Med. 2024 Mar 25;17:1139-1144. doi: 10.2147/IJGM.S452278. PMID: 38559594; PMCID: PMC10979668. 17: Ozone M, Hirota S, Ariyoshi Y, Hayashida K, Ikegami A, Habukawa M, Ohshima H, Harada D, Hiejima H, Kotorii N, Murotani K, Taninaga T, Uchimura N. Efficacy and Safety of Transitioning to Lemborexant from Z-drug, Suvorexant, and Ramelteon in Japanese Insomnia Patients: An Open-label, Multicenter Study. Adv Ther. 2024 Apr;41(4):1728-1745. doi: 10.1007/s12325-024-02811-2. Epub 2024 Mar 9. PMID: 38460107; PMCID: PMC10960898. 18: Burke CA, Nitti VW, Stothers L. Melatonin and melatonin receptor agonists in the treatment of nocturia: A systematic review. Neurourol Urodyn. 2024 Apr;43(4):826-839. doi: 10.1002/nau.25443. Epub 2024 Mar 8. PMID: 38456646. 19: Khafaji AWM, Al-Zubaidy AAK, Farhood IG, Salman HR. Ameliorative effects of topical ramelteon on imiquimod-induced psoriasiform inflammation in mice. Naunyn Schmiedebergs Arch Pharmacol. 2024 Aug;397(8):6231-6248. doi: 10.1007/s00210-024-03017-7. Epub 2024 Mar 6. PMID: 38446218. 20: Fornaro M, Caiazza C, Rossano F, Cilmi F, De Prisco M, Vieta E, Thompson T, Solmi M, Carvalho AF, Iasevoli F, de Bartolomeis A. Residual effects of medications for sleep disorders on driving performance: A systematic review and network meta-analysis of randomized controlled trials: NMA driving and hypnotics. Eur Neuropsychopharmacol. 2024 Apr;81:53-63. doi: 10.1016/j.euroneuro.2024.01.011. Epub 2024 Feb 23. PMID: 38401406.