Nicomorphine

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Nicomorphine
Structural formula
Ball-and-stick model
Clinical data
Other namesMorphine dinicotinate, 3,6-dinicotinoylmorphine
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral, Intravenous, Rectal
ATC code
Legal status
Legal status
Identifiers
JSmol)
  • O=C(O[C@H]2\C=C/[C@H]6[C@@H]5N(CC[C@@]61c4c(O[C@H]12)c(OC(=O)c3cccnc3)ccc4C5)C)c7cccnc7
  • InChI=1S/C29H25N3O5/c1-32-13-10-29-20-7-9-23(36-28(34)19-5-3-12-31-16-19)26(29)37-25-22(8-6-17(24(25)29)14-21(20)32)35-27(33)18-4-2-11-30-15-18/h2-9,11-12,15-16,20-21,23,26H,10,13-14H2,1H3/t20-,21+,23-,26-,29-/m0/s1 checkY
  • Key:HNDXBGYRMHRUFN-CIVUWBIHSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Nicomorphine (Vilan, Subellan, Gevilan, MorZet) is the 3,6-dinicotinate

diamorphine
.

Nicomorphine was first synthesized in 1904 and was patented as Vilan by Lannacher Heilmittel G.m.b.H. of Austria in 1957.

Medical Use

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.[medical citation needed] It is commonly used in patient-controlled analgesia (PCA) units. The usual starting dose is 5–10 mg given every 3–5 hours.

Side effects

Nicomorphine's

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.[2]

Chemistry

The method for synthesis of nicomorphine, which involves treating anhydrous morphine base with nicotinic anhydride at 130 °C, was published by Pongratz and Zirm in Monatshefte für Chemie in 1957,

nicodicodeine in an article about amides and esters of various organic acids.[3][4]

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

Pharmacology

Pharmacodynamics

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"[clarification needed] 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.

Pharmacokinetics

Nicomorphine is rapidly metabolized when administered by the I.V. route, having a half-life of 3 minutes, into morphine and 6-nicotinoylmorphine, the secondary active metabolite. Half lives of the metabolites were 3–15 minutes for the nicotinoyl metabolite, and 135–190 minutes for morphine.[5]

Via the

epidural route, a much slower release from epidural space occurs and nicomorphine remains detectable for 1.5 hours or so, and has a longer effect of 18.2 +/- 10.1 hours due to slower release of the active metabolites, morphine and 6-nicotinoylmorphine. Half lives for those compounds is listed in the IV route.[6]

Pharmacokinetics via the rectal route differ, and change metabolism. Eight minutes after administration, morphine appeared rapidly, and had a half life of 1.48 +/- 0.48h. This was in turn metabolized to morphine-3- and morphine-6-glucoranides after another 12 minutes, which had similar half-lives to one-another, at about 2.8h. No 6-mononicotinoylmorphine was found, and bioavailability of morphine and metabolic actives was 88%. No remaining nicomorphine was found in urine.[7]

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. PMID 452619
    .
  3. ^
    ISBN 978-3-642-47985-4
    .
  4. PMID 13847637
    .
  5. PMID 8462537
    .
  6. S2CID 27052829
    .
  7. S2CID 2115715
    .
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