Isomethadone

Isomethadone
Clinical data
Other names	WIN-1783, BW 47-442
ATC code	None;
Legal status
Legal status	AU: S9 (Prohibited substance); CA: Schedule I; DE: Anlage II (Authorized trade only, not prescriptible); US: Schedule II; UN: Psychotropic Schedule I;
Identifiers
	IUPAC name (±)-6-(Dimethylamino)-5-methyl-4,4-diphenyl-3-hexanone;
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));
PubChem CID	10072;
ChemSpider	9675;
UNII	12L95QD6KV;
CompTox Dashboard (EPA)	DTXSID40861955 ;
Chemical and physical data
Formula	C21H27NO
Molar mass	309.453 g·mol−1
3D model (JSmol)	Interactive image;
	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; trade nameLiden; 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 g. The salts in use are the hydrobromide (HBr, free base conversion ratio 0.793), hydrochloride (HCl, 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

^ Macdonald F (1997). Dictionary of Pharmacological Agents. CRC Press. p. 1169. ISBN 978-0-412-46630-4. Retrieved 16 May 2012.
^ Morton IK, Hall JM (1999). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer. p. 157. ISBN 978-0-7514-0499-9. Retrieved 16 May 2012.
^ Keats AS, Beecher HK (June 1952). "Analgesic potency and side action liability in man of heptazone, WIN 1161-2, 6-methyl dihydromorphine, Metopon, levo-isomethadone and pentobarbital sodium, as a further effort to refine methods of evaluation of analgesic drugs". The Journal of Pharmacology and Experimental Therapeutics. 105 (2): 109–29. PMID 14928215.
^ Winter CA, Flataker L (November 1952). "Antitussive action of d-isomethadone and d-methadone in dogs". Proceedings of the Society for Experimental Biology and Medicine. 81 (2). New York, N.Y.: Society for Experimental Biology and Medicine: 463–5. doi:10.3181/00379727-81-19912. PMID 13027341. S2CID 36487588.
^ Portoghese PS, Poupaert JH, Larson DL, et al. (June 1982). "Synthesis, X-ray crystallographic determination, and opioid activity of erythro-5-methylmethadone enantiomers. Evidence which suggests that mu and delta opioid receptors possess different stereochemical requirements". Journal of Medicinal Chemistry. 25 (6): 684–8. doi:10.1021/jm00348a015. PMID 6284938.
^ "Final Adjusted Aggregate Production Quotas for Schedule I and II Controlled Substances and Assessment of Annual Needs for the List I Chemicals Ephedrine, Pseudoephedrine, and Phenylpropanolamine for 2014". Code of Federal Regulations.
^ Nordegren T (1 March 2002). The A-Z Encyclopedia of Alcohol and Drug Abuse. Universal-Publishers. p. 366. ISBN 978-1-58112-404-0. Retrieved 16 May 2012.

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[Macdonald1997-1] Macdonald F (1997). Dictionary of Pharmacological Agents. CRC Press. p. 1169. ISBN 978-0-412-46630-4. Retrieved 16 May 2012.

[MortonMorton1999-2] Morton IK, Hall JM (1999). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer. p. 157. ISBN 978-0-7514-0499-9. Retrieved 16 May 2012.

[pmid14928215-3] Keats AS, Beecher HK (June 1952). "Analgesic potency and side action liability in man of heptazone, WIN 1161-2, 6-methyl dihydromorphine, Metopon, levo-isomethadone and pentobarbital sodium, as a further effort to refine methods of evaluation of analgesic drugs". The Journal of Pharmacology and Experimental Therapeutics. 105 (2): 109–29. PMID 14928215.

[pmid13027341-4] Winter CA, Flataker L (November 1952). "Antitussive action of d-isomethadone and d-methadone in dogs". Proceedings of the Society for Experimental Biology and Medicine. 81 (2). New York, N.Y.: Society for Experimental Biology and Medicine: 463–5. doi:10.3181/00379727-81-19912. PMID 13027341. S2CID 36487588.

[pmid6284938-5] Portoghese PS, Poupaert JH, Larson DL, et al. (June 1982). "Synthesis, X-ray crystallographic determination, and opioid activity of erythro-5-methylmethadone enantiomers. Evidence which suggests that mu and delta opioid receptors possess different stereochemical requirements". Journal of Medicinal Chemistry. 25 (6): 684–8. doi:10.1021/jm00348a015. PMID 6284938.

[6] "Final Adjusted Aggregate Production Quotas for Schedule I and II Controlled Substances and Assessment of Annual Needs for the List I Chemicals Ephedrine, Pseudoephedrine, and Phenylpropanolamine for 2014". Code of Federal Regulations.

[Nordegren2002-7] Nordegren T (1 March 2002). The A-Z Encyclopedia of Alcohol and Drug Abuse. Universal-Publishers. p. 366. ISBN 978-1-58112-404-0. Retrieved 16 May 2012.

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See also

References