Sameridine

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IUPAC_name = N-ethyl-1-hexyl-N-methyl-4-phenylpiperidine-4-carboxamide

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CAS_number = 143257-97-0
synonyms = Sameridine
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PubChem = 65996
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C = 21 | H = 34 | N = 2 | O = 1
molecular_weight = 330.51 g/mol
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Sameridine is a 4-phenylpiperidine derivative that is related to the opioid analgesic drug pethidine (meperidine).

Sameridine has an unusual pharmacological profile, being both a local anaesthetic and a μ-opioid partial agonist. [Modalen AO, Westman L, Arlander E, Eriksson LI, Lindahl SG. Hypercarbic and hypoxic ventilatory responses after intrathecal administration of bupivacaine and sameridine. "Anesthesia and Analgesia". 2003 Feb;96(2):570-5.] It is currently under development for use in surgical anasthesia, mainly administered by intrathecal infusion. [Mulroy MF, Greengrass R, Ganapathy S, Chan V, Heierson A. Sameridine is safe and effective for spinal anesthesia: a comparative dose-ranging study with lidocaine for inguinal hernia repair. "Anesthesia and Analgesia". 1999 Apr;88(4):815-21.] It produces less respiratory depression than morphine, even at a high dose, and produces no respiratory depression at a low dose. [Osterlund Modalen A, Arlander E, Eriksson LI, Lindahl SG. The effects on hypercarbic ventilatory response of sameridine compared to morphine and placebo. "Anesthesia and Analgesia". 2001 Feb;92(2):529-34.]

Sameridine is not currently a controlled drug, although if approved for medical use it will certainly be a prescription medicine, and it would probably be assigned to one of the controlled drug schedules in more restrictive jurisdictions such as Australia and the USA, especially if it were found to be addictive in animals.

References

[http://www.google.com/patents?vid=USPAT5227389 Substituted 4-phenyl-4-piperidinecarboxamides with both local anaesthetic and analgesic effect. US Patent 5227389]

[http://www.google.com/patents?id=dCAeAAAAEBAJ&dq=5756748 Process for the preparation of Sameridine. US Patent 5756748]