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Cyprenorphine[edit]

Rpulumo/sandbox
Cyprenorphine structure.svg
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
Formula C26H33NO4
Molar mass 423.545 g/mol
3D model (JSmol)
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Introduction[edit]

Cyprenorphine (M285), N-cyclo-propylmethyl-6,14-endoetheno-7α-(1-hydroxy-1-methylethyl)-6,7,8,14-tetrahydronororipavine, is a powerful antagonist of opioid receptors[1] and a highly potent specific antagonist [2] It blocks the binding of morphine and etorphine to these receptors[3] . Cyprenorphine is a drug which is an opioid derivative. 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[4] Cyprenorphine has mixed agonist-antagonist effects at opioid receptors, like those of buprenorphine. However the effects of cyprenorphine are somewhat different, as it produces pronounced dysphoric and hallucinogenic effects which limit its potential use as an analgesic.[5][6]


Medical Uses[edit]

Cyprenorphine increases locomotor activity[7] . It is normally used to reverse the clinically immobilizing effects of etorphine. These effects are reversed rapidly and almost entirely. Etorphine is a chemical relative of morphine, with similar analgesic characteristics but fewer side effects. For instance, in order to handle polar bears and other large animals, they are immobilized using etorphine and the effects of etorphine reversed as soon as handling is complete using cyprenorphine[8] . Etorphine and cyprenorphine come as white powders in a package and cannot be purchased separately. Both are administered by injection after dissolving in saline[9] . Because etorphine is used to immobilize large, still moving, animals, it is often administered intramuscularly using a dart whereas cyprenorphine can be administered intravenously in the femoral vein of the immobile animal[10]. Unlike other antagonists, used to reverse the effects of etorphine, the dose of cyprenorphine administered depends on the initial dose of etorphine instead of the weight of the animal. The recommended dose of cyprenorphine is three times that of the initial etrophine administered. Although the effects of cyprenorphine typically take from 40 – 60 seconds to kick in, it has been observed to take up to 3 hours in white rhinoceroses [11].

Adverse Effects[edit]

Cyprenorphine induces depression over an hour in rats[12] . It has also been found to induce psychotomimetic actions in humans[13] and dysphoria when used as a post-operative analgesic in patients[14] . Because of these side effects, it is seldom used in humans, with diprenorphine preferred instead.

Mechanism of action[edit]

Although it is still unclear how cyprenorphine antagonizes the effects of etorphine, it has been suggested that its greater potency may enable it to displace etorphine in mutual binding sites in the brain[15] . 16-methyl Cyprenorphine, an isoform of Cyprenorphine is an antagonist of the delta, mu and kappa opioid receptors. Its elimination rate constants (Ke) at these receptors are 0.73, 1.77 and 59.6 nM respectively[16] .

Availability[edit]

Etorphine and cyprenorphine come as white powders in a package and cannot be purchased separately.


References[edit]

  1. ^ Calcagnetti, DJ (1990 Jan). "Centrally administered opioid antagonists, nor-binaltorphimine, 16-methyl cyprenorphine and MR2266, suppress intake of a sweet solution". Pharmacology, biochemistry, and behavior. 35 (1): 69–73. PMID 2315372.  Unknown parameter |coauthors= ignored (|author= suggested) (help); Check date values in: |date= (help)
  2. ^ (PDF) http://www.rhinoresourcecenter.com/pdf_files/130/1301707111.pdf.  Missing or empty |title= (help)
  3. ^ (PDF) http://www.rhinoresourcecenter.com/pdf_files/130/1301707111.pdf.  Missing or empty |title= (help)
  4. ^ Dobbs, HE (1968 Apr). "Effect of cyprenorphine (M285), a morphine antagonist, on the distribution and excretion of etorphine (M99), a potent morphine-like drug". The Journal of pharmacology and experimental therapeutics. 160 (2): 407–14. PMID 5647307.  Check date values in: |date= (help)
  5. ^ Bentley KW, Boura ALA, Fitzgerald AE, Hardy DG, McCoubrey A, Aikman ML, Lister RE. Compounds Possessing Morphine-Antagonizing or Powerful Analgesic Effects. Nature, 1965; (206):102-103.
  6. ^ Lowe G, Williams DI. Some Effects of a Hallucinogenic Compound (Cyprenorphine Hydrochloride; M 285) on the Light Reinforced Behaviour of Rats. Nature. 1969; (224):1226.
  7. ^ Wray, SR (1971). "The behavioural effects of levallorphan, cyprenorphine (M285) and amphetamine on repeated Y-maze performance in rats". Psychopharmacologia. 21 (3): 257–67. PMID 5095415.  Unknown parameter |coauthors= ignored (|author= suggested) (help)
  8. ^ (PDF) http://www.jstor.org/stable/pdfplus/3872770.pdf?acceptTC=true.  Missing or empty |title= (help)
  9. ^ Dobbs, HE (1968 Apr). "Effect of cyprenorphine (M285), a morphine antagonist, on the distribution and excretion of etorphine (M99), a potent morphine-like drug". The Journal of pharmacology and experimental therapeutics. 160 (2): 407–14. PMID 5647307.  Check date values in: |date= (help)
  10. ^ (PDF) http://www.jstor.org/stable/pdfplus/3872770.pdf?acceptTC=true.  Missing or empty |title= (help)
  11. ^ (PDF) http://www.rhinoresourcecenter.com/pdf_files/130/1301707111.pdf.  Missing or empty |title= (help)
  12. ^ Wray, SR (1971). "The behavioural effects of levallorphan, cyprenorphine (M285) and amphetamine on repeated Y-maze performance in rats". Psychopharmacologia. 21 (3): 257–67. PMID 5095415.  Unknown parameter |coauthors= ignored (|author= suggested) (help)
  13. ^ Lowe, G (1972). "The effect of LSD-25 on light-reinforced behaviour in the rat". Psychopharmacologia. 27 (3): 255–63. PMID 4642465.  Unknown parameter |coauthors= ignored (|author= suggested) (help)
  14. ^ (PDF) http://www.cpdd.vcu.edu/Media/Index/AwardSpeeches/LewisJ._Eddy1998.pdf.  Missing or empty |title= (help)
  15. ^ Cerletti, C (1974 Nov). "Proceedings: Brain levels of the potent analgesic etorphine in rats and their functional significance". British journal of pharmacology. 52 (3): 440P–441P. PMID 4156490.  Unknown parameter |coauthors= ignored (|author= suggested) (help); Check date values in: |date= (help)
  16. ^ . PMID 3025546.  Missing or empty |title= (help)


Category:Semisynthetic opioids Category:Morphinans Category:Alcohols Category:Ethers Category:Phenols Category:Alkenes Category:Kappa agonists