Cyprodime

Cyprodime is an opioid antagonist from the morphinan family of drugs.

Cyprodime
Clinical data
Other namesCyprodime
ATC code
  • none
Identifiers
IUPAC name
  • (–)-N-(Cyclopropylmethyl)-4,14-dimethoxymorphinan-6-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H29NO3
Molar mass355.478 g·mol−1
3D model (JSmol)
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 N
  • Key:INUCRGMCKDQKNA-ILWGZMRPSA-N N
 NY (what is this?)  (verify)

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]

See also
  • Tianeptine, an atypical, selective MOR full-agonist licensed for major depression since 1989.
  • Samidorphan, an opioid antagonist preferring the MOR, which is under development for major depression.

References
  1. Schmidhammer H, Burkard WP, Eggstein-Aeppli L, Smith CF (February 1989). "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. 32 (2): 418–21. doi:10.1021/jm00122a021. PMID 2536439.
  2. Márki A, Monory K, Otvös F, Tóth G, Krassnig R, Schmidhammer H, et al. (October 1999). "Mu-opioid receptor specific antagonist cyprodime: characterization by in vitro radioligand and [35S]GTPgammaS binding assays". European Journal of Pharmacology. 383 (2): 209–14. doi:10.1016/s0014-2999(99)00610-x. PMID 10585536.
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