Acetylpropionylmorphine 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 ...

analogue that is an ester of

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 the early 1900s after first being synthesised in Great Britain in 1875 but shelved along with heroin and various other esters of morphine. Acetylpropionylmorphone was never used medically, instead being widely sold as one of the first "

designer drug 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. D ...

s" for around five years following the introduction of the first international restrictions on the sale of

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 ...

in 1925. It is described as being virtually identical to heroin and morphine in its effects, and consequently was itself banned internationally in 1930 by the Health Committee of the League of Nations, in order to prevent its sale as an unscheduled alternative to heroin.

Morphine ester chemistry

Another name for this drug is 3-acetyl-6-propionylmorphine, and it is produced by the acetylation of 6-propionylmorphine, an active opiate which is an ester of morphine first produced along with heroin and numerous other mono-, di-, and tetra-esters of morphine in the United Kingdom in 1874-1876 and then shelved; 6-propionylmorphine was later researched by firms and organisations in Italy, Austria, Germany, the US, the United Kingdom and elsewhere. Functional groups which are added to morphine and its esters to make active opioids include the benzoyl, acetyl, formyl, propionyl, butroyl, butyl, salicoyl, nicotinoyl, cinnamoyl, and others. It was discovered shortly after the development of

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.Rama Rao Nadendla. Principles Of Organic ...

(discovered in nature and/or first synthesised circa 1880, commercially available in 1900),

hydromorphone Hydromorphone, also known as dihydromorphinone, and sold under the brand name Dilaudid among others, is an opioid used to treat moderate to severe pain. Typically, long-term use is only recommended for pain due to cancer. It may be used by mou ...

(first synthesised 1924), and oxymorphone (synthesised 1914), that mono, di, tri, and perhaps tetra esters could be developed from them as well. A smaller number of 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 ...

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 ...

, and

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 1908 a ...

, and one or two of

oxycodone Oxycodone, sold under various brand names such as Roxicodone and OxyContin (which is the extended release form), is a strong, semi-synthetic opioid used medically for treatment of moderate to severe pain. It is highly addictive and a commonly ...

are also known and used in medicine.

References

Opioids 4,5-Epoxymorphinans Propionate esters Phenol esters Acetate esters Mu-opioid receptor agonists Semisynthetic opioids Cyclic ethers {{Analgesic-stub

Morphine ester chemistry

See also

References