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MedKoo Cat#: 596218 | Name: Nalmefene free base

Description:

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

Nalmefene, also known as nalmetrene, is an opioid antagonist used primarily in the management of alcohol dependence. It has also been investigated for the treatment of other addictions such as pathological gambling. Nalmefene is an opiate derivative similar in both structure and activity to the opioid antagonist naltrexone. Advantages of nalmefene relative to naltrexone include longer half-life, greater oral bioavailability and no observed dose-dependent liver toxicity. This product is not available. This product is or maybe a controlled substance.

Chemical Structure

Nalmefene free base
Nalmefene free base
CAS#55096-26-9 (free base)

Theoretical Analysis

MedKoo Cat#: 596218

Name: Nalmefene free base

CAS#: 55096-26-9 (free base)

Chemical Formula: C21H25NO3

Exact Mass: 339.1834

Molecular Weight: 339.44

Elemental Analysis: C, 74.31; H, 7.42; N, 4.13; O, 14.14

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Related CAS #
55096-26-9 (free base) 58895-64-0 (HCl) 1228646-70-5 (HCl dihydrate) 1228646-72-7 (HCl hydrate)
Synonym
Nalmefene; Nalmefeno; ORF 11676; ORF-11676; ORF11676; JF-1; JF 1;JF1
IUPAC/Chemical Name
(4R,4aS,7aS,12bS)-3-(cyclopropylmethyl)-7-methylene-1,2,3,4,5,6,7,7a-octahydro-4aH-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,9-diol
InChi Key
WJBLNOPPDWQMCH-MBPVOVBZSA-N
InChi Code
InChI=1S/C21H25NO3/c1-12-6-7-21(24)16-10-14-4-5-15(23)18-17(14)20(21,19(12)25-18)8-9-22(16)11-13-2-3-13/h4-5,13,16,19,23-24H,1-3,6-11H2/t16-,19+,20+,21-/m1/s1
SMILES Code
OC(C1=C2[C@@]34[C@@]5([H])O1)=CC=C2C[C@@H](N(CC6CC6)CC4)[C@]3(O)CCC5=C
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
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
Certificate of Analysis
View CoA: current batch, Lot#T20R06C24
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Nalmefene is an opioid antagonist used primarily in the management of alcohol dependence.
In vitro activity:
This study investigated whether nalmefene, an opioid receptor inhibitor, could inhibit CT26 colon cancer cell growth through influencing cell glycolysis. CCK8 and transwell migration assays showed that nalmefene inhibited CT26 cells viability and migration in a concentration-dependent manner. In conclusion, the anti-tumor effect of nalmefene may be achieved by inhibiting opioid receptor and down-regulating calmodulin expression and CaMK II phosphorylation, thus inhibiting AKT-GSK-3β pathway and the glycolysis of CT26 cells. Reference: Acta Biochim Biophys Sin (Shanghai). 2018 Feb 1;50(2):156-163. https://pubmed.ncbi.nlm.nih.gov/29267844/
In vivo activity:
This study examined the effects of NMF (nalmefene) pretreatment on chronic daily extended access (4h) cocaine intravenous self-administration (IVSA) in adult male C57Bl/6J mice. Acute pretreatment of 1 mg/kg NMF significantly potentiated cocaine motivation as measured by progressive ratio breakpoint. Reference: Neuropharmacology. 2021 Jul 1;192:108590. https://pubmed.ncbi.nlm.nih.gov/33974940/

Preparing Stock Solutions

The following data is based on the product molecular weight 339.44 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. Wu Q, Chen X, Wang J, Sun P, Weng M, Chen W, Sun Z, Zhu M, Miao C. Nalmefene attenuates malignant potential in colorectal cancer cell via inhibition of opioid receptor. Acta Biochim Biophys Sin (Shanghai). 2018 Feb 1;50(2):156-163. doi: 10.1093/abbs/gmx131. PMID: 29267844. 2. Windisch KA, Morochnik M, Reed B, Kreek MJ. Nalmefene, a mu opioid receptor antagonist/kappa opioid receptor partial agonist, potentiates cocaine motivation but not intake with extended access self-administration in adult male mice. Neuropharmacology. 2021 Jul 1;192:108590. doi: 10.1016/j.neuropharm.2021.108590. Epub 2021 May 8. PMID: 33974940. 3. Browne CA, Smith T, Lucki I. Behavioral effects of the kappa opioid receptor partial agonist nalmefene in tests relevant to depression. Eur J Pharmacol. 2020 Apr 5;872:172948. doi: 10.1016/j.ejphar.2020.172948. Epub 2020 Jan 25. PMID: 31991139.
In vitro protocol:
1. Wu Q, Chen X, Wang J, Sun P, Weng M, Chen W, Sun Z, Zhu M, Miao C. Nalmefene attenuates malignant potential in colorectal cancer cell via inhibition of opioid receptor. Acta Biochim Biophys Sin (Shanghai). 2018 Feb 1;50(2):156-163. doi: 10.1093/abbs/gmx131. PMID: 29267844.
In vivo protocol:
1. Windisch KA, Morochnik M, Reed B, Kreek MJ. Nalmefene, a mu opioid receptor antagonist/kappa opioid receptor partial agonist, potentiates cocaine motivation but not intake with extended access self-administration in adult male mice. Neuropharmacology. 2021 Jul 1;192:108590. doi: 10.1016/j.neuropharm.2021.108590. Epub 2021 May 8. PMID: 33974940. 2. Browne CA, Smith T, Lucki I. Behavioral effects of the kappa opioid receptor partial agonist nalmefene in tests relevant to depression. Eur J Pharmacol. 2020 Apr 5;872:172948. doi: 10.1016/j.ejphar.2020.172948. Epub 2020 Jan 25. PMID: 31991139.
1: Guerzoni S, Pellesi L, Pini LA, Caputo F. Drug-drug interactions in the treatment for alcohol use disorders: A comprehensive review. Pharmacol Res. 2018 Apr 30;133:65-76. doi: 10.1016/j.phrs.2018.04.024. [Epub ahead of print] Review. PubMed PMID: 29719204. 2: Uhari-Väänänen J, Raasmaja A, Bäckström P, Oinio V, Carroll FI, Airavaara M, Kiianmaa K, Piepponen P. The κ-opioid receptor antagonist JDTic decreases ethanol intake in alcohol-preferring AA rats. Psychopharmacology (Berl). 2018 May;235(5):1581-1591. doi: 10.1007/s00213-018-4868-x. Epub 2018 Feb 28. PubMed PMID: 29492614. 3: Barrio P, Ortega L, Guardia J, Roncero C, Yuguero L, Gual A. Reply to Braillon et al.: Nalmefene Phase IV Study: A Seeding Flying in the Face of Evidence? Clin Drug Investig. 2018 Apr;38(4):387-388. doi: 10.1007/s40261-018-0625-5. PubMed PMID: 29480453. 4: Khouri C, Arbib F, Revol B, Pepin JL, Tamisier R. Severe central sleep apnoea associated with nalmefene: a case report. Br J Clin Pharmacol. 2018 May;84(5):1075-1076. doi: 10.1111/bcp.13547. Epub 2018 Feb 26. PubMed PMID: 29479731; PubMed Central PMCID: PMC5903229. 5: Braillon A, Taiebi F, Bernoussi A. Nalmefene Phase IV Study: A Seeding Flying in the Face of Evidence? Clin Drug Investig. 2018 Apr;38(4):385-386. doi: 10.1007/s40261-018-0628-2. PubMed PMID: 29476330. 6: Donoghue K. Commentary on Palpacuer et al. (2018): Do small effects on total alcohol consumption translate into clinical practice? Addiction. 2018 Feb;113(2):238-239. doi: 10.1111/add.14081. PubMed PMID: 29314404. 7: Urbanoski K, Cheng J, Rehm J, Kurdyak P. Frequent use of emergency departments for mental and substance use disorders. Emerg Med J. 2018 Apr;35(4):220-225. doi: 10.1136/emermed-2015-205554. Epub 2018 Jan 8. PubMed PMID: 29311114. 8: Spanagel R. Animal models of addiction. Dialogues Clin Neurosci. 2017 Sep;19(3):247-258. PubMed PMID: 29302222; PubMed Central PMCID: PMC5741108. 9: Litten RZ, Falk DE, Ryan ML, Fertig J, Leggio L. Advances in Pharmacotherapy Development: Human Clinical Studies. Handb Exp Pharmacol. 2018 Jan 3. doi: 10.1007/164_2017_79. [Epub ahead of print] PubMed PMID: 29294197. 10: Wu Q, Chen X, Wang J, Sun P, Weng M, Chen W, Sun Z, Zhu M, Miao C. Nalmefene attenuates malignant potential in colorectal cancer cell via inhibition of opioid receptor. Acta Biochim Biophys Sin (Shanghai). 2018 Feb 1;50(2):156-163. doi: 10.1093/abbs/gmx131. PubMed PMID: 29267844. 11: Salimi V, Mirzaei H, Ramezani A, Tahamtan A, Jamali A, Shahabi S, Golaram M, Minaei B, Gharagozlou MJ, Mahmoodi M, Bont L, Shokri F, Mokhtari-Azad T. Blocking of opioid receptors in experimental formaline-inactivated respiratory syncytial virus (FI-RSV) immunopathogenesis: from beneficial to harmful impacts. Med Microbiol Immunol. 2018 Apr;207(2):105-115. doi: 10.1007/s00430-017-0531-0. Epub 2017 Dec 18. PubMed PMID: 29256094. 12: Antonelli M, Ferrulli A, Sestito L, Vassallo GA, Tarli C, Mosoni C, Rando MM, Mirijello A, Gasbarrini A, Addolorato G. Alcohol addiction - the safety of available approved treatment options. Expert Opin Drug Saf. 2018 Feb;17(2):169-177. doi: 10.1080/14740338.2018.1404025. Epub 2017 Nov 20. Review. PubMed PMID: 29120249. 13: Millier A, Laramée P, Rahhali N, Aballéa S, Daeppen JB, Rehm J, Toumi M. Cost-Effectiveness of Nalmefene Added to Psychosocial Support for the Reduction of Alcohol Consumption in Alcohol-Dependent Patients With High/Very High Drinking Risk Levels: A Microsimulation Model. J Stud Alcohol Drugs. 2017 Nov;78(6):867-876. PubMed PMID: 29087821. 14: Barrio P, Ortega L, Guardia J, Roncero C, Yuguero L, Gual A. Who Receives Nalmefene and How Does It Work in the Real World? A Single-Arm, Phase IV Study of Nalmefene in Alcohol Dependent Outpatients: Baseline and 1-Month Results. Clin Drug Investig. 2018 Feb;38(2):147-155. doi: 10.1007/s40261-017-0590-4. PubMed PMID: 29080208. 15: Coppola M, Mondola R. Opioid receptor antagonists in the treatment of pathological gambling. J Opioid Manag. 2017 Jul/Aug;13(4):205-206. doi: 10.5055/jom.2017.0388. PubMed PMID: 28983886. 16: Palpacuer C, Duprez R, Huneau A, Locher C, Boussageon R, Laviolle B, Naudet F. Pharmacologically controlled drinking in the treatment of alcohol dependence or alcohol use disorders: a systematic review with direct and network meta-analyses on nalmefene, naltrexone, acamprosate, baclofen and topiramate. Addiction. 2018 Feb;113(2):220-237. doi: 10.1111/add.13974. Epub 2017 Sep 20. Review. PubMed PMID: 28940866. 17: Pujol CN, Paasche C, Laprevote V, Trojak B, Vidailhet P, Bacon E, Lalanne L. Cognitive effects of labeled addictolytic medications. Prog Neuropsychopharmacol Biol Psychiatry. 2018 Feb 2;81:306-332. doi: 10.1016/j.pnpbp.2017.09.008. Epub 2017 Sep 14. Review. PubMed PMID: 28919445. 18: Johansen KGV, Tarp S, Astrup A, Lund H, Pagsberg AK, Christensen R. Harms associated with taking nalmefene for substance use and impulse control disorders: A systematic review and meta-analysis of randomised controlled trials. PLoS One. 2017 Aug 29;12(8):e0183821. doi: 10.1371/journal.pone.0183821. eCollection 2017. Review. PubMed PMID: 28850596; PubMed Central PMCID: PMC5574613. 19: Callaghan CK, Rouine J, Dean RL, Knapp BI, Bidlack JM, Deaver DR, O'Mara SM. Antidepressant-like effects of 3-carboxamido seco-nalmefene (3CS-nalmefene), a novel opioid receptor modulator, in a rat IFN-α-induced depression model. Brain Behav Immun. 2018 Jan;67:152-162. doi: 10.1016/j.bbi.2017.08.016. Epub 2017 Aug 24. PubMed PMID: 28844812. 20: Lescut C, Gaboriau L, Carton L, Rolland B. Naltrexone- or Nalmefene-Related Buprenorphine Withdrawal: Treat It With… More Buprenorphine. J Clin Psychopharmacol. 2017 Oct;37(5):631-633. doi: 10.1097/JCP.0000000000000763. PubMed PMID: 28806388.