Methoclocinnamox

Methoclocinnamox
Clinical data
Other names	MCCAM; MC-CAM; NIH-10420; O-Methylclocinnamox
Identifiers
	IUPAC name (E)-N-[(4R,4aS,7aR,12bR)-3-(cyclopropylmethyl)-9-methoxy-7-oxo-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-4a-yl]-3-(4-chlorophenyl)prop-2-enamide; or; (2E)-3-(4-chlorophenyl)-N-[(5α)-17-(cyclopropylmethyl)-3-methoxy-6-oxo-4,5-epoxymorphinan-14-yl]acrylamide;
PubChem CID	44417373;
ChemSpider	23276873;
ChEMBL	ChEMBL386272;
Chemical and physical data
Formula	C30H31ClN2O4
Molar mass	519.04 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=C2C3=C(C[C@@H]4[C@]5([C@]3(CCN4CC6CC6)[C@@H](O2)C(=O)CC5)NC(=O)/C=C/C7=CC=C(C=C7)Cl)C=C1;
	InChI InChI=1S/C30H31ClN2O4/c1-36-23-10-7-20-16-24-30(32-25(35)11-6-18-4-8-21(31)9-5-18)13-12-22(34)28-29(30,26(20)27(23)37-28)14-15-33(24)17-19-2-3-19/h4-11,19,24,28H,2-3,12-17H2,1H3,(H,32,35)/b11-6+/t24-,28+,29+,30-/m1/s1; Key:LZSMGMMAKBCSRL-WDJVXPEUSA-N;

Methoclocinnamox (MCCAM; developmental code name NIH-10420) is a selective pseudo-irreversible partial agonist of the μ-opioid receptor (MOR). It shows a mixture of opioid agonist- and antagonist-like effects. The drug has long-lasting effects and is insurmountable by other MOR ligands.

MCCAM was derived from clocinnamox (CCAM), was first described by 1995, and was of interest in the potential treatment of opioid dependence. However, it was not further developed and was never marketed. A close analogue of MCCAM, methocinnamox (MCAM), which in contrast to MCCAM acts as a MOR pseudo-irreversible antagonist, was first described in 2000 and is under development for the treatment of opioid use disorder and opioid overdose as of 2023.