Sameridine

Sameridine
Clinical data
ATC code	none;
Identifiers
	IUPAC name N-ethyl-1-hexyl-N-methyl-4-phenylpiperidine-4-carboxamide;
CAS Number	143257-97-0;
PubChem CID	65996;
ChemSpider	59388 ;
UNII	NQP2Y50Y6B;
ChEMBL	ChEMBL2104504;
CompTox Dashboard (EPA)	DTXSID30162367 ;
Chemical and physical data
Formula	C21H34N2O
Molar mass	330.516 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(N(CC)C)C2(c1ccccc1)CCN(CCCCCC)CC2;
	InChI InChI=1S/C21H34N2O/c1-4-6-7-11-16-23-17-14-21(15-18-23,20(24)22(3)5-2)19-12-9-8-10-13-19/h8-10,12-13H,4-7,11,14-18H2,1-3H3 ; Key:TYWUGCGYWNSRPS-UHFFFAOYSA-N ;
	(verify)

Sameridine is a 4-phenyl piperidine 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.^[1] It is currently under development for use in surgical anasthesia, mainly administered by intrathecal infusion.^[2] It produces less respiratory depression than morphine, even at a high dose, and produces no respiratory depression at a low dose.^[3]

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 United States, especially if it were found to be addictive in animals.

References

^ Modalen AO, Westman L, Arlander E, Eriksson LI, Lindahl SG (February 2003). "Hypercarbic and hypoxic ventilatory responses after intrathecal administration of bupivacaine and sameridine". Anesthesia and Analgesia. 96 (2): 570–5, table of contents. doi:10.1097/00000539-200302000-00049. PMID 12538214.
^ Mulroy MF, Greengrass R, Ganapathy S, Chan V, Heierson A (April 1999). "Sameridine is safe and effective for spinal anesthesia: a comparative dose-ranging study with lidocaine for inguinal hernia repair". Anesthesia and Analgesia. 88 (4): 815–21. doi:10.1097/00000539-199904000-00025. PMID 10195530.
^ Osterlund Modalen A, Arlander E, Eriksson LI, Lindahl SG (February 2001). "The effects on hypercarbic ventilatory response of sameridine compared to morphine and placebo". Anesthesia and Analgesia. 92 (2): 529–34. doi:10.1097/00000539-200102000-00046. PMID 11159263.

External links

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[pmid12538214-1] Modalen AO, Westman L, Arlander E, Eriksson LI, Lindahl SG (February 2003). "Hypercarbic and hypoxic ventilatory responses after intrathecal administration of bupivacaine and sameridine". Anesthesia and Analgesia. 96 (2): 570–5, table of contents. doi:10.1097/00000539-200302000-00049. PMID 12538214.

[pmid10195530-2] Mulroy MF, Greengrass R, Ganapathy S, Chan V, Heierson A (April 1999). "Sameridine is safe and effective for spinal anesthesia: a comparative dose-ranging study with lidocaine for inguinal hernia repair". Anesthesia and Analgesia. 88 (4): 815–21. doi:10.1097/00000539-199904000-00025. PMID 10195530.

[pmid11159263-3] Osterlund Modalen A, Arlander E, Eriksson LI, Lindahl SG (February 2001). "The effects on hypercarbic ventilatory response of sameridine compared to morphine and placebo". Anesthesia and Analgesia. 92 (2): 529–34. doi:10.1097/00000539-200102000-00046. PMID 11159263.

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[2]

[3]

Clinical data

ATC code	none
Identifiers
IUPAC name N-ethyl-1-hexyl-N-methyl-4-phenylpiperidine-4-carboxamide
CAS Number	143257-97-0
PubChem CID	65996
ChemSpider	59388^Y
UNII	NQP2Y50Y6B
ChEMBL	ChEMBL2104504
CompTox Dashboard (EPA)	DTXSID30162367
Chemical and physical data
Formula	C₂₁H₃₄N₂O
Molar mass	330.516 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(N(CC)C)C2(c1ccccc1)CCN(CCCCCC)CC2
InChI InChI=1S/C21H34N2O/c1-4-6-7-11-16-23-17-14-21(15-18-23,20(24)22(3)5-2)19-12-9-8-10-13-19/h8-10,12-13H,4-7,11,14-18H2,1-3H3^Y Key:TYWUGCGYWNSRPS-UHFFFAOYSA-N^Y
(verify)