Dibutyrylmorphine (also known as dibutanoylmorphine) is the 3,6-dibutyryl

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

morphine Morphine, formerly also called morphia, is an opiate that is found naturally in opium, a dark brown resin produced by drying the latex of opium poppies (''Papaver somniferum''). It is mainly used as an analgesic (pain medication). There are ...

, first synthesized by the CR Alders Wright organization in the United Kingdom in 1875. In animal studies its potency as an

analgesic An analgesic drug, also called simply an analgesic, antalgic, pain reliever, or painkiller, is any member of the group of drugs used for pain management. Analgesics are conceptually distinct from anesthetics, which temporarily reduce, and in s ...

is higher compared to morphine, but lower than that of heroin. Its structure is similar to that of other morphine esters such as

heroin Heroin, also known as diacetylmorphine and diamorphine among other names, is a morphinan opioid substance synthesized from the Opium, dried latex of the Papaver somniferum, opium poppy; it is mainly used as a recreational drug for its eupho ...

and

nicomorphine 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, a ...

. In many countries it is controlled as an ester of a controlled substance. Esters of morphine were first produced by boiling morphine in acids or

acid anhydride An acid anhydride is a type of chemical compound derived by the removal of water molecules from an acid. In organic chemistry, organic acid anhydrides contain the functional group . Organic acid anhydrides often form when one equivalent of wa ...

s including acetic, formic, propanoic, benzoic, butyric, and others, forming numerous mono-, di-, and tetraesters. Some of these were later researched further by others and some were eventually marketed. They included heroin, the first

designer drugs A designer drug is a structural or functional analog of a controlled substance that has been designed to mimic the pharmacological effects of the original drug, while avoiding classification as illegal and/or detection in standard drug tests. ...

which were produced in the late 1920s to replace heroin when it was outlawed by the League of Nations, medicinal drugs such as

and others. Some of the corresponding esters of

codeine Codeine is an opiate and prodrug of morphine mainly used to treat pain, coughing, and diarrhea. It is also commonly used as a recreational drug. It is found naturally in the sap of the opium poppy, ''Papaver somniferum''. It is typically use ...

dihydrocodeine Dihydrocodeine is a semi- synthetic opioid analgesic prescribed for pain or severe dyspnea, or as an antitussive, either alone or compounded with paracetamol (acetaminophen) (as in co-dydramol) or aspirin. It was developed in Germany in 190 ...

dihydromorphine Dihydromorphine (Paramorfan, Paramorphan) is a semi-synthetic opioid structurally related to and derived from morphine. The 7,8-double bond in morphine is reduced to a single bond to get dihydromorphine. Dihydromorphine is a moderately strong a ...

isocodeine Isocodeine is an opioid research chemical related to codeine. It is an epimer of codeine that can be prepared from codeine via a Mitsunobu reaction The Mitsunobu reaction is an organic reaction that converts an alcohol into a variety of funct ...

were also developed, such as the cough suppressant

nicocodeine Nicocodeine (Lyopect, Tusscodin) is an opioid analgesic and cough suppressant, an ester of codeine closely related to dihydrocodeine and the codeine analogue of nicomorphine. It is not commonly used in most countries, but has activity similar t ...

.Esters of Morphine
United Nations Office of Drug and Crime 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.

References

{{Opioidergics 4,5-Epoxymorphinans Euphoriants Morphine Mu-opioid receptor agonists Opioids Catechol ethers Prodrugs Semisynthetic opioids