Isomethadone

Isomethadone
Systematic (IUPAC) name
	(±)-6-(dimethylamino)-5-methyl-4,4-diphenyl-3-hexanone
Clinical data
Legal status	AU: S9 (Prohibited); CA: Schedule I; DE: Anlage II (Prohibited); US: Schedule II; Schedule I (UN);
Identifiers
CAS Number	466-40-0; 5341-49-1 (HCl); 26594-41-2 ((R)-form); 561-10-4 ((S)-form); 7484-81-2 ((S)-form (HCl))
ATC code	None
PubChem	CID: 10072
ChemSpider	9675
UNII	12L95QD6KV
Synonyms	WIN-1783, BW 47-442
Chemical data
Formula	C21H27NO
Molecular mass	309.445 g/mol
	SMILES O=C(CC)C(C1=CC=CC=C1)(C(C)CN(C)C)C2=CC=CC=C2 ;
	InChI InChI=1S/C21H27NO/c1-5-20(23)21(17(2)16-22(3)4,18-12-8-6-9-13-18)19-14-10-7-11-15-19/h6-15,17H,5,16H2,1-4H3 ; Key:IFKPLJWIEQBPGG-UHFFFAOYSA-N ;

Isomethadone (INN, BAN; Liden), also known as isoamidone, is a synthetic opioid analgesic and antitussive related to methadone that was used formerly as a pharmaceutical drug but is now no longer marketed.^[1]^[2]^[3]^[4] Isomethadone was used as both an analgesic and antitussive. It binds to and activates both the μ- and δ-opioid receptors, with the (S)-isomer being the more potent of its two enantiomers.^[5] Isomethadone is a Schedule II controlled substance in the United States, with an ACSCN of 9226 and a 2014 aggregate manufacturing quota of 5 grammes. The salts in use are the hydrobromide (free base conversion ratio 0.793), hydrochloride (0.894), and HCl monohydrate (0.850).^[6] Isomethadone is also regulated internationally as a Schedule I controlled substance under the United Nations Single Convention on Narcotic Drugs of 1961.^[7]

References

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