Cyprenorphine

Cyprenorphine
	File:Cyprenorphine structure.svg
Clinical data
ATC code	none;
Legal status
Legal status	US: Schedule I;
Identifiers
	IUPAC name 6,7,8,14-tetrahydro- N-(Cyclopropylmethyl)- 7α-(1-hydroxy-1-methylethyl)- 6,14-endo-ethenonororipavine;
CAS Number	4406-22-8 ;
PubChem CID	544534;
ChemSpider	16735758 ;
UNII	1P6HEG5ZHS;
ChEMBL	ChEMBL2106063;
CompTox Dashboard (EPA)	DTXSID80905125 ;
Chemical and physical data
Formula	C26H33NO4
Molar mass	423.553 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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 ; Key:VSKIOMHXEUHYSI-KNLIIKEYSA-N ;
	(verify)

Cyprenorphine (M-285) 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.

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.^[1]^[2]

Cyprenorphine also has been shown to suppress the intake of sweet solution ^[3] but doesn't suppress the increase in food consumption that's 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. ^[4]

References

^ 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): 102–3. Bibcode:1965Natur.206..102B. doi:10.1038/206102a0. PMID 14334338.
^ 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.
^ 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.
^ Jackson HC, Griffin IJ, Nutt DJ (August 1992). "Endogenous opioids may be involved in idazoxan-induced food intake". Neuropharmacology. 31 (8): 771–6. doi:10.1016/0028-3908(92)90040-V. PMID 1356252.

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[pmid14334338-1] 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): 102–3. Bibcode:1965Natur.206..102B. doi:10.1038/206102a0. PMID 14334338.

[pmid5390897-2] 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.

[3] 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.

[4] Jackson HC, Griffin IJ, Nutt DJ (August 1992). "Endogenous opioids may be involved in idazoxan-induced food intake". Neuropharmacology. 31 (8): 771–6. doi:10.1016/0028-3908(92)90040-V. PMID 1356252.

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