Benzylmorphine (Peronine) is a

semi-synthetic Semisynthesis, or partial chemical synthesis, is a type of chemical synthesis that uses chemical compounds isolated from natural sources (such as microbial cell cultures or plant material) as the starting materials to produce novel compounds with ...

opioid narcotic introduced to the international market in 1896 and that of the United States very shortly thereafter. It is much like codeine, containing a benzyl group attached to the

morphine Morphine is a strong opiate that is found naturally in opium, a dark brown resin in poppies (''Papaver somniferum''). It is mainly used as a pain medication, and is also commonly used recreationally, or to make other illicit opioids. T ...

molecule just as the methyl group creates codeine and the ethyl group creates

ethylmorphine Ethylmorphine (also known as codethyline, dionine, and ethyl morphine) is an opioid analgesic and antitussive. Side effects Adverse effects are similar to other opioids and include drowsiness, constipation, vertigo, nausea, vomiting, and respira ...

or dionine (used as a generic name for that drug just as peronine is for benzylmorphine). It is about 90% as strong as codeine by weight. This drug, the benzyl ether of morphine, should not be confused with

dibenzoylmorphine Dibenzoylmorphine is an opiate analogue that is a derivative of morphine. It was developed in the early 1900s after first having been synthesised in 1875 in the UK by the CR Alders Wright organisation at Bayer, along with various other esters of ...

, an ester of morphine comparable to heroin. Another morphine ether developed around the same time, benzyldihydromorphine, saw some clinical use in the opening years of the 20th century. The ethers of morphine and codeine as well as dihydromorphine and dihydrocodeine number close to 100 and include such obscure opioids as formylallopseudoisocodeine. Benzylmorphine is used in much the same way as codeine and

, primarily as a moderate strength analgesic, for eye surgery as a 1 to 2% solution, and as a cough suppressant. It was available in the United States prior to 1914 and was still used until the 1960s, but fell into disuse once alternative opiate derivatives became preferred by doctors (i.e.

hydrocodone Hydrocodone, also known as dihydrocodeinone, is an opioid used to treat pain and as a cough suppressant. It is taken by mouth. Typically it is dispensed as the combination acetaminophen/hydrocodone or ibuprofen/hydrocodone for pain severe eno ...

as an analgesic and codeine as a cough suppressant) Benzylmorphine is now a Schedule I Controlled Substance in the US and is regulated internationally under UN drug conventions.Single Convention On Narcotic Drugs 1961 (United Nations) Benzylmorphine is an active metabolite of the opioid analgesic myrophine, formed in the liver. It has a metabolic fate similar to that of codeine. Benzylmorphine is used as the hydrochloride (free base conversion ratio 0.91) and methylsulphonate (0.80) and has a US DEA Administrative Controlled Substance Control Number of 9052.

Notes

References

* Merck Manual, 1900 * Merck Index, 1998
United States Department of Justice, Drug Enforcement Administration: Controlled Substances in Schedule I
{{Opioidergics Secondary alcohols 4,5-Epoxymorphinans Mu-opioid receptor agonists Opioids Phenol ethers Semisynthetic opioids Benzyl compounds