Methocinnamox

Methocinnamox is an opioid antagonist.

Methocinnamox

Names
IUPAC name (E)-N-[(4R,4aS,7aR,12bR)-3-(Cyclopropylmethyl)-9-hydroxy-7-oxo-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-4a-yl]-3-(4-methylphenyl)prop-2-enamide
Identifiers
CAS Number	117339-76-1 N
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL610884
ChemSpider	24673142
PubChem CID	46877713
InChI InChI=1S/C30H32N2O4/c1-18-2-4-19(5-3-18)8-11-25(35)31-30-13-12-23(34)28-29(30)14-15-32(17-20-6-7-20)24(30)16-21-9-10-22(33)27(36-28)26(21)29/h2-5,8-11,20,24,28,33H,6-7,12-17H2,1H3,(H,31,35)/b11-8+/t24-,28+,29+,30-/m1/s1 Key: PJOHVEQSYPOERL-SHEAVXILSA-N
SMILES CC1=CC=C(C=C1)/C=C/C(=O)N[C@@]23CCC(=O)[C@H]4[C@@]25CCN([C@@H]3CC6=C5C(=C(C=C6)O)O4)CC7CC7
Properties
Chemical formula	C30H32N2O4
Molar mass	484.596 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Mechanism of action

Methocinnamox is an opioid antagonist, it works at the µ-opioid receptor. By being an antagonist, it binds to the receptor but does not activate it, thus blocking the action of agonists such as Fentanyl.

Therapeutic potential

Opioid overdose

In rats, methocinnamox is able to reverse the respiratory depressant effects of fentanyl. However, unlike naloxone, another opioid antagonist, its action lasts around 2 weeks if administered subcutaneously and up to 5 days if administered intravenously. This could make it a better antidote than naloxone in opioid overdoses, because naloxone usually lasts around 30 minutes, there is a need for repeated administration and a danger of renarcotization. By acting longer, methocinnamox prevents these dangers.

Other tests have also shown this result, methocinnamox was able to reverse the respiratory depressant effect of heroin.