Racemoramide

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Racemoramide
Racemoramide.svg
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • 3-methyl-4-morpholin-4-yl-2,2-diphenyl-1-pyrrolidin-1-yl-butan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard 100.008.085 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C25H32N2O2
Molar mass 392.543 g·mol−1
3D model (JSmol)
  • O=C(N1CCCC1)C(c2ccccc2)(c3ccccc3)C(C)CN4CCOCC4
  • InChI=1S/C25H32N2O2/c1-21(20-26-16-18-29-19-17-26)25(22-10-4-2-5-11-22,23-12-6-3-7-13-23)24(28)27-14-8-9-15-27/h2-7,10-13,21H,8-9,14-20H2,1H3 X mark.svgN
  • Key:INUNXTSAACVKJS-UHFFFAOYSA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Racemoramide (INN, BAN), or simply moramide, is an opioid analgesic and a racemic mixture of the substances dextromoramide (the active component) and levomoramide (which is inactive), two enantiomers of a chiral molecule. [2]

Racemoramide is itself controlled; in the United States it is under Schedule I as a Narcotic with an ACSCN of 9645 and a zero annual aggregate manufacturing quota as of 2014. [3] Its salts are the bitartrate (free base conversion ratio 0.723) and dihydrochloride (0.843)

Moramide intermediate is listed separately as a Schedule II Narcotic controlled substance (ACSCN 9802), also with a zero quota. [3]

Related Research Articles

<span class="mw-page-title-main">Dextromoramide</span> Opioid analgesic drug

Dextromoramide is a powerful opioid analgesic approximately three times more potent than morphine but shorter acting. It is subject to drug prohibition regimes, both internationally through UN treaties and by the criminal law of individual states, and is usually prescribed only in the Netherlands.

<span class="mw-page-title-main">Anileridine</span> Analgesic drug

Anileridine is a synthetic analgesic drug and is a member of the piperidine class of analgesic agents developed by Merck & Co. in the 1950s. It differs from pethidine (meperidine) in that the N-methyl group of meperidine is replaced by an N-aminophenethyl group, which increases its analgesic activity.

<span class="mw-page-title-main">Methorphan</span> Group of stereoisomers

Methorphan comes in two isomeric forms, each with differing pharmacology and effects:

<span class="mw-page-title-main">Nicocodeine</span> Opioid analgesic and antitussive drug

Nicocodeine is an opioid analgesic and cough suppressant, an ester of codeine closely related to dihydrocodeine and the codeine analogue of nicomorphine. It is not commonly used in most countries, but has activity similar to other opiates. Nicocodeine and nicomorphine were introduced in 1957 by Lannacher Heilmittel of Austria. Nicocodeine is metabolised in the liver by demethylation to produce nicomorphine, also known as 6-nicotinoylmorphine, and subsequently further metabolised to morphine. Side effects are similar to those of other opiates and include itching, nausea and respiratory depression. Related opioid analogues such as nicomorphine and nicodicodeine were first synthesized. The definitive synthesis, which involves treating anhydrous codeine base with nicotinic anhydride at 130 °C, was published by Pongratz and Zirm in Monatshefte für Chemie in 1957, simultaneously with the two analogues in an article about amides and esters of various organic acids.

<span class="mw-page-title-main">Properidine</span> Chemical compound

Properidine is an opioid, an analgesic, and the isopropyl analog of pethidine. Properidine is under international control and is listed in the United States under the Controlled Substances Act (1970) as a Schedule I substance. It is a narcotic, with an Administrative Controlled Substances Code Number (ACSCN) of 9644 and a 2 gramme annual aggregate manufacturing quota as of 2014. The salt in use is hydrochloride, with a free base conversion ratio of 0.88.

<span class="mw-page-title-main">Hydroxypethidine</span> Chemical compound

Hydroxypethidine (Bemidone) is an opioid analgesic that is an analogue of the more commonly used pethidine (meperidine). Hydroxypethidine is slightly more potent than meperidine as an analgesic, 1.5x meperidine in potency, and it also has NMDA antagonist properties like its close relative ketobemidone.

<span class="mw-page-title-main">Normethadone</span> Synthetic opioid

Normethadone, also known as desmethylmethadone or phenyldimazone, is a synthetic opioid analgesic and antitussive agent. Normethadone is listed under the Single Convention on Narcotic Drugs 1961 and is a Schedule I Narcotic controlled substance in the United States, with a DEA ACSCN of 9635 and an annual manufacturing quota of 2 grams. It has a effective span of action for about 14 days, and is 12 to 20 times stronger than morphine. The salts in use are the hydrobromide, hydrochloride (0.890), methyliodide (0.675), oxalate (0.766), picrate (0.563), and the 2,6-ditertbutylnapthalindisulphonate (0.480).

<span class="mw-page-title-main">Phenampromide</span> Chemical compound

Phenampromide is an opioid analgesic from the ampromide family of drugs, related to other drugs such as propiram and diampromide. It was invented in the 1960s by American Cyanamid Co. Although never given a general release, it was trialled and 50mg codeine ≈ 60mg phenampromide. Tests on the 2 isomers showed that all of the analgesic effects were caused by the (S) isomer. In the book a 4-phenyl group added to the piperidine-ring produces a drug some x60 morphine. The potency derives from the fact that it similar in structure to fentanyl. Like fentanyl, the addition of a 4-hydroxy group to the 4-piperidylphenyl derivative increases potency to x150 morphine for the racemic compound

<span class="mw-page-title-main">Diampromide</span> Opioid analgesic drug

Diampromide is an opioid analgesic from the ampromide family of drugs, related to other drugs such as propiram and phenampromide. It was invented in the 1960s by American Cyanamid, and can be described as a ring-opened analogue of fentanyl.

<span class="mw-page-title-main">Proheptazine</span> Opioid analgesic drug

Proheptazine is an opioid analgesic related to pethidine. It was invented in the 1960s.

<span class="mw-page-title-main">Benzethidine</span> Chemical compound

Benzethidine is a 4-phenylpiperidine derivative that is related to the clinically used opioid analgesic drug pethidine.

<span class="mw-page-title-main">Pethidine intermediate A</span> Chemical compound

Pethidine intermediate A is a 4-phenylpiperidine derivative that is a precursor to the opioid analgesic drug pethidine (meperidine). It is not known to have any analgesic activity in its own right, however other derivatives of pethidine with a 4-cyano group in place of the carboxylate ethyl ester have been found to be active, so pethidine intermediate A might also show opioid effects. It is scheduled by UN Single Convention on Narcotic Drugs. It is a Schedule II Narcotic controlled substance in the United States and has an ACSCN of 9232. The 2014 annual manufacturing quota was 6 grammes.

<span class="mw-page-title-main">Hydromorphinol</span> Opioid analgesic drug

Hydromorphinol, is an opiate analogue that is a derivative of morphine, where the 14-position has been hydroxylated and the 7,8- double bond saturated. It has similar effects to morphine such as sedation, analgesia and respiratory depression, but is twice as potent as morphine and has a steeper dose-response curve and longer half-life. It is used in medicine as the bitartrate salt and hydrochloride

<span class="mw-page-title-main">Norcodeine</span> Chemical compound

Norcodeine is an opiate analogue that is the N-demethylated derivative of codeine. It has relatively little opioid activity in its own right, but is formed as a metabolite of codeine following ingestion.

<span class="mw-page-title-main">Methyldesorphine</span> Chemical compound

Methyldesorphine is an opioid analgesic. First synthesized in Germany in 1940 and patented in the US in 1952, it has a high potential for abuse as with any potent opioid agonist, and is sometimes found along with desomorphine as a component of the home-made opioid mixture known as "Krokodil" used in Russia and the neighboring former Soviet republics. It is approximately 15 times more potent than morphine as an analgesic but if the 6-7 bond is saturated, the β isomer is some 50 times more potent than morphine.

<span class="mw-page-title-main">Racemorphan</span> Racemic mixture

Racemorphan, or morphanol, is the racemic mixture of the two stereoisomers of 17-methylmorphinan-3-ol, each with differing pharmacology and effects:

<span class="mw-page-title-main">Norlevorphanol</span> Chemical compound

Norlevorphanol is an opioid analgesic of the morphinan family that was never marketed. It is the levo-isomer of 3-hydroxymorphinan (morphinan-3-ol). Norlevorphanol is a Schedule I Narcotic controlled substance in the United States with an ACSCN of 9634 and in 2014 it had an annual aggregate manufacturing quota of 52 grams. It is used as the hydrobromide and hydrochloride (0.870).

<span class="mw-page-title-main">Norpipanone</span> Opioid analgesic drug

Norpipanone is an opioid analgesic related to methadone which was developed in Germany and distributed in Hungary, Argentina, and other countries. It had originally not been under international control but upon observation of case reports of addiction it was reviewed and shortly thereafter became a controlled substance. In the United States, it is a Schedule I controlled substance. The salts in use are the hydrobromide and hydrochloride (0.902).

<span class="mw-page-title-main">Moramide intermediate</span> Chemical compound

Moramide intermediate is a moramide precursor scheduled by UN Single Convention on Narcotic Drugs.

<span class="mw-page-title-main">Methadone intermediate</span> Chemical compound

Methadone intermediate is a methadone precursor scheduled by UN Single Convention on Narcotic Drugs. It is a Schedule II Narcotic controlled substance in the United States and has an ACSCN of 9254. The 2014 annual manufacturing quota was 32 875 kilos.

References

  1. Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. Ganellin CR, Triggle DJ, Macdonald F (1997). Dictionary of pharmacological agents. CRC Press. p. 1375. ISBN   978-0-412-46630-4 . Retrieved 29 November 2011.
  3. 1 2 "Conversion Factors for Controlled Substances". Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice.