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Tonazocine

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Chemical compound

Pharmaceutical compound

Tonazocine
Clinical data


ATC code	None
Legal status
Legal status	In general: non-regulated
Identifiers
IUPAC name 1-[(2S,6R,11S)-8-hydroxy-3,6,11-trimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocin-11-yl]octan-3-one
CAS Number	71461-18-2
PubChemCID	72177
ChemSpider	65150
UNII	J356A16LLK
Chemical and physical data
Formula	C₂₃H₃₅NO₂
Molar mass	357.538 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(CCCCC)CC[C@@]3([C@H]2N(CC[C@@]3(c1c(ccc(O)c1)C2)C)C)C
InChI InChI=1S/C23H35NO2/c1-5-6-7-8-18(25)11-12-23(3)21-15-17-9-10-19(26)16-20(17)22(23,2)13-14-24(21)4/h9-10,16,21,26H,5-8,11-15H2,1-4H3/t21-,22+,23+/m0/s1 Key:UDNUCVYCLQJJBY-YTFSRNRJSA-N

Tonazocine (WIN-42,156) is anopioid analgesic of thebenzomorphan family which made it tophase II clinical trials for the treatment of postoperative pain,^[1] but development was apparently ceased and ultimately it was never marketed. Tonazocine is apartial agonist at both themu-opioid anddelta-opioid receptors, but acting more like anantagonist at the former and more like anagonist at the latter.^[2]^[3] It lacks most of theside effects of other opioids such asadverse effects on thecardiovascular system andrespiratory depression, but it can causesedation (although to a lesser degree of typical opioids), and in some patients it may inducehallucinations (probably via binding to and activating theκ-opioid receptor).^[4]

References

[edit]

^American Chemical Society. Division of Medicinal Chemistry (1990).Annual Reports in Medicinal Chemistry. Academic Press. p. 12.ISBN 978-0-12-040525-1. Retrieved30 November 2011.
^Ward SJ, Pierson AK, Michne WF (February 1985). "Pharmacological profiles of tonazocine (Win 42156) and zenazocine (Win 42964)".Neuropeptides.5 (4–6):375–8.doi:10.1016/0143-4179(85)90032-0.PMID 2860595.S2CID 20674308.
^Hudzik TJ, Howell A, Payza K, Cross AJ (May 2000). "Antiparkinson potential of delta-opioid receptor agonists".European Journal of Pharmacology.396 (2–3):101–7.doi:10.1016/S0014-2999(00)00209-0.PMID 10822062.
^Aronson, Jeffrey K. (30 November 2009).Meyler's Side Effects of Analgesics and Anti-inflammatory Drugs. Elsevier. p. 154.ISBN 978-0-444-53273-2. Retrieved30 November 2011.

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 Tegileridine 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

v t e Hallucinogens
Psychedelics (5-HT_2A agonists)	Tryptamines (e.g.,DMT,psilocin,psilocybin,bufotenin,5-MeO-DMT,AMT) Phenethylamines (e.g.,mescaline,2C-B,DOM,MDA,TMA,2C-B-FLY,25I-NBOMe) Lysergamides (e.g.,LSD,ergine,isoergine) Others (e.g.,efavirenz,IHCH-7113,MK-212,quipazine,RH-34) For a full list of serotonergic psychedelics, see the navboxhere and the listhere instead.
Dissociatives (NMDA antagonists)	Arylcyclohexylamines (e.g.,ketamine (K),phencyclidine (PCP),methoxetamine (MXE),tiletamine) Adamantanes (e.g.,memantine,amantadine) Diarylethylamines (e.g.,diphenidine,ephenidine,methoxphenidine) Morphinans (e.g.,dextromethorphan (DXM),dextrorphan (DXO)) Inhalants (e.g.,nitrous oxide (N₂O),xenon (Xe)) Others (e.g.,alkyl nitrites/poppers,aptiganel,dexoxadrol,dizocilpine (MK-801),etoxadrol,selfotel) For a full list of dissociatives, see the navboxhere instead.
Deliriants (mACh antagonists)	Tropanes:Atropine Hyoscyamine Scopolamine (hyoscine) Antihistamines:Brompheniramine Chloropyramine Chlorphenamine (chlorpheniramine) Clemastine Cyclizine Cyproheptadine Dimenhydrinate Diphenhydramine Doxylamine Meclizine Mepyramine Pheniramine Phenyltoloxamine Promethazine Tripelennamine Triprolidine Others:Benactyzine Benapryzine (benaprizine) Benzatropine (benztropine) Biperiden BZ (QNB) CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,668 CS-27349 Cycrimine Dicycloverine Ditran (JB-329) EA-3167 EA-3443 EA-3580 EA-3834 Flavoxate JB-318 JB-336 Orphenadrine Oxybutynin Procyclidine Tolterodine Trihexyphenidyl Tropicamide Tropine benzilate WIN-2299
KOR agonists	Salvinoids (terpenoids):2-EMSB 2-MMSB RB-64 (22-thiocyanatosalvinorin A) Salvinorin A Benzomorphans:Alazocine Bremazocine Cyclazocine Ketazocine Metazocine MR-2034 Pentazocine Phenazocine Morphinans:Butorphanol Cyclorphan Cyprenorphine Diprenorphine Heroin Levallorphan Levomethorphan Levorphanol Morphine Nalbuphine Nalmefene Nalorphine Oxilorphan Proxorphan Racemethorphan Racemorphan Xorphanol Arylacetamides:Enadoline LPK-26 Niravoline Spiradoline U-50488 U-69593 Others:HZ-2 Tifluadom
GABA_A agonists	Isoxazoles:Gaboxadol (THIP) Ibotenic acid (Amanita muscaria) Muscimol (Amanita muscaria) Indirect GABA_A receptor agonists:GABA_A receptor positive allosteric modulators (nonbenzodiazepines/Z-drugs) (e.g.,eszopiclone,zaleplon,zolpidem,zopiclone) GABA reuptake inhibitors (e.g.,CI-966)
Oneirogens (unknown mech.)	Harmala alkaloids/β-carbolines (e.g.,harmine,harmaline,tetrahydroharmine,6-methoxyharmalan,6-MeO-THH) (found inPeganum harmala,Banisteriopsis caapi) Iboga alkaloids/azepinoindoles (e.g.,ibogaine,noribogaine) (found inTabernanthe iboga)
Cannabinoids (CB₁ agonists)	Phytocannabinoids (e.g.,Δ⁹-THC (dronabinol),CBN,Δ⁸-THC) Synthetic cannabinoids (e.g.,nabilone,JWH-018,JWH-073,HU-210) For a full list of cannabinoids, see the navboxhere and the listhere instead.
Others	Aminochromes (e.g.,adrenochrome,adrenolutin) Carbogen Glaucine Hallucinogenic bolete mushrooms (e.g.,Lanmaoa asiatica) Jenkem Kykeon (Eleusinian Mysteries) Nutmeg (e.g.,myristicin,elemicin) Soma (haoma)
See also:Psychedelics Dissociatives Entactogens Stimulants Depressants List of hallucinogens