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Isomethadone

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From Wikipedia, the free encyclopedia

Opioid analgesic and cough suppressant drug

Pharmaceutical compound

Isomethadone
Clinical data

Other names	WIN-1783, BW 47-442
ATC code	None
Legal status
Legal status	AU: S9 (Prohibited substance) BR: Class A1 (Narcotic drugs)^[1] 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) 7487-81-2 ((S)-form (HCl))
PubChemCID	10072
ChemSpider	9675
UNII	12L95QD6KV
KEGG	D12676^Y
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 asisoamidone) is asynthetic opioid analgesic andantitussive related tomethadone that was used formerly as apharmaceutical drug but is now no longer marketed.^[2]^[3]^[4]^[5] Isomethadone was used as both ananalgesic andantitussive. It binds to and activates both theμ- andδ-opioid receptors, with the (S)-isomer being the morepotent of the twoenantiomers.^[6] Isomethadone is aSchedule II controlled substance in theUnited States, with an ACSCN of 9226 and a 2014 aggregate manufacturing quota of 5 g. Thesalts in use are the hydrobromide (HBr, free base conversion ratio 0.793), hydrochloride (HCl, 0.894), and HCl monohydrate (0.850).^[7] Isomethadone is also regulated internationally as aSchedule I controlled substance under theUnited Nations Single Convention on Narcotic Drugs of 1961.^[8]

References

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^Anvisa (2023-03-31)."RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União (published 2023-04-04).Archived from the original on 2023-08-03. Retrieved2023-08-16.
^Macdonald F (1997).Dictionary of Pharmacological Agents. CRC Press. p. 1169.ISBN 978-0-412-46630-4. Retrieved16 May 2012.
^Morton IK, Hall JM (1999).Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer. p. 157.ISBN 978-0-7514-0499-9. Retrieved16 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.doi:10.1016/S0022-3565(25)05014-1.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. Archived fromthe original on 2016-03-04. Retrieved2016-02-28.
^Nordegren T (1 March 2002).The A-Z Encyclopedia of Alcohol and Drug Abuse. Universal-Publishers. p. 366.ISBN 978-1-58112-404-0. Retrieved16 May 2012.

Analgesics (N02A,N02B)

Opioids

Opiates/opium	Codeine^# +aspirin +paracetamol Morphine^# (+naltrexone) Opium Laudanum Paregoric
Semisynthetic	Acetyldihydrocodeine Benzylmorphine Buprenorphine (+naloxone) Butorphanol Desomorphine Dihydrocodeine (+paracetamol) Dihydromorphine Etorphine Ethylmorphine Hydrocodone (+paracetamol,+ibuprofen,+aspirin) Hydromorphinol Hydromorphone Levorphanol Metopon Nalbuphine Nicocodeine Nicodicodine Nicomorphine Oxycodone (+paracetamol,+aspirin,+ibuprofen,+naloxone,+naltrexone) Oxymorphone Papaveretum Thebacon
Synthetic	Alfentanil Alphaprodine Anileridine Bezitramide Carfentanil Dextromoramide Dextropropoxyphene Dezocine Dimenoxadol Dipipanone Ethoheptazine Fentanyl^# (+fluanisone) Ketobemidone Lofentanil Meptazinol Methadone^# NFEPP Norpipanone Oliceridine Pentazocine Pethidine (meperidine) Phenadoxone Phenazocine Phenoperidine Piminodine Piritramide Proheptazine Propiram Remifentanil Sufentanil Tapentadol Tilidine Tramadol (+celecoxib,+paracetamol) Viminol

Paracetamol-type

NSAIDs

Propionates	Benoxaprofen^‡ Fenoprofen Flurbiprofen Ibuprofen^# (Dexibuprofen) (+paracetamol) Ketoprofen (Dexketoprofen) Loxoprofen Naproxen Oxaprozin Suprofen Tiaprofenic acid Zaltoprofen
Oxicams	Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam
Acetates	Acemetacin Bromfenac Diclofenac Etodolac Indometacin (Indometacin farnesil) Ketorolac Sulindac Tolmetin Zomepirac^‡
COX-2 inhibitors	Celecoxib (+tramadol) Etoricoxib Lumiracoxib^‡ Parecoxib Rofecoxib^‡ Valdecoxib^‡
Fenamates	Flufenamic acid Meclofenamic acid Mefenamic acid Tolfenamic acid
Salicylates	Aspirin (acetylsalicylic acid)^# (+paracetamol/caffeine) Aloxiprin Benorylate Carbasalate calcium Choline salicylate Diflunisal Dipyrocetyl Ethenzamide Guacetisal Imidazole salicylate Magnesium salicylate Morpholine salicylate Potassium salicylate Salicin Salicylamide Salsalate Sodium salicylate Wintergreen (methyl salicylate)
Pyrazolones	Aminophenazone^‡ Ampyrone Metamizole (dipyrone) Nifenazone Phenazone Propyphenazone (+paracetamol/caffeine)
Others	Benzydamine Floctafenine Glafenine Nabumetone Nimesulide Proquazone

Cannabinoids

Ion channel
modulators

Calcium blockers	Alcohol (ethanol) Gabapentin Gabapentin enacarbil Leconotide Mirogabalin Pregabalin Ziconotide
Sodium blockers	Carbamazepine Lacosamide Local anesthetics (e.g.,cocaine,lidocaine) Mexiletine Nefopam Tricyclic antidepressants (e.g.,amitriptyline^#) Na_v1.7/1.8-selective:DSP-2230^§ Funapide^§ PF-05089771^§ Suzetrigine
Potassium openers	Flupirtine^‡

Myorelaxants

Others

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Cough and cold preparations (R05)

Expectorants

Mucolytics

Cough suppressants

Opium alkaloids, opioids, and derivatives	Acetyldihydrocodeine Benzylmorphine Butorphanol Codeine^# (+guaifenesin) Dextromethorphan Dihydrocodeine Dimemorfan Ethylmorphine Heroin Hydrocodone (+guaifenesin,+homatropine) Hydromorphone Laudanum Levomethadone Levopropoxyphene Methadone Nicocodeine Nicodicodeine Normethadone Noscapine Pholcodine Thebacon
Other	Alloclamide Benproperine Benzonatate Bibenzonium bromide Butamirate Clobutinol Clofedanol Cloperastine Dibunate Dimethoxanate Diphenhydramine Dropropizine Droxypropine Fedrilate Fominoben Gefapixant Glaucine Isoaminile Levodropropizine Meprotixol Moguisteine Morclofone Nepinalone Oxeladin Oxolamine Pentoxyverine Pipazetate Piperidione Prenoxdiazine Tipepidine Zipeprol