Dipropanoylmorphine
Encyclopedia
Dipropanoylmorphine is an opiate
derivative, the 3,6-dipropanoyl ester
of morphine
. It was developed in 1974 as an analgesic
. It is rarely used in some countries for the relief of severe pain
such as that caused by terminal cancer
, as an alternative to diamorphine (heroin) and morphine.
Dipropanoylmorphine, though rarely used, is considered to be a safer and less addictive alternative to morphine
. 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
, excessive sedation and somnolence (so-called 'nodding' by opiate abusers), constipation, miosis
(pinpoint pupils), nausea, bradycardia
, 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. The most common side effects associated with dipropanoylmorphine are itching, nausea
and respiratory depression.
Dipropanoylmorphine is prepared by reacting morphine with propionic anhydride, in an analogous manner to how heroin is produced by reacting morphine with acetic anhydride
.
While acetic anhydride
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
. 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 type synthetic opiates.
Opiate
In medicine, the term opiate describes any of the narcotic opioid alkaloids found as natural products in the opium poppy plant.-Overview:Opiates are so named because they are constituents or derivatives of constituents found in opium, which is processed from the latex sap of the opium poppy,...
derivative, the 3,6-dipropanoyl ester
Ester
Esters are chemical compounds derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol. Esters are usually derived from an inorganic acid or organic acid in which at least one -OH group is replaced by an -O-alkyl group, and most commonly from carboxylic acids and...
of morphine
Morphine
Morphine is a potent opiate analgesic medication and is considered to be the prototypical opioid. It was first isolated in 1804 by Friedrich Sertürner, first distributed by same in 1817, and first commercially sold by Merck in 1827, which at the time was a single small chemists' shop. It was more...
. It was developed in 1974 as an analgesic
Analgesic
An analgesic is any member of the group of drugs used to relieve pain . The word analgesic derives from Greek an- and algos ....
. It is rarely used in some countries for the relief of severe pain
Pain
Pain is an unpleasant sensation often caused by intense or damaging stimuli such as stubbing a toe, burning a finger, putting iodine on a cut, and bumping the "funny bone."...
such as that caused by terminal cancer
Cancer
Cancer , known medically as a malignant neoplasm, is a large group of different diseases, all involving unregulated cell growth. In cancer, cells divide and grow uncontrollably, forming malignant tumors, and invade nearby parts of the body. The cancer may also spread to more distant parts of the...
, as an alternative to diamorphine (heroin) and morphine.
Dipropanoylmorphine, though rarely used, is considered to be a safer and less addictive alternative to morphine
Morphine
Morphine is a potent opiate analgesic medication and is considered to be the prototypical opioid. It was first isolated in 1804 by Friedrich Sertürner, first distributed by same in 1817, and first commercially sold by Merck in 1827, which at the time was a single small chemists' shop. It was more...
. 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
Euphoria is an emotional and mental state defined as a sense of great elation and well being.Euphoria may also refer to:* Euphoria , a genus of scarab beetles* Euphoria, a genus name previously used for the longan and other trees...
, excessive sedation and somnolence (so-called 'nodding' by opiate abusers), constipation, miosis
Miosis
Miosis is the constriction of the pupil of the eye to two millimeters or less...
(pinpoint pupils), nausea, bradycardia
Bradycardia
Bradycardia , in the context of adult medicine, is the resting heart rate of under 60 beats per minute, though it is seldom symptomatic until the rate drops below 50 beat/min. It may cause cardiac arrest in some patients, because those with bradycardia may not be pumping enough oxygen to their heart...
, 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. The most common side effects associated with dipropanoylmorphine are itching, nausea
Nausea
Nausea , is a sensation of unease and discomfort in the upper stomach with an involuntary urge to vomit. It often, but not always, precedes vomiting...
and respiratory depression.
Dipropanoylmorphine is prepared by reacting morphine with propionic anhydride, in an analogous manner to how heroin is produced by reacting morphine with acetic anhydride
Acetic anhydride
Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula 2O. Commonly abbreviated Ac2O, it is the simplest isolatable acid anhydride and is a widely used reagent in organic synthesis...
.
While acetic anhydride
Acetic anhydride
Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula 2O. Commonly abbreviated Ac2O, it is the simplest isolatable acid anhydride and is a widely used reagent in organic synthesis...
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
Aspirin , also known as acetylsalicylic acid , is a salicylate drug, often used as an analgesic to relieve minor aches and pains, as an antipyretic to reduce fever, and as an anti-inflammatory medication. It was discovered by Arthur Eichengrun, a chemist with the German company Bayer...
. 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 type synthetic opiates.