Nicomorphine

Nicomorphine

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral, Intravenous, Rectal
ATC code	N02AA04 (WHO)
Legal status
Legal status	AU: S9 (Prohibited) CA: Schedule I DE: Anlage I (Controlled) US: Schedule I
Identifiers
Synonyms	3,6-Dinicotinoylmorphine
CAS Number	639-48-5 N
PubChem (CID)	5362460
ChemSpider	4515048 Y
UNII	Y95FRL95FW Y
KEGG	D07285 Y
ECHA InfoCard	100.010.326
Chemical and physical data
Formula	C29H25N3O5
Molar mass	495.526 g/mol
3D model (Jmol)	Interactive image
SMILES 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 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 Y Key:HNDXBGYRMHRUFN-CIVUWBIHSA-N Y
NY (what is this?)

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.

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.