Cyprodime

Cyprodime
Clinical data
Other names	Cyprodime
ATC code	none;
Identifiers
	IUPAC name (–)-N-(Cyclopropylmethyl)-4,14-dimethoxymorphinan-6-one;
CAS Number	118111-54-9 ;
PubChem CID	5748293;
ChemSpider	4677866 ;
ChEMBL	ChEMBL322796 ;
CompTox Dashboard (EPA)	DTXSID90922601 ;
Chemical and physical data
Formula	C22H29NO3
Molar mass	355.471 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C4CC[C@@]3(OC)[C@@H]2N(CC[C@]3(c1c(cccc1OC)C2)C4)CC5CC5;
	InChI InChI=1S/C22H29NO3/c1-25-18-5-3-4-16-12-19-22(26-2)9-8-17(24)13-21(22,20(16)18)10-11-23(19)14-15-6-7-15/h3-5,15,19H,6-14H2,1-2H3/t19-,21-,22+/m0/s1 ; Key:INUCRGMCKDQKNA-ILWGZMRPSA-N ;
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Cyprodime is an opioid antagonist from the morphinan family of drugs.

Cyprodime is a selective opioid antagonist which blocks the μ-opioid receptor,^[1] but without affecting the δ-opioid or κ-opioid receptors. This makes it useful for scientific research as it allows the μ-opioid receptor to be selectively deactivated so that the actions of the δ and κ receptors can be studied separately, in contrast to better known opioid antagonists such as naloxone which block all three opioid receptor subtypes.^[2]

References

^ Schmidhammer H, Burkard WP, Eggstein-Aeppli L, Smith CF. Synthesis and biological evaluation of 14-alkoxymorphinans. 2. (−)-N- (cyclopropylmethyl)- 4,14-dimethoxymorphinan- 6-one, a selective mu opioid receptor antagonist. Journal of Medicinal Chemistry. 1989 Feb;32(2):418-21. PMID 2536439
^ Márki A, Monory K, Otvös F, Tóth G, Krassnig R, Schmidhammer H, Traynor JR, Roques BP, Maldonado R, Borsodi A. Mu-opioid receptor specific antagonist cyprodime: characterization by in vitro radioligand and [35S]GTPgammaS binding assays. European Journal of Pharmacology. 1999 Oct 27;383(2):209-14. PMID 10585536

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[1] Schmidhammer H, Burkard WP, Eggstein-Aeppli L, Smith CF. Synthesis and biological evaluation of 14-alkoxymorphinans. 2. (−)-N- (cyclopropylmethyl)- 4,14-dimethoxymorphinan- 6-one, a selective mu opioid receptor antagonist. Journal of Medicinal Chemistry. 1989 Feb;32(2):418-21. PMID 2536439

[2] Márki A, Monory K, Otvös F, Tóth G, Krassnig R, Schmidhammer H, Traynor JR, Roques BP, Maldonado R, Borsodi A. Mu-opioid receptor specific antagonist cyprodime: characterization by in vitro radioligand and [35S]GTPgammaS binding assays. European Journal of Pharmacology. 1999 Oct 27;383(2):209-14. PMID 10585536

[1]

[2]

See also

References