Thebaine (paramorphine), also known as codeine methyl enol ether, 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 antagonis ...

alkaloid Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar ...

, its name coming from the

Greek Greek may refer to: Greece 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 ...

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

Upper Egypt Upper Egypt ( ar, صعيد مصر ', shortened to , , locally: ; ) is the southern portion of Egypt and is composed of the lands on both sides of the Nile that extend upriver from Lower Egypt in the north to Nubia in the south. In ancient ...

. A minor constituent of

opium Opium (or poppy tears, scientific name: ''Lachryma papaveris'') is dried latex obtained from the seed capsules of the opium poppy ''Papaver somniferum''. Approximately 12 percent of opium is made up of the analgesic alkaloid morphine, which i ...

, thebaine is chemically similar to both

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 ...

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 (, , US chiefly ) is a highly toxic, colorless, bitter, crystalline alkaloid used as a pesticide, particularly for killing small vertebrates such as birds and rodents. Strychnine, when inhaled, swallowed, or absorbed through the eye ...

poisoning. The synthetic

enantiomer In chemistry, an enantiomer ( /ɪˈnænti.əmər, ɛ-, -oʊ-/ ''ih-NAN-tee-ə-mər''; from Ancient Greek ἐνάντιος ''(enántios)'' 'opposite', and μέρος ''(méros)'' 'part') – also called optical isomer, antipode, or optical ant ...

(+)-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 l. Lalezari nature 213, 1244, 1967 doi:10.1038/2131244a0 ) is a sturdy hardy perennial poppy with large d ...

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

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 ...

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 ...

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 ...

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 beg ...

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, clammin ...

naloxone Naloxone, sold under the brand names Narcan (4 mg) and Kloxxado (8 mg) among others, is a medication used to reverse or reduce the effects of opioids. It is commonly used to counter decreased breathing in opioid overdose. Effects begin within ...

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

buprenorphine Buprenorphine 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 and subcutaneous), as a skin patch (transdermal), ...

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 r ...

. 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 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 United Nation ...

in the United Kingdom, is controlled as an analog of a Schedule II drug per the Analog Act in the United States, and is controlled with its derivatives and salts, as a Schedule I substance of the

Controlled Drugs and Substances Act The ''Controlled Drugs and Substances Act'' (french: Loi réglementant certaines drogues et autres substances) (the ''Act'') is Canada's federal drug control statute. Passed in 1996 under Prime Minister Jean Chrétien's government, it repeals ...

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 drug trafficking and distribution within th ...

(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 that is present in the morphinian alkaloid pathway of opium poppy. Its biosynthetic precursor is the alkaloid reticuline, (''R'')-reticuline. (''R'')-Reticuline is converted to salutaridine b ...

oripavine Oripavine is an opioid and the major metabolite of thebaine. It is the parent compound from which a series of semi-synthetic opioids are derived, which includes the compounds etorphine and buprenorphine. Although its analgesic potency is compar ...

and

reticuline Reticuline is a chemical compound found in a variety of plants including ''Lindera aggregata'', ''Annona squamosa'', and ''Ocotea fasciculata'' (also known as ''Ocotea duckei''). It is based on the benzylisoquinoline structure. Reticuline is one ...

. 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, minus the rip ...

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 ...

of 16 November 2022 reported that four batches of Hoyts brand poppy seeds were being recalled due to unusually high levels of thebaine, and that at least twelve people in

New South Wales ) , nickname = , image_map = New South Wales in Australia.svg , map_caption = Location of New South Wales in AustraliaCoordinates: , subdivision_type = Country , subdivision_name = Australia , established_title = Before federation , es ...

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

E. coli ''Escherichia coli'' (),Wells, J. C. (2000) Longman Pronunciation Dictionary. Harlow ngland Pearson Education Ltd. also known as ''E. coli'' (), is a Gram-negative, facultative anaerobic, rod-shaped, coliform bacterium of the genus ''Escher ...

References

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

Synthesis

Research

See also

References