Ephenidine

Summary

Ephenidine, also recognized under the aliases NEDPA and EPE, is categorized as a dissociative anaesthetic with a history of availability as a designer drug via online markets. While its legality status varies globally, certain nations have prohibited it due to its structural resemblance to the banned opioid, lefetamine. Nevertheless, Ephenidine continues to be commercially available in regions where it remains legal.

Identifiers

IUPAC name
CAS Number	60951-19-1HCl: 6272-97-5
PubChem CID	110821HCl: 110820
ChemSpider	99470HCl: 99469
UNII	NG69VG2948
Chemical and physical data
Formula	C16H19N
Molar mass	225.335 g·mol−1

Pharmacology

Pharmacodynamics:
Ephedrine and its related diarylethylamines have been subject to in vitro research aimed at evaluating their potential as treatments for neurotoxic injuries. They exhibit antagonistic properties towards the NMDA receptor, with ephedrine displaying a binding affinity (Ki = 66.4 nM). Furthermore, ephedrine demonstrates lesser affinities for dopamine and norepinephrine transporters, measuring 379 nM and 841 nM, respectively. It also interacts with σ1R (629 nM) and σ2R (722 nM) binding sites.[10]
Metabolism:
The metabolic transformation of phenetidine follows a specific pathway. This process includes N-oxidation, N-dealkylation, mono- and bis-hydroxylation of the benzene ring, and hydroxylation of the phenyl ring, occurring only after N-dealkylation. Dihydroxy metabolites are further modified through methylation of one hydroxy group, while hydroxy metabolites undergo conjugation via glucuronidation or sulfation.

Chemistry

Reagent	Reaction color
Marquis	Orange > Brown
Mandelin	Green
Liebermann	Deep red > Brown (fast)
Froehde	Light Yellow

Society and culture

On June 1, 2015, a recommendation was made to classify ephenidine as a controlled substance, leading to its official scheduling in Sweden on August 18, 2015. In Canada, both MT-45 and its analogues were designated as Schedule I controlled substances. Unauthorized possession of these substances can result in a maximum prison sentence of 7 years. Additionally, in May 2016, Health Canada made amendments to the Food and Drug Regulations to categorize AH-7921 as a restricted drug. This means that only individuals associated with law enforcement agencies, those holding an exemption permit, or institutions with authorization from the Minister are permitted to possess this particular drug.

FAQ

• What is Ephenidine?
• Ephenidine is a dissociative anaesthetic and research chemical that has been marketed as a designer drug. Various aliases, including NEDPA and EPE, know it.
• Is Ephenidine Legal?
• The legality of Ephenidine varies from country to country. In some nations, it is illegal due to its structural similarity to banned substances, while in others, it remains unregulated. Always check your local laws and regulations before considering its use.
• How is Ephenidine Typically Used?
• Ephenidine is primarily used for research purposes in laboratory settings. It is not intended for human or animal consumption, and its effects on the human body are not well understood.
• What are the Pharmacological Effects of Ephenidine?
• Ephedrine is known to act as an antagonist of the NMDA receptor. It also displays some affinity for other receptors, such as dopamine and norepinephrine transporters, as well as σ1R and σ2R binding sites. However, its exact effects on these receptors are still being studied.
• Are There Any Known Side Effects or Risks?
• Due to the limited research on Ephenidine, its potential side effects and risks need to be well-documented. Its use may carry health and safety risks, and it is strongly advised to exercise caution and avoid its consumption.
• Can I Use Ephenidine for Recreational Purposes?
• Using Ephenidine for recreational purposes is strongly discouraged. It is not a regulated pharmaceutical or recreational substance, and the risks associated with its use are not well understood.
• Where Can I Buy Ephenidine?
• The availability of Ephenidine varies by region and is subject to legal restrictions. It is important to note that the online sale of designer drugs may be illegal in many places.
• Is Ephenidine Addictive?
• The addictive potential of Ephenidine is not well-known due to limited research. However, like many dissociative substances, it may carry the risk of psychological dependence.
• Is Ephenidine Safe for Human Consumption?
• Ephenidine is not intended for human consumption, and its safety for such use has not been established. Using unregulated research chemicals for human consumption can be extremely dangerous.
• Where Can I Find More Information About Ephenidine?
• If you require additional information about Ephenidine or its research applications, consult with academic and scientific sources or contact appropriate regulatory agencies to understand the legal status in your area. Always prioritize safety and compliance with local laws and regulations.

References

1. Morris H, Wallach J (July–August 2014). “Comprehensive Review of the Non-Medical Use of Dissociative Drugs from PCP to MXE”. Published in Drug Testing and Analysis, Volume 6 (7–8), pages 614–632. [doi:10.1002/dta.1620] [PMID 24678061]
2. Meyer MR, Orschiedt T, Maurer HH (February 2013). “Michaelis-Menten Kinetic Analysis of Drugs of Abuse to Estimate Their Affinity to Human P-Glycoprotein”. Published in Toxicology Letters, Volume 217 (2), pages 137–142. [doi:10.1016/j.toxlet.2012.12.012] [PMID 23273999]
3. Wink CS, Meyer GM, Wissenbach DK, Jacobsen-Bauer A, Meyer MR, Maurer HH (October 2014). “Metabolism and Detectability of Lefetamine-Derived Designer Drugs N-ethyl-1,2-diphenylethylamine (NEDPA) and N-iso-propyl-1,2-diphenylethylamine (NPDPA) in Rat Urine Using GC-MS, LC-MSn, and LC-HR-MS/MS”. Published in Drug Testing and Analysis, Volume 6 (10), pages 1038–1048. [doi:10.1002/dta.1621] [PMID 24591097]
4. Wink CS, Meyer GM, Meyer MR, Maurer HH (November 2015). “Toxicokinetics of Lefetamine and Derived Diphenylethylamine Designer Drugs – Contribution of Human Cytochrome P450 Isozymes to Their Main Phase I Metabolic Steps”. Published in Toxicology Letters, Volume 238 (3), pages 39–44. [doi:10.1016/j.toxlet.2015.08.012] [PMID 26276083]
5. Gray NM, Cheng BK (6 April 1994). “Patent EP 0346791 – 1,2-Diarylethylamines for Treatment of Neurotoxic Injury”. Published by G.D. Searle, LLC. [Archived via SureChEMBL, Retrieved 11 August 2016]
6. Berger ML, Schweifer A, Rebernik P, Hammerschmidt F (May 2009). “NMDA Receptor Affinities of 1,2-Diphenylethylamine and 1-(1,2-Diphenylethyl)Piperidine Enantiomers and Related Compounds”. Published in Bioorganic & Medicinal Chemistry, Volume 17 (9), pages 3456–3462. [doi:10.1016/j.bmc.2009.03.025] [PMID 19345586]
7. Wallach J, Kavanagh PV, McLaughlin G, Morris N, Power JD, Elliott SP, et al. (May 2015). “Preparation and Characterization of the ‘Research Chemical’ Diphenidine, Its Pyrrolidine Analogue, and Their 2,2-Diphenylethyl Isomers”. Published in Drug Testing and Analysis, Volume 7 (5), pages 358–367. [doi:10.1002/dta.1689] [PMID 25044512] [Archived PDF, Retrieved 2021-05-31]
8. Thurkauf A, Monn J, Mattson MV, Jacobson AE, Rice KC (1989). “Structural and Conformational Aspects of the Binding of Aryl-Alkyl Amines to the Phencyclidine Binding Site”. Published in NIDA Research Monograph, Volume 95, pages 51–56. [PMID 2561843] [Archived PDF, Retrieved 2016-08-11]
9. Goodson LH, Wiegand CJ, Splitter JS (November 1946). “Analgesics; n-Alkylated-1,2-Diphenylethylamines Prepared by the Leuckart Reaction”. Published in the Journal of the American Chemical Society, Volume 68 (11), pages 2174–2175. [doi:10.1021/ja01215a018] [PMID 21002222]
10. Kang H, Park P, Bortolotto ZA, Brandt SD, Colestock T, Wallach J, et al. (January 2017). “Ephenidine: A New Psychoactive Agent with Ketamine-Like NMDA Receptor Antagonist Properties”. Published in Neuropharmacology, Volume 112 (Pt A), pages 144–149. [doi:10.1016/j.neuropharm.2016.08.004] [PMC 5084681] [PMID 27520396]
11. Wink CS, Meyer GM, Zapp J, Maurer HH (February 2015). “Lefetamine, a Controlled Drug and Pharmaceutical Lead of New Designer Drugs: Synthesis, Metabolism, and Detectability in Urine and Human Liver Preparations Using GC-MS, LC-MS(n), and LC-High Resolution-MS/MS”. Published in Analytical and Bioanalytical Chemistry, Volume 407 (6), pages 1545–1557. [doi:10.1007/s00216-014-8414-3] [PMID 25577353] [S2CID 26014465]
12. “Ephenidine Reaction Results with Various Reagent Tests”. Reagent Tests UK. Published on 17 January 2016. [Archived from the original on 20 September 2018, Retrieved 23 January 2016]
13. “23 nya ämnen kan klassas som narkotika eller hälsofarlig vara” (in Swedish). Published by Folkhälsomyndigheten on 1 June 2015. [Archived from the original on 17 June 2019, Retrieved 15 August 2016]
14. Arsenault D (1 June 2016). “Regulations Amending the Food and Drug Regulations (Parts G and J — Lefetamine, AH-7921, MT-45 and W-18)”. Published in the Canada Gazette, Volume 150 (11). [Archived from the original on 2017-12-02, Retrieved 2016-11-17]