Morphine-''N''-oxide (genomorphine) is an active

opioid 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 us ...

metabolite 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 analgesic, pain medication, and is also commonly used recreational drug, recreationally, or to make ...

. Morphine itself, in trials with rats, is 11–22 times more potent than morphine-''N''-oxide subcutaneously and 39–89 times more potent

intraperitoneally Intraperitoneal injection or IP injection is the injection of a substance into the peritoneum (body cavity). It is more often applied to animals than to humans. In general, it is preferred when large amounts of blood replacement fluids are needed ...

. However, pretreatment with

amiphenazole Amiphenazole (Daptazile) is a respiratory stimulant traditionally used as an antidote for barbiturate or opiate overdose, usually in combination with bemegride, as well as poisoning from other sedative drugs and treatment of respiratory failure ...

tacrine Tacrine is a centrally acting acetylcholinesterase inhibitor and indirect cholinergic agonist (parasympathomimetic). It was the first centrally acting cholinesterase inhibitor approved for the treatment of Alzheimer's disease, and was marketed un ...

increases the potency of morphine-''N''-oxide in relation to morphine (intraperitoneally more so than in subcutaneous administration). A possible explanation is that morphine-''N''-oxide is rapidly inactivated in the liver and impairment of inactivation processes or enzymes increases functionality. Morphine-''N''-oxide can also form as a decomposition product of morphine outside the body and may show up in assays of opium and

poppy straw concentrate Poppy straw (also known as opium straw, mowed opium straw, crushed poppy capsule, poppy chaff, or poppy husk) is derived from opium poppies (''Papaver somniferum'') that are harvested when fully mature and dried by mechanical means, minus the ri ...

. Codeine and the semi-synthetics 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 brow ...

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 an ...

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 ...

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 ...

, and

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 en ...

also have equivalent

amine oxide In chemistry, an amine oxide, also known as an amine ''N''-oxide or simply ''N''-oxide, is a chemical compound that contains the functional group , a nitrogen-oxygen coordinate covalent bond with three additional hydrogen and/or substituent-grou ...

derivatives The derivative of a function is the rate of change of the function's output relative to its input value. Derivative may also refer to: In mathematics and economics * Brzozowski derivative in the theory of formal languages * Formal derivative, an ...

. Morphine-''N''-Oxide has a DEA

ACSCN Administrative Controlled Substances Code Number (ACSCN) is a number assigned to drugs listed on the schedules created by the US Controlled Substances Act (CSA). The ACSCN is defined in 21 CFR § 1308.03(a). Each chemical/drug on one of the schedu ...

of 9307 and annual production quota of 655 grams in 2013. It is a Schedule I controlled substance in the US.http://www.deadiversion.usdoj.gov/fed_regs/quotas/2013/fr0620.htm

References

4,5-Epoxymorphinans Opioid metabolites Phenols Mu-opioid receptor agonists Amine oxides {{analgesic-stub

See also

References