Thebaine (paramorphine), also known as codeine methyl enol ether, is an

opiate An opiate is an alkaloid substance derived from opium (or poppy straw). It differs from the similar term ''opioid'' in that the latter is used to designate all substances, both natural and synthetic, that bind to opioid receptors in the brain ( ...

alkaloid Alkaloids are a broad class of natural product, naturally occurring organic compounds that contain at least one nitrogen atom. Some synthetic compounds of similar structure may also be termed alkaloids. Alkaloids are produced by a large varie ...

, its name coming from the

Greek Greek may refer to: Anything of, from, or related to Greece, a country in Southern Europe: *Greeks, an ethnic group *Greek language, a branch of the Indo-European language family **Proto-Greek language, the assumed last common ancestor of all kno ...

Θῆβαι, '' Thēbai'' (Thebes), an ancient city in

Upper Egypt Upper Egypt ( ', shortened to , , locally: ) is the southern portion of Egypt and is composed of the Nile River valley south of the delta and the 30th parallel North. It thus consists of the entire Nile River valley from Cairo south to Lake N ...

. A minor constituent of

opium Opium (also known as poppy tears, or Lachryma papaveris) is the dried latex obtained from the seed Capsule (fruit), capsules of the opium poppy ''Papaver somniferum''. Approximately 12 percent of opium is made up of the analgesic alkaloid mor ...

, thebaine is chemically similar to both

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 ...

and

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 ...

, but has stimulatory rather than depressant effects. At high doses, it causes convulsions similar to

strychnine Strychnine (, , American English, US chiefly ) is a highly toxicity, toxic, colorless, bitter, crystalline alkaloid used as a pesticide, particularly for killing small vertebrates such as birds and rodents. Strychnine, when inhaled, swallowed, ...

poisoning. The synthetic

enantiomer In chemistry, an enantiomer (Help:IPA/English, /ɪˈnænti.əmər, ɛ-, -oʊ-/ Help:Pronunciation respelling key, ''ih-NAN-tee-ə-mər''), also known as an optical isomer, antipode, or optical antipode, is one of a pair of molecular entities whi ...

(+)-thebaine does show analgesic effects apparently mediated through opioid receptors, unlike the inactive natural enantiomer (−)-thebaine. While thebaine is not used therapeutically, it is the main alkaloid extracted from ''

Papaver bracteatum ''Papaver bracteatum'', also known as the Iranian poppy or Persian poppy and the great scarlet poppy (first described by Dr. N. Saharghi and Iraj Lalezari ''Nature'' 213, 1244, 1967 doi:10.1038/2131244a0 ) is a sturdy hardy perennial poppy with ...

'' (Iranian opium / Persian poppy) and can be converted industrially into a variety of compounds, including

hydrocodone Hydrocodone, also known as dihydrocodeinone, is a semi-synthetic 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 fo ...

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

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

oxymorphone Oxymorphone (sold under the brand names Numorphan and Opana among others) is a highly potent opioid analgesic indicated for treatment of severe pain. Pain relief after injection begins after about 5–10 minutes; after oral administration it ...

nalbuphine Nalbuphine, sold under the brand names Nubain among others, is an opioid analgesic which is used in the treatment of pain. It is given by injection into a vein, muscle, or fat. Side effects of nalbuphine include sedation, sweatiness, clam ...

naloxone Naloxone, sold under the brand name Narcan among others, is an opioid antagonist, a medication used to reverse or reduce the effects of opioids. For example, it is used to restore breathing after an opioid overdose. Effects begin within two ...

naltrexone Naltrexone, sold under the brand name Revia among others, is a medication primarily used to manage alcohol use or opioid use disorder by reducing cravings and feelings of euphoria associated with substance use disorder. It has also been ...

buprenorphine Buprenorphine, sold under the brand name Subutex among others, is an opioid used to treat opioid use disorder, acute pain, and chronic pain. It can be used under the tongue (sublingual), in the cheek (buccal), by injection (intravenous a ...

butorphanol Butorphanol is a morphinan-type synthetic agonist–antagonist opioid analgesic developed by Bristol-Myers. Butorphanol is most closely structurally related to levorphanol. Butorphanol is available as the tartrate salt in injectable, tablet, and ...

and

etorphine Etorphine (M99) is a semi-synthetic opioid possessing an analgesic potency approximately 1,000–3,000 times that of morphine. It was first prepared in 1960 from oripavine, which does not generally occur in opium poppy extract but rather the re ...

. Thebaine is controlled under international law, is listed as a Class A drug under the

Misuse of Drugs Act 1971 The Misuse of Drugs Act 1971 (c. 38) is an act of the Parliament of the United Kingdom. It represents action in line with treaty commitments under the Single Convention on Narcotic Drugs, the Convention on Psychotropic Substances, and the ...

in the United Kingdom, is controlled as an analog of a Schedule II drug per the

Analog Act The Federal Analogue Act, , is a section of the United States Controlled Substances Act passed in 1986 which allows any chemical "substantially similar" to a controlled substance listed in Schedule I or II to be treated as if it were listed ...

in the United States, and is controlled with its derivatives and salts, as a Schedule I substance of the

Controlled Drugs and Substances Act Control may refer to: Basic meanings Economics and business * Control (management), an element of management * Control, an element of management accounting * Comptroller (or controller), a senior financial officer in an organization * Controll ...

in Canada. The 2013 US

Drug Enforcement Administration The Drug Enforcement Administration (DEA) is a Federal law enforcement in the United States, United States federal law enforcement agency under the U.S. Department of Justice tasked with combating illicit Illegal drug trade, drug trafficking a ...

(DEA) aggregate manufacturing quota for thebaine (ACSCN 9333) was unchanged from the previous year at 145 metric tons. This alkaloid is biosynthetically related to

salutaridine Salutaridine, also known as floripavine, is an alkaloid Alkaloids are a broad class of natural product, naturally occurring organic compounds that contain at least one nitrogen atom. Some synthetic compounds of similar structure may also be ...

oripavine Oripavine is an opioid and the major metabolite of thebaine. It is the precursor to the semi-synthetic compounds etorphine and buprenorphine. Although this chemical compound has analgesic potency comparable to morphine, it is not used clinica ...

and

reticuline Reticuline is an alkaloid found in opium and a variety of plants including ''Lindera aggregata'', ''Annona squamosa'', and ''Ocotea#Selected species, Ocotea fasciculata'' (also known as ''Ocotea duckei''). Experiments in rodents suggest reticuli ...

. In 2012 there was an amounted 146,000 kilograms of thebaine produced. In 2013, Australia was the main producer of

poppy straw 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. Opium poppy s ...

rich in thebaine, followed by Spain and then France. By 2017, worldwide thebaine production dropped to 2,008 kg. Together, those three countries accounted for about 99 per cent of global production of such poppy straw. The

seed capsules are the primary source of thebaine, with the stem additionally yielding a significant amount.

The Canberra Times ''The Canberra Times'' is a daily newspaper in Canberra, Australia, which is published by Australian Community Media. It was founded in 1926, and has changed ownership and format several times. History ''The Canberra Times'' was launched in 1 ...

of 16 November 2022 reported that four batches of Hoyts brand

poppy seeds Poppy seed is an oilseed obtained from the poppy plant (''Papaver somniferum''). The tiny, kidney-shaped seeds have been harvested from dried seed pods by various civilizations for thousands of years. It is still widely used in many countries ...

were being recalled due to unusually high levels of thebaine, and that at least twelve people in

New South Wales New South Wales (commonly abbreviated as NSW) is a States and territories of Australia, state on the Eastern states of Australia, east coast of :Australia. It borders Queensland to the north, Victoria (state), Victoria to the south, and South ...

had required medical attention after ingesting them. As of 15 November 2022,

Food Standards Australia New Zealand Food Standards Australia New Zealand (FSANZ) (Māori: ''Te Mana Kounga Kai – Ahitereiria me Aotearoa''), formerly Australia New Zealand Food Authority (ANZFA), is the statutory authority in the Australian Government Health portfolio that is ...

(FSANZ) is coordinating a national recall of a number of poppy seed products due to the potential presence of thebaine.

Synthesis

Research

Thebaine has been produced by

GMO A genetically modified organism (GMO) is any organism whose genetic material has been altered using genetic engineering techniques. The exact definition of a genetically modified organism and what constitutes genetic engineering varies, with ...

E. coli ''Escherichia coli'' ( )Wells, J. C. (2000) Longman Pronunciation Dictionary. Harlow ngland Pearson Education Ltd. is a gram-negative, facultative anaerobic, rod-shaped, coliform bacterium of the genus ''Escherichia'' that is commonly foun ...

References

{{Authority control 4,5-Epoxymorphinans Ethers Natural opium alkaloids Cyclohexadienes Glycine receptor antagonists Opiates Convulsants Enol ethers

Synthesis

Research

See also

References