Morpheridine (Morpholinoethylnorpethidine) is a 4-

phenyl In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6 H5, and is often represented by the symbol Ph. Phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydrogen ...

piperidine Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic compound, heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless ...

derivative that is related to the clinically used

opioid Opioids are substances that act on opioid receptors to produce morphine-like effects. Medically they are primarily used for pain relief, including anesthesia. Other medical uses include suppression of diarrhea, replacement therapy for opioid us ...

analgesic An analgesic drug, also called simply an analgesic (American English), analgaesic (British English), pain reliever, or painkiller, is any member of the group of drugs used to achieve relief from pain (that is, analgesia or pain management). It ...

drug

pethidine Pethidine, also known as meperidine and sold under the brand name Demerol among others, is a synthetic opioid analgesic, pain medication of the phenylpiperidine class. Synthesized in 1938 as a potential anticholinergic agent by the German chemis ...

(meperidine). It is a strong analgesic with around 4 times the potency of pethidine, and unlike pethidine, does not cause

convulsion A convulsion is a medical condition where the body muscles contract and relax rapidly and repeatedly, resulting in uncontrolled shaking. Because epileptic seizures typically include convulsions, the term ''convulsion'' is sometimes used as a s ...

s, although it produces the standard opioid side effects such as

sedation Sedation is the reduction of irritability or agitation by administration of sedative drugs, generally to facilitate a medical procedure or diagnostic procedure. Examples of drugs which can be used for sedation include isoflurane, diethyl ether, ...

and

respiratory depression Hypoventilation (also known as respiratory depression) occurs when ventilation is inadequate (''hypo'' meaning "below") to perform needed respiratory gas exchange. By definition it causes an increased concentration of carbon dioxide (hypercapnia ...

. Morpheridine is not currently used in medicine and is a Schedule I drug which is controlled under UN drug conventions.

Synthesis

The key intermediate,

normeperidine Norpethidine (normeperidine, pethidine intermediate B) is a 4-Phenylpiperidine, 4-phenylpiperidine derivative that is both a Precursor (chemistry), precursor to, and the toxic metabolite of, pethidine (meperidine). It is scheduled by United Nati ...

, is obtained by a scheme closely akin to the parent molecule. Thus, alkylation of

benzyl cyanide Benzyl cyanide (abbreviated BnCN) is an organic compound with the chemical formula C6H5CH2CN. This colorless oily aromatic liquid is an important precursor to numerous compounds in organic chemistry. Preparation Benzyl cyanide can be produced via ...

(1) with the

tosyl In organic chemistry, a toluenesulfonyl group (tosyl group, abbreviated Ts or Tos) is a univalent functional group with the chemical formula –. It consists of a tolyl group, –, joined to a sulfonyl group, ––, with the open valence on s ...

analog of the bischloroethylamine (2) leads to the substituted piperidine (3). Basic hydrolysis serves to convert the nitrile to the acid (4). Treatment of this last with

sulfuric acid Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid ( Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen and hydrogen, with the molecular formu ...

ethanol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an Alcohol (chemistry), alcohol with the chemical formula . Its formula can be also written as or (an ethyl ...

serves both to esterify the acid and to remove the

group to yield the secondary amine (5). Alkylation of that amine by means of ''N''-(2-chloroethyl)morpholine gives morpheridine.

References

4-Phenylpiperidines Analgesics Ethyl esters 4-Morpholinyl compunds Mu-opioid receptor agonists Synthetic opioids {{analgesic-stub

Synthesis

See also

References