Nicomorphine

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Nicomorphine
Nicomorphine.png
Clinical data
Synonyms3,6-Dinicotinoylmorphine
AHFS/Drugs.comInternational Drug Names
Routes of
administration
Oral, Intravenous, Rectal
ATC code
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
E number{{#property:P628}}
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Chemical and physical data
FormulaC29H25N3O5
Molar mass495.526 g/mol
3D model (JSmol)
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Nicomorphine (Vilan, Subellan, Gevilan, MorZet) is the 3,6-dinicotinate ester of morphine. It is a strong opioid agonist analgesic two to three times as potent as morphine with a side effect profile similar to that of dihydromorphine, morphine, and diamorphine. Nicomorphine was patented as Vilan by Lannacher Heilmittel Ges. m.b.H. of Austria in 1957 and was first synthesized in 1904 either there or at another firm in what was then Austria-Hungary. The hydrochloride salt is available as ampoules of 10 mg/ml solution for injection, 5 mg tablets, and 10 mg suppositories. It is possible that other manufacturers distribute 10 mg tablets and other concentrations of injectable nicomorphine in ampoules and multidose vials. It is used, particularly in the German-speaking countries and elsewhere in Central Europe and some other countries in Europe and the former USSR in particular, for post-operative, cancer, chronic non-malignant and other neuropathic pain. It is commonly used in patient-controlled analgesia (PCA) units. The usual starting dose is 5–10 mg given every 3–5 hours.

The 3,6-diesters of morphine are drugs with more rapid and complete central nervous system penetration due to increased lipid solubility and other structural considerations. The prototype for this subgroup of semi-synthetic opiates is heroin and the group also includes dipropanoylmorphine, diacetyldihydromorphine, disalicylmorphine and others. Whilst this produces an enhanced "bang" when the drug is administered intravenously, it cannot be distinguished from morphine via other routes, although the different side effect profile, including lower incidence of nausea, is very apparent.

Side effects

Nicomorphine's side effects are similar to those of other opioids and include itching, nausea and respiratory depression. It is considered by doctors to be one of the better analgesics for the comprehensive mitigation of suffering, as opposed to purely clouding the noxious pain stimulus, in the alleviation of chronic pain conditions.[1]

Legality

Nicomorphine is regulated in much the same fashion as morphine worldwide but is a Schedule I controlled substance in the United States and was never introduced there.

Nicomorphine may appear on rare occasions on the European black market and other channels for unsupervised opioid users. It can be produced as part of a mixture of salts and derivatives of morphine by end users by means of treating morphine with nicotinic anhydride or related chemicals in an analogue of the heroin homebake process.

CAS number of hydrochloride: 35055-78-8
US DEA ACSCN: 9312
Free base conversion ratios of salts:
Nicomorphine Hydrochloride: 0.93

References

  1. Vadon P, Rehak P. Comparison of the analgesic effect of nicomorphine in two different solutions (German). Wiener Medizinische Wochenschrift. 1979 Apr 30;129(8):217-20.

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