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MedKoo Cat#: 208422 | Name: Methocinnamox

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Methocinnamox, also known as RX 849030, is a mu opioid receptor antagonist with a long duration of action. Methocinnamox antagonizes the behavioral suppressant effects of morphine without impairing delayed matching-to-sample accuracy in rhesus monkeys. MCAM could potentially be used as both a rescue and long-term treatment for opioid misuse.

Chemical Structure

Methocinnamox
Methocinnamox
CAS#117339-76-1

Theoretical Analysis

MedKoo Cat#: 208422

Name: Methocinnamox

CAS#: 117339-76-1

Chemical Formula: C30H32N2O4

Exact Mass: 484.2362

Molecular Weight: 484.60

Elemental Analysis: C, 74.36; H, 6.66; N, 5.78; O, 13.21

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
MCAM; Methocinnamox; RX 849030; RX849030; RX-849030;
IUPAC/Chemical 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
InChi Key
PJOHVEQSYPOERL-SHEAVXILSA-N
InChi Code
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
SMILES Code
CC1=CC=C(/C=C/C(N[C@]23[C@]4(CCN(CC5CC5)[C@@H]3CC6=C4C7=C(O)C=C6)[C@@H](O7)C(CC2)=O)=O)C=C1
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 484.60 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Jimenez VM Jr, Castaneda G, France CP. Methocinnamox Reverses and Prevents Fentanyl-Induced Ventilatory Depression in Rats. J Pharmacol Exp Ther. 2021 Apr;377(1):29-38. doi: 10.1124/jpet.120.000387. Epub 2021 Jan 11. PMID: 33431611; PMCID: PMC7985616. 2: Townsend EA. The lasting impact of methocinnamox on opioid self- administration. Neuropsychopharmacology. 2020 Nov;45(12):1963-1964. doi: 10.1038/s41386-020-0717-9. Epub 2020 May 22. PMID: 32444781; PMCID: PMC7547696. 3: Minervini V, Disney A, Husbands SM, France CP. Methocinnamox (MCAM) antagonizes the behavioral suppressant effects of morphine without impairing delayed matching-to-sample accuracy in rhesus monkeys. Psychopharmacology (Berl). 2020 Oct;237(10):3057-3065. doi: 10.1007/s00213-020-05592-y. Epub 2020 Aug 9. PMID: 32772146; PMCID: PMC8114947. 4: Gerak LR, Minervini V, Latham E, Ghodrati S, Lillis KV, Wooden J, Disney A, Husbands SM, France CP. Methocinnamox Produces Long-Lasting Antagonism of the Behavioral Effects of µ-Opioid Receptor Agonists but Not Prolonged Precipitated Withdrawal in Rats. J Pharmacol Exp Ther. 2019 Nov;371(2):507-516. doi: 10.1124/jpet.119.260331. Epub 2019 Aug 22. PMID: 31439807; PMCID: PMC6863459. 5: Maguire DR, Gerak LR, Woods JH, Husbands SM, Disney A, France CP. Long- Lasting Effects of Methocinnamox on Opioid Self-Administration in Rhesus Monkeys. J Pharmacol Exp Ther. 2019 Jan;368(1):88-99. doi: 10.1124/jpet.118.252353. Epub 2018 Nov 6. PMID: 30401680. 6: Jordan CG, Kennalley AL, Roberts AL, Nemes KM, Dolma T, Piper BJ. The Potential of Methocinnamox as a Future Treatment for Opioid Use Disorder: A Narrative Review. Pharmacy (Basel). 2022 Apr 19;10(3):48. doi: 10.3390/pharmacy10030048. PMID: 35645327; PMCID: PMC9149874. 7: Zamora JC, Smith HR, Jennings EM, Chavera TS, Kotipalli V, Jay A, Husbands SM, Disney A, Berg KA, Clarke WP. Long-term antagonism and allosteric regulation of mu opioid receptors by the novel ligand, methocinnamox. Pharmacol Res Perspect. 2021 Dec;9(6):e00887. doi: 10.1002/prp2.887. PMID: 34713624; PMCID: PMC8554411. 8: Maguire DR, Gerak LR, Sanchez JJ, Javors MA, Disney A, Husbands SM, France CP. Effects of acute and repeated treatment with methocinnamox, a mu opioid receptor antagonist, on fentanyl self-administration in rhesus monkeys. Neuropsychopharmacology. 2020 Nov;45(12):1986-1993. doi: 10.1038/s41386-020-0698-8. Epub 2020 May 6. PMID: 32375158; PMCID: PMC7547678. 9: Gerak LR, Maguire DR, Woods JH, Husbands SM, Disney A, France CP. Reversal and Prevention of the Respiratory-Depressant Effects of Heroin by the Novel μ-Opioid Receptor Antagonist Methocinnamox in Rhesus Monkeys. J Pharmacol Exp Ther. 2019 Feb;368(2):229-236. doi: 10.1124/jpet.118.253286. Epub 2018 Nov 21. PMID: 30463875; PMCID: PMC6337004. 10: Broadbear JH, Sumpter TL, Burke TF, Husbands SM, Lewis JW, Woods JH, Traynor JR. Methocinnamox is a potent, long-lasting, and selective antagonist of morphine-mediated antinociception in the mouse: comparison with clocinnamox, beta-funaltrexamine, and beta-chlornaltrexamine. J Pharmacol Exp Ther. 2000 Sep;294(3):933-40. PMID: 10945843.