Cyprenorphine

Cyprenorphine
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • 6,7,8,14-tetrahydro- N-(Cyclopropylmethyl)- 7α-(1-hydroxy-1-methylethyl)- 6,14-endo-ethenonororipavine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H33NO4
Molar mass423.553 g·mol−1
3D model (JSmol)
  • CC(C)(O)[C@H]7C[C@]53/C=C/[C@]7(OC)[C@@H]1Oc6c2c(C[C@H]5N(CC[C@@]123)CC4CC4)ccc6O
  • InChI=1S/C26H33NO4/c1-23(2,29)18-13-24-8-9-26(18,30-3)22-25(24)10-11-27(14-15-4-5-15)19(24)12-16-6-7-17(28)21(31-22)20(16)25/h6-9,15,18-19,22,28-29H,4-5,10-14H2,1-3H3/t18-,19-,22-,24-,25+,26-/m1/s1 checkY
  • Key:VSKIOMHXEUHYSI-KNLIIKEYSA-N checkY
  (verify)

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.[1]

Cyprenorphine is a powerful antagonist of opioid receptors[2] and a highly potent specific antagonist.[3] It blocks the binding of morphine and etorphine to these receptors.[3]

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.[4][5]

Cyprenorphine also has been shown to suppress the intake of sweet solution[2] but doesn't suppress the increase in food consumption that is produced by the alpha-2-adrenoceptor antagonist idazoxan. Idazoxan may lead to the release of endogenous opioid peptides and increase food intake, this effect is attenuated by (-)-naloxone but not by the mu/delta-antagonist cyprenorphine.[6]

  1. ^ Dobbs HE (April 1968). "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): 407–414. PMID 5647307.
  2. ^ a b Calcagnetti DJ, Calcagnetti RL, Fanselow MS (January 1990). "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. doi:10.1016/0091-3057(90)90206-w. PMID 2315372. S2CID 12321010.
  3. ^ a b Keep ME (1971). "Etorphine hydrochloride antagonists used in the capture of the white rhinoceros Ceratotherium simum simum" (PDF). Lammergeyer. 13: 60–68.
  4. ^ Bentley KW, Boura AL, Fitzgerald AE, Hardy DG, Mccoubrey A, Aikman ML, Lister RE (April 1965). "Compounds possessing Morphine-antagonizing or Powerful Analgesic Properties". Nature. 206 (4979): 102–103. Bibcode:1965Natur.206..102B. doi:10.1038/206102a0. PMID 14334338. S2CID 4296776.
  5. ^ Lowe G, Williams DI (December 1969). "Some effects of a hallucinogenic compound (cyprenorphine hydrochloride; M 285) on the light reinforced behaviour of rats". Nature. 224 (5225): 1226. Bibcode:1969Natur.224.1226L. doi:10.1038/2241226a0. PMID 5390897. S2CID 4178326.
  6. ^ Jackson HC, Griffin IJ, Nutt DJ (August 1992). "Endogenous opioids may be involved in idazoxan-induced food intake". Neuropharmacology. 31 (8): 771–776. doi:10.1016/0028-3908(92)90040-V. PMID 1356252. S2CID 19966867.