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Alimadol

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Chemical compound Not to be confused with adimolol. Pharmaceutical compound

Alimadol
Clinical data

ATC code	None
Identifiers
IUPAC name N-(3-methoxy-3,3-diphenylpropyl)-2-propen-1-amine
CAS Number	52742-40-2
PubChem CID	176882
ChemSpider	154055
UNII	8ET970D66K
ChEMBL	ChEMBL2106661
CompTox Dashboard (EPA)	DTXSID20200727
Chemical and physical data
Formula	C₁₉H₂₃NO
Molar mass	281.399 g·mol
3D model (JSmol)	Interactive image
SMILES O(C)C(c1ccccc1)(c2ccccc2)CCNC\C=C
InChI InChI=1S/C19H23NO/c1-3-15-20-16-14-19(21-2,17-10-6-4-7-11-17)18-12-8-5-9-13-18/h3-13,20H,1,14-16H2,2H3 Key:QFSWEWNANAHUNE-UHFFFAOYSA-N

Alimadol (INN; A-4020) is an opioid analgesic related to methadone which was never marketed.

Synthesis

Patent: Precursor (benzyl group sidechain):

benzhydryl methyl ether (1)
β-chloroethylamine (2)
1,1-Diphenyl-1-methoxy-3-aminopropane: PC21534188 (3)
Allyl bromide (4)

See also

Methadone

References

Ganellin CR, Triggle DJ (1997). Dictionary of Pharmacological Agents. CRC Press. p. 47. ISBN 978-0-412-46630-4. Retrieved 11 May 2012.
US 3960960, Hollinger R, Wendtlandt W, Schneider G, "1,1-Diphenyl-1-lower alkoxy-amino-alkanes and the salts thereof", issued 1 June 1976, assigned to Chemie Linz AG
Hoellinger Roderich Dr, CH478088A (1969 to Chemie Linz Ag).

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Analgesics (N02A, N02B)

Opiates/opium	Codeine +aspirin +paracetamol Morphine (+naltrexone) Opium Laudanum Paregoric
Semisynthetic	Acetyldihydrocodeine Benzylmorphine Buprenorphine (+naloxone) Butorphanol Desomorphine Diamorphine (heroin) 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

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

Ion channel
modulators

Calcium blockers

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

Potassium openers

Flupirtine

Others

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

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Opioid receptor modulators

μ-opioid
(MOR)

Agonists
(abridged;
full list)

Antagonists

δ-opioid
(DOR)

Agonists

Antagonists

κ-opioid
(KOR)

Agonists

Antagonists

Nociceptin
(NOP)

Agonists

Antagonists

Others

Propeptides: β-Lipotropin (proendorphin)
Prodynorphin
Proenkephalin
Pronociceptin
Proopiomelanocortin (POMC)

Others: Kyotorphin (met-enkephalin releaser/degradation stabilizer)

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