Acetorphine

Last updated
Acetorphine
Acetorphine structure.svg
Acetorphine 3D BS.png
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • 4,5α-epoxy-7α-(1-hydroxy-1-methylbutyl)-6-methoxy-17-methyl-6,14-endo-ethenomorphinan-3-yl acetate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard 100.291.523 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C27H35NO5
Molar mass 453.579 g·mol−1
3D model (JSmol)
  • C[C@@](O)(CCC)[C@H]6C[C@]43/C=C/[C@]6(OC)[C@@H]1Oc5c2c(C[C@H]4N(C)CC[C@@]123)ccc5OC(C)=O
  • InChI=1S/C27H35NO5/c1-6-9-24(3,30)19-15-25-10-11-27(19,31-5)23-26(25)12-13-28(4)20(25)14-17-7-8-18(32-16(2)29)22(33-23)21(17)26/h7-8,10-11,19-20,23,30H,6,9,12-15H2,1-5H3/t19-,20-,23-,24-,25-,26+,27-/m1/s1 Yes check.svgY
  • Key:LFYBMMHFJIAKFE-PMEKXCSPSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Acetorphine is a potent opioid analgesic, up to 8700 times stronger than morphine by weight. [1] It is a derivative of the more well-known opioid etorphine, which is used as a very potent veterinary painkiller and anesthetic medication, primarily for the sedation of large animals such as elephants, giraffes and rhinos.

Contents

Acetorphine was developed in 1966 by the Reckitt research group that developed etorphine. Acetorphine was developed for the same purpose as etorphine itself, namely as a strong tranquilizer for use in immobilizing large animals in veterinary medicine. Despite showing some advantages over etorphine, for instance producing less toxic side effects in giraffes, [2] acetorphine was never widely adopted for veterinary use, and etorphine (along with other tranquilizers such as carfentanil and azaperone) remains the drug of choice in this application.

Australia

Acetorphine is a schedule 9 substance in Australia under the Poisons Standard (February 2017). [3] A schedule 9 drug is outlined in the Poisons Act 1964 as "Substances which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of the CEO." [4]

Under the Misuse of Drugs Act 1981 6.0 g is the amount required determining a court of trial, 2.0 g is considered intent to sell and supply. [5]

Germany

Acetorphine is illegal in Germany (Anlage I).

United Kingdom

Acetorphine is considered a Class A drug by the UK Misuse of Drugs Act since 1971, making its unlawful possession and distribution illegal. Class A drugs are deemed to be the most dangerous.

United States

Acetorphine is a Schedule I controlled substance in the United States. Its DEA Administrative Controlled Substances Control Number is 9319 and the one salt in use, acetorphine hydrochloride, has a freebase conversion ratio of 0.93.

Italy

In Italy acetorphine is illegal, as are the parent compounds etorphine and dihydroetorphine. [6]

See also

Related Research Articles

<span class="mw-page-title-main">Controlled Substances Act</span> United States drug-regulating law

The Controlled Substances Act (CSA) is the statute establishing federal U.S. drug policy under which the manufacture, importation, possession, use, and distribution of certain substances is regulated. It was passed by the 91st United States Congress as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970 and signed into law by President Richard Nixon. The Act also served as the national implementing legislation for the Single Convention on Narcotic Drugs.

<span class="mw-page-title-main">Oxycodone</span> Opioid medication

Oxycodone, sold under various brand names such as Roxicodone and OxyContin, is a semi-synthetic opioid used medically for treatment of moderate to severe pain. It is highly addictive and is a commonly abused drug. It is usually taken by mouth, and is available in immediate-release and controlled-release formulations. Onset of pain relief typically begins within fifteen minutes and lasts for up to six hours with the immediate-release formulation. In the United Kingdom, it is available by injection. Combination products are also available with paracetamol (acetaminophen), ibuprofen, naloxone, naltrexone, and aspirin.

<span class="mw-page-title-main">Thebaine</span> Opiate alkaloid constituent of opium

Thebaine (paramorphine), also known as codeine methyl enol ether, is an opiate alkaloid, its name coming from the Greek Θῆβαι, Thēbai (Thebes), an ancient city in Upper Egypt. A minor constituent of opium, thebaine is chemically similar to both morphine and codeine, but has stimulatory rather than depressant effects. At high doses, it causes convulsions similar to strychnine poisoning. The synthetic enantiomer (+)-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 and can be converted industrially into a variety of compounds, including hydrocodone, hydromorphone, oxycodone, oxymorphone, nalbuphine, naloxone, naltrexone, buprenorphine, butorphanol and etorphine.

<span class="mw-page-title-main">Carfentanil</span> Synthetic opioid analgesic

Carfentanil or carfentanyl, sold under the brand name Wildnil, is an extremely potent opioid analgesic which is used in veterinary medicine to anesthetize large animals such as elephants and rhinoceroses. It is typically administered in this context by tranquilizer dart. Carfentanil has also been used in humans for imaging of opioid receptors. It has additionally been used as a recreational drug, typically by injection, insufflation, or inhalation. Deaths have been reported in association with carfentanil.

<span class="mw-page-title-main">Dihydrocodeine</span> Opioid

Dihydrocodeine is a semi-synthetic opioid analgesic prescribed for pain or severe dyspnea, or as an antitussive, either alone or compounded with paracetamol (acetaminophen) or aspirin. It was developed in Germany in 1908 and first marketed in 1911.

<span class="mw-page-title-main">Etorphine</span> Semi-synthetic opioid

Etorphine (M99) is a semi-synthetic opioid possessing an analgesic potency approximately 10,000–30,000 times that of morphine. It was first prepared in 1960 from oripavine, which does not generally occur in opium poppy extract but rather the related plants Papaver orientale and Papaver bracteatum. It was later reproduced in 1963 by a research group at MacFarlan Smith in Gorgie, Edinburgh, led by Kenneth Bentley. It can also be produced from thebaine.

<span class="mw-page-title-main">Nalbuphine</span> Opioid analgesic

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.

<span class="mw-page-title-main">Morphinan</span> Chemical compound

Morphinan is the prototype chemical structure of a large chemical class of psychoactive drugs, consisting of opiate analgesics, cough suppressants, and dissociative hallucinogens, among others. Typical examples include compounds such as morphine, codeine, and dextromethorphan (DXM). Despite related molecular structures, the pharmacological profiles and mechanisms of action between the various types of morphinan substances can vary substantially. They tend to function either as μ-opioid receptor agonists (opioids), or NMDA receptor antagonists (dissociatives).

<span class="mw-page-title-main">Codeine</span> Opiate and prodrug of morphine used to treat pain

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 used to treat mild to moderate degrees of pain. Greater benefit may occur when combined with paracetamol (acetaminophen) or a nonsteroidal anti-inflammatory drug (NSAID) such as aspirin or ibuprofen. Evidence does not support its use for acute cough suppression in children or adults. In Europe, it is not recommended as a cough medicine in those under 12 years of age. It is generally taken by mouth. It typically starts working after half an hour, with maximum effect at two hours. Its effects last for about four to six hours. Codeine exhibits abuse potential similar to other opioid medications, including a risk of habituation and overdose.

<span class="mw-page-title-main">Diprenorphine</span> Chemical compound

Diprenorphine, also known as diprenorfin, is a non-selective, high-affinity, weak partial agonist of the μ- (MOR), κ- (KOR), and δ-opioid receptor (DOR) which is used in veterinary medicine as an opioid antagonist. It is used to reverse the effects of super-potent opioid analgesics such as etorphine and carfentanil that are used for tranquilizing large animals. The drug is not approved for use in humans.

<span class="mw-page-title-main">Dihydroetorphine</span> Opioid analgesic drug

Dihydroetorphine was developed by K. W. Bentley at McFarlan-Smith in the 1960s and is a potent opioid analgesic used mainly in China. It is a derivative of the better-known opioid etorphine, a very potent veterinary painkiller and anesthetic medication used primarily for the sedation of large animals such as elephants, giraffes, and rhinos.

<span class="mw-page-title-main">Oripavine</span> Chemical compound

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 comparable to morphine, it is not used clinically due to its severe toxicity and low therapeutic index. Due to its use in manufacture of strong opioids, oripavine is a controlled substance in some jurisdictions.

<span class="mw-page-title-main">Tapentadol</span> Opioid analgesic of benzenoid class

Tapentadol, brand names Nucynta among others, is a centrally acting opioid analgesic of the benzenoid class with a dual mode of action as an agonist of the μ-opioid receptor and as a norepinephrine reuptake inhibitor (NRI). Analgesia occurs within 32 minutes of oral administration, and lasts for 4–6 hours.

<span class="mw-page-title-main">Cyprenorphine</span> Chemical compound

Cyprenorphine (M285), N-cyclo-propylmethyl-6,14-endoetheno-7α-(1-hydroxy-1-methylethyl)-6,7,8,14-tetrahydronororipavine, is an opioid drug. It is related to more well-known opioids such as buprenorphine, which is used as an analgesic and for the treatment of opioid addiction, and diprenorphine, which is used as an antidote to reverse the effects of other opioids. It is roughly 35 times as strong as nalorphine.

<span class="mw-page-title-main">Allylprodine</span> Opioid analgesic drug

Allylprodine is an opioid analgesic that is an analog of prodine. It was discovered by Hoffman-La Roche in 1957 during research into the related drug pethidine. Derivatives were tested to prove the theory that phenolic and non-phenolic opioids bind at different sites of the opiate receptor.

<span class="mw-page-title-main">Phenazocine</span> Opioid analgesic

Phenazocine is an opioid analgesic drug, which is related to pentazocine and has a similar profile of effects.

<span class="mw-page-title-main">7-PET</span> Chemical compound

7-PET is an opioid analgesic drug that has 300 times the potency of morphine by weight. It was discovered by K.W. Bentley and is related to the more well known oripavine derivative etorphine, which is used as a veterinary painkiller and anesthetic medication for the sedation of large animals such as elephants, giraffes, and rhinos. 7-PET itself has a 3-O-methyl ether which reduces potency, but the 3-OH derivative is around 2200 times more potent than morphine, almost the same potency as etorphine as a μ agonist, and unexpectedly the 3-hydrogen compound is also around the same potency of 2000 times morphine.

<span class="mw-page-title-main">Benzethidine</span> Chemical compound

Benzethidine is a 4-phenylpiperidine derivative that is related to the clinically used opioid analgesic drug pethidine.

<span class="mw-page-title-main">AH-7921</span> Opioid analgesic

AH-7921 is an opioid analgesic drug selective for the μ-opioid receptor, having around 90% the potency of morphine when administered orally. It was discovered in the 1970s by a team at Allen and Hanburys located in the United Kingdom. The drug is considered a new psychoactive substance (NPS) in which it is synthetically created in laboratories to mimic that of controlled substances. The substance has also been sold on the internet since 2012 as a "research chemical". When sold online it may be called the alternative name doxylam, not to be confused with doxylamine. AH-7921 has never progressed to clinical trials. The DEA is not aware of any medical usage in the United States, and has not insisted the Health and Human Services department (HHS) to conduct any medical research of the substance's uses.

<span class="mw-page-title-main">MT-45</span> Chemical compound

MT-45 (IC-6) is an opioid analgesic drug invented in the 1970s by Dainippon Pharmaceutical Co. It is chemically a 1-substituted-4-(1,2-diphenylethyl) piperazine derivative, which is structurally unrelated to most other opioid drugs. Racemic MT-45 has around 80% the potency of morphine, with almost all opioid activity residing in the (S) enantiomer. It has been used as a lead compound from which a large family of potent opioid drugs have been developed, including full agonists, partial agonists, and antagonists at the three main opioid receptor subtypes. Fluorinated derivatives of MT-45 such as 2F-MT-45 are significantly more potent as μ-opioid receptor agonists, and one of its main metabolites 1,2-diphenylethylpiperazine also blocks NMDA receptors.

References

  1. Bentley KW, Hardy DG (June 1967). "Novel analgesics and molecular rearrangements in the morphine-thebaine group. 3. Alcohols of the 6,14-endo-ethenotetrahydrooripavine series and derived analogs of N-allylnormorphine and -norcodeine". Journal of the American Chemical Society. 89 (13): 3281–92. doi:10.1021/ja00989a032. PMID   6042764.
  2. "The case of etorphine and acetorphine". Bulletin on Narcotics. UNODC. 1968 (2): 51–52. 1968.
  3. "Poisons Standard". Federal Register of Legislation. Australian Government. October 2015.
  4. "Poisons Act" (PDF). Western Australia. 1964. Archived from the original (PDF) on 2015-12-22.
  5. "Misuse of Drugs Act" (PDF). Western Australia. 1981. Archived from the original (PDF) on 2015-12-22.
  6. Salute, Ministero della. "Tabelle delle sostanze stupefacenti e psicotrope". www.salute.gov.it (in Italian). Retrieved 2022-04-09.