Dipropanoylmorphine (Dipropionylmorphine in U.S. English) is an

opiate An opiate, in classical pharmacology, is a substance derived from opium. In more modern usage, the term '' opioid'' is used to designate all substances, both natural and synthetic, that bind to opioid receptors in the brain (including antagoni ...

derivative, the 3,6-dipropanoyl

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ...

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 ...

. It was developed in 1972 as an

analgesic An analgesic drug, also called simply an analgesic (American English), analgaesic (British English), pain reliever, or painkiller, is any member of the group of drugs used to achieve relief from pain (that is, analgesia or pain management). It ...

. It is rarely used in some countries for the relief of severe

pain Pain is a distressing feeling often caused by intense or damaging stimuli. The International Association for the Study of Pain defines pain as "an unpleasant sensory and emotional experience associated with, or resembling that associated with, ...

such as that caused by terminal

cancer Cancer is a group of diseases involving abnormal cell growth with the potential to invade or spread to other parts of the body. These contrast with benign tumors, which do not spread. Possible signs and symptoms include a lump, abnormal b ...

, as an alternative to

diamorphine Heroin, also known as diacetylmorphine and diamorphine among other names, is a potent opioid mainly used as a recreational drug for its euphoric effects. Medical grade diamorphine is used as a pure hydrochloride salt. Various white and brown ...

(heroin) and morphine. The drug was first synthesised circa or about 1875 in Great Britain along with many other esters of morphine, all of which were shelved at the time, some of which were later developed such as

heroin Heroin, also known as diacetylmorphine and diamorphine among other names, is a potent opioid mainly used as a recreational drug for its euphoric effects. Medical grade diamorphine is used as a pure hydrochloride salt. Various white and bro ...

(1898), acetylpropionylmorphine (1923),

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 ...

(1900 and/or 1924), and so on. The name of this drug is also given as 3,6-dipropanoylmorphine and its 6-mono-acetylated homologue is also a longer-acting heroin-like drug, as are 3,6-diformylmorphine and 6-formylmorphine. Dipropanoylmorphine, though rarely used, is considered to be a safer and less addictive alternative to

. Studies and clinical trials comparing dipropanoylmorphine to morphine have produced results that indicate the incidence of side-effects are far more common with morphine. Respiratory depression,

euphoria Euphoria ( ) is the experience (or affect) of pleasure or excitement and intense feelings of well-being and happiness. Certain natural rewards and social activities, such as aerobic exercise, laughter, listening to or making music and d ...

, excessive sedation and somnolence (so-called 'nodding' by recreational opioid users), constipation, miosis (pinpoint pupils), nausea,

bradycardia Bradycardia (also sinus bradycardia) is a slow resting heart rate, commonly under 60 beats per minute (BPM) as determined by an electrocardiogram. It is considered to be a normal heart rate during sleep, in young and healthy or elderly adults, ...

, behavioral disturbances, and severe physical and psychological dependence on morphine is more likely with the use of morphine versus dipropanoylmorphine. Dipropanoylmorphine is slightly slower acting than diamorphine and morphine, but longer lasting, and is slightly more potent by weight due to its higher lipophilicity. Side effects are generally relatively mild for an opioid with a similar profile to morphine/heroin and typical of other

opioids Opioids are substances that act on opioid receptors to produce morphine-like effects. Medically they are primarily used for pain relief, including anesthesia. Other medical uses include suppression of diarrhea, replacement therapy for opioid u ...

. The most common side effects associated with dipropanoylmorphine are

itching Itch (also known as pruritus) is a sensation that causes the desire or reflex to scratch. Itch has resisted many attempts to be classified as any one type of sensory experience. Itch has many similarities to pain, and while both are unpleasan ...

nausea Nausea is a diffuse sensation of unease and discomfort, sometimes perceived as an urge to vomit. While not painful, it can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of th ...

and

respiratory depression Hypoventilation (also known as respiratory depression) occurs when ventilation is inadequate (''hypo'' meaning "below") to perform needed respiratory gas exchange. By definition it causes an increased concentration of carbon dioxide (hypercapni ...

. Dipropanoylmorphine is prepared by reacting morphine with

propionic anhydride Propionic anhydride is an organic compound with the formula (CH3CH2CO)2O. This simple acid anhydride is a colourless liquid. It is a widely used reagent in organic synthesis as well as for producing specialty derivatives of cellulose. Synthesis ...

, in an analogous manner to how heroin is produced by reacting morphine with

acetic anhydride Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a co ...

. While

is a restricted chemical around the world due to its potential uses in making heroin from morphine for the illicit market, it is used in vast amounts by the chemical industry for the manufacture of drugs such as

aspirin Aspirin, also known as acetylsalicylic acid (ASA), is a nonsteroidal anti-inflammatory drug (NSAID) used to reduce pain, fever, and/or inflammation, and as an antithrombotic. Specific inflammatory conditions which aspirin is used to treat inc ...

. Propanoic anhydride however is much less widely used. Although it is used in the manufacture of a range of pharmaceuticals, none of these are produced in nearly as large quantities, and sales of propanoic anhydride in quantities larger than one gram must be reported in many countries because of its potential use in making

fentanyl Fentanyl, also spelled fentanil, is a very potent synthetic opioid used as a pain medication. Together with other drugs, fentanyl is used for anesthesia. It is also used illicitly as a recreational drug, sometimes mixed with heroin, cocain ...

type synthetic opiates.

References

{{Opioidergics Opioids 4,5-Epoxymorphinans Mu-opioid receptor agonists Propionate esters Semisynthetic opioids