Dimethylaminopivalophenone

Opioid analgesic drug

Dimethylaminopivalophenone
Identifiers

IUPAC name 3-(dimethylamino)-2,2-dimethyl-1-phenylpropan-1-one
CAS Number	15451-29-3^Y
PubChem CID	84922
ChemSpider	76610
UNII	83LLR55ETP
CompTox Dashboard (EPA)	DTXSID90165652
Chemical and physical data
Formula	C₁₃H₁₉NO
Molar mass	205.301 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CN(CC(C(=O)C1=CC=CC=C1)(C)C)C
InChI InChI=1S/C13H19NO/c1-13(2,10-14(3)4)12(15)11-8-6-5-7-9-11/h5-9H,10H2,1-4H3 Key:WKJYCZMXCFRIEO-UHFFFAOYSA-N

Dimethylaminopivalophenone^[1]^[2] is an opioid analgesic with a potency ½ that of morphine.^{[citation needed]} It was initially discovered by Russian scientists in 1954 and subsequently rediscovered in the US in 1969.^[3] Its LD₅₀ in mice is 83 mg/kg.^[4] It has never been marketed commercially.^{[citation needed]}

References

^ Brewster JH, Eliel EL (2011). "Carbon-Carbon Alkylations with Amines and Ammonium Salts". Organic Reactions. 7 (3): 99–197. doi:10.1002/0471264180.or007.03. ISBN 9780471264187.
^ Kleinman EF (April 2011). "Dimethyl(methylene)ammonium Iodide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rd346. ISBN 978-0471936237. {{cite book}}: |journal= ignored (help)
^ Atwal MS, Bauer L, Dixit SN, Gearien JE, Megahy M, Morris R, Pokorny C (November 1969). "Analgetics. II. Relationship between structure and activity of some beta-amino ketones". Journal of Medicinal Chemistry. 12 (6): 994–7. doi:10.1021/jm00306a006. PMID 5351480.
^ "2,2-dimethyl-3-(dimethylamino)-Propiophenone". ChemIDplus. Retrieved 2 October 2015.

Analgesics (N02A, N02B)

Opioids

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

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^§
Potassium openers	Flupirtine^‡