Piminodine

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Piminodine

Systematic (IUPAC) name
ethyl 1-(3-anilinopropyl)-4-phenylpiperidine-4-carboxylate
Clinical data
Pregnancy cat.	?
Legal status	Schedule II (US)
Identifiers
CAS number	13495-09-5^Y
ATC code	None
PubChem	CID 21950
ChemSpider	20628^Y
UNII	3IIX447HWS^Y
Chemical data
Formula	C₂₃H₃₀N₂O₂
Mol. mass	366.497 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C23H30N2O2/c1-2-27-22(26)23(20-10-5-3-6-11-20)14-18-25(19-15-23)17-9-16-24-21-12-7-4-8-13-21/h3-8,10-13,24H,2,9,14-19H2,1H3^Y Key:PXXKIYPSXYFATG-UHFFFAOYSA-N^Y
Y(what is this?) (verify)

Piminodine (Alvodine) is an opioid analgesic that is an analogue of pethidine (meperidine).^[1] It was used in medicine briefly during the 1960s and 70s, but has largely fallen out of clinical use. It was used particularly for obstetric analgesia and in dental procedures and, like pethidine, could be combined with hydroxyzine to intensify the effects. The duration of action is 2 to 4 hours and 7.5 to 10 mg via the subcutaneous route is the most common starting dose, being equal to 80 to 100 mg of pethidine, 40 to 60 mg of alphaprodine and 10 mg of morphine. Oral formulations were also available.

Piminodine has similar effects to other opioids, and produces analgesia, sedation and euphoria. Side effects can include itching, nausea and potentially serious respiratory depression which can be life-threatening.^[2]^[3]

References

^ Sim E, Dimoglo A, Shvets N, Ahsen V. Electronic-topological study of the structure-activity relationships in a series of piperidine morphinomimetics. Current Medicinal Chemistry. 2002 Aug;9(16):1537-45.
^ Dekornfeld TJ, Lasagna L. The analgesic potency of piminodine (alvodine). Journal of Chronic Diseases. 1960 Aug;12:252-7.
^ Woods LA, Deneau GA, Bennett DR, Domino EF, Seevers MH. A comparison of the pharmacology of two potent analgesic agents, piminodine (Win 14,098-2) and Win 13,797, with morphine and meperidine. Toxicology and Applied Pharmacology. 1961 May;3:358-79.

Opioids

Opium and
poppy straw
derivatives

Crude opiate extracts/
whole opium products

Compote/Kompot/Polish heroin • Diascordium • B & O Supprettes • Dover's powder • Kendal Black Drop • Laudanum • Mithridate • Opium • Paregoric • Poppy straw concentrate • Poppy tea • Smoking opium • Theriac

Natural opiates

Opium alkaloids see also: Components of opium	Codeine • Morphine • Oripavine • Pseudomorphine • Thebaine

Alkaloid salts mixtures	Pantopon • Papaveretum (Omnopon)

Semisynthetics
including
Bentley compounds

Morphine family	2,4-Dinitrophenylmorphine • 6-Methylenedihydrodesoxymorphine • Chlornaltrexamine • Dihydrodesoxymorphine (Desomorphine) • Dihydromorphine • Hydromorphinol • Methyldesorphine • N-Phenethylnormorphine • RAM-378

3,6-diesters of morphine	Acetylpropionylmorphine • Diacetyldihydromorphine (Dihydroheroin, Acetylmorphinol) • Dibenzoylmorphine • Dipropanoylmorphine • Heroin (Diacetylmorphine) • Nicomorphine

Codeine-dionine family	6-Monoacetylcodeine • Benzylmorphine • Codeine methylbromide • Methyldihydromorphine (Dihydroheterocodeine) • Ethylmorphine (Dionine) • Heterocodeine • Morpholinylethylmorphine (Pholcodine) • Myrophine

Morphinones and morphols	14-Cinnamoyloxycodeinone • 14-Ethoxymetopon • 14-Methoxymetopon • 14-Phenylpropoxymetopon • 7-Spiroindanyloxymorphone • Acetylmorphone • Codeinone • Codorphone • Codoxime • Thebacon (Acetyldihydrocodeinone / Dihydrocodeinone enol acetate) • Hydrocodone • Hydromorphone • Metopon • Morphinone • N-Phenethyl-14-ethoxymetopon • Oxycodone • Oxymorphol • Oxymorphone • Pentamorphone • Semorphone

Morphides	Chloromorphide

Dihydrocodeine series	14-hydroxydihydrocodeine • Acetyldihydrocodeine • Dihydrocodeine • Nicocodeine • Nicodicodeine

Nitrogen morphine derivatives	Morphine-N-Oxide

Hydrazones	Oxymorphazone

Halogenated morphine derivatives	1-Iodomorphine

Active opiate
metabolites

Morphine-6-glucuronide • 6-Monoacetylmorphine • Norcodeine • Normorphine

Morphinans

Morphinan series	Cyclorphan • Dextrallorphan • Levorphanol • Levophenacylmorphan • Levomethorphan • Norlevorphanol • Oxilorphan • Phenomorphan • Methorphan / Racemethorphan • Morphanol / Racemorphanol • Ro4-1539 • Xorphanol

Others	Butorphanol • Cyprodime • Drotebanol • Nalbuphine • Sinomenine (Cocculine)

Benzomorphans

8-Carboxamidocyclazocine • Alazocine • Bremazocine • Dezocine • Ketazocine • Metazocine • Pentazocine • Phenazocine

4-Phenylpiperidines

Pethidines (Meperidines)	4-Fluoromeperidine • Allylnorpethidine • Anileridine • Benzethidine • Carperidine • Difenoxin • Diphenoxylate • Etoxeridine (Carbetidine) • Furethidine • Hydroxypethidine (Bemidone) • Morpheridine • Oxpheneridine (Carbamethidine) • Pethidine (Meperidine) • Pethidine Intermediate A • Pethidine Intermediate B (Norpethidine) • Pethidine Intermediate C (Pethidinic Acid) • Pheneridine • Phenoperidine • Piminodine • Properidine (Ipropethidine) • Sameridine

Prodines	Allylprodine • Meprodine (α-meprodine / β-meprodine) • MPPP (Desmethylprodine) • PEPAP • Prodine (α-prodine / β-prodine) • Prosidol • Trimeperidine (Promedol)

Ketobemidones	Acetoxyketobemidone • Droxypropine • Ketobemidone • Methylketobemidone • Propylketobemidone

Others	Alvimopan • Loperamide • Picenadol

Open chain
opioids

Amidones	Dipipanone • Methadone • Normethadone • Phenadoxone (Heptazone)

Methadols	Dimepheptanol (Racemethadol) • Levacetylmethadol

Moramides	Dextromoramide • Levomoramide • Racemoramide

Thiambutenes	Diethylthiambutene • Dimethylthiambutene • Ethylmethylthiambutene • Piperidylthiambutene • Pyrrolidinylthiambutene • Thiambutene • Tipepidine

Phenalkoxams	Dextropropoxyphene (Propoxyphene) • Dimenoxadol • Dioxaphetyl Butyrate • Levopropoxyphene • Norpropoxyphene

Ampromides	Diampromide • Phenampromide • Propiram

Others	IC-26 • Isoaminile • Lefetamine • R-4066

Anilidopiperidines

3-Allylfentanyl • 3-Methylfentanyl • 3-Methylthiofentanyl • 4-Phenylfentanyl • Alfentanil • α-methylacetylfentanyl • α-methylfentanyl • α-methylthiofentanyl • β-hydroxyfentanyl • β-hydroxythiofentanyl • β-methylfentanyl • Brifentanil • Carfentanil • Fentanyl • Lofentanil • Mirfentanil • Ocfentanil • Ohmefentanyl • Parafluorofentanyl • Phenaridine • Remifentanil • Sufentanil • Thiofentanyl • Trefentanil

Oripavine
derivatives

7-PET • Acetorphine • BU-48 • Buprenorphine • Cyprenorphine • Dihydroetorphine • Etorphine • Norbuprenorphine

Phenazepanes

Ethoheptazine • Meptazinol • Metheptazine • Metethoheptazine • Proheptazine

Pirinitramides

Bezitramide • Piritramide

Benzimidazoles

Clonitazene • Etonitazene

Indoles

18-MC • 7-Hydroxymitragynine • Akuammine • Eseroline • Hodgkinsine • Mitragynine • Pericine

Diphenylmethylpiperazines

BW373U86 • DPI-221 • DPI-287 • DPI-3290 • SNC-80

Opioid peptides
see also: Opioid neuropeptides

Adrenorphin • Amidorphin • Casomorphin • DADLE • DAMGO • Dermorphin • Dynorphin • Endomorphin • Endorphins • Enkephalin • Gliadorphin • Morphiceptin • Nociceptin • Octreotide • Opiorphin • Rubiscolin • TRIMU 5

Others

AD-1211 • AH-7921 • Azaprocin • BDPC • BRL-52537 • Bromadoline • C-8813 • Ciramadol • Doxpicomine • Enadoline • Faxeladol • GR-89696 • Herkinorin • ICI-199,441 • ICI-204,448 • J-113,397 • JTC-801 • Ketamine • LPK-26 • Methopholine • MT-45 • N-Desmethylclozapine • NNC 63-0532 • Nortilidine • O-Desmethyltramadol • Phencyclidine • Prodilidine • Profadol • Ro64-6198 • Salvinorin A • SB-612,111 • SC-17599 • RWJ-394,674 • TAN-67 • Tapentadol • Tifluadom • Tilidine • Tramadol • Trimebutine • U-50,488 • U-69,593 • Viminol • W-18

Opioid antagonists
&
inverse agonists

5'-Guanidinonaltrindole • Alvimopan • Chlornaltrexamine • Cyclazocine • Cyprodime • Diprenorphine (M5050) • JDTic • Levallorphan • Methylnaltrexone • Nalfurafine • Nalmefene • Naloxazone • Naloxonazine • Naloxone • Nalorphine • Naltrexol-d4 • Naltrexone • Naltriben • Naltrindole • Norbinaltorphimine • Oxilorphan

List of opioids

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