DPH-362

DPH-362
Clinical data
Other names	PD129167
Identifiers
	IUPAC name N,N-dimethyl-4,4-diphenylbut-3-en-1-amine;
CAS Number	28916-83-8;
PubChem CID	13465;
ChemSpider	12888;
Chemical and physical data
Formula	C18H21N
Molar mass	251.373 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN(C)CCC=C(C1=CC=CC=C1)C2=CC=CC=C2;
	InChI InChI=InChI=1S/C18H21N/c1-19(2)15-9-14-18(16-10-5-3-6-11-16)17-12-7-4-8-13-17/h3-8,10-14H,9,15H2,1-2H3; Key:ZRPJJBLGKLVADE-UHFFFAOYSA-N;

DPH-362 is a simplified amitriptyline analog created by omission of the two-carbon dibenzosuberane bridge (the seven membered ring). The resulting compound still had activity in a test to explore TCA sodium channel blockers with analgesic properties.^[1]^[2]

It is based on previous structures such as Spasmolytic A29 (one of the active ingredients in Ketogan)^[3]^[4] and SKF-89976A.

Synthesis

γ-Butyrolactone is used in the synthesis of DPH-362.^[5]

DPH-362 synthesis

^ Bölcskei H, Tarnawa I, Kocsis P (June 2008). "Voltage-gated sodium channel blockers, 2001-2006: An overview". Medicinal Chemistry Research. 17 (2–7): 356–368. doi:10.1007/s00044-007-9071-2.
^ Hudgens DP, Taylor C, Batts TW, Patel MK, Brown ML (December 2006). "Discovery of diphenyl amine based sodium channel blockers, effective against hNav1.2". Bioorganic & Medicinal Chemistry. 14 (24): 8366–8378. doi:10.1016/j.bmc.2006.09.010. PMC 2756728. PMID 17035036.
^ Petersen PV (1951). "Studies on a new spasmolytic compound 1,1-diphenyl-3-dimethylaminobutene-1 (A29), related to methadone, and on the combined use of this compound and a potent analgesic, ketobemidone (A21)". Acta Pharmacologica et Toxicologica. 7 (1): 51–64. doi:10.1111/j.1600-0773.1951.tb02849.x. PMID 14829296.
^ Ebert B, Thorkildsen C, Andersen S, Christrup LL, Hjeds H (September 1998). "Opioid analgesics as noncompetitive N-methyl-D-aspartate (NMDA) antagonists". Biochemical Pharmacology. 56 (5): 553–559. doi:10.1016/s0006-2952(98)00088-4. PMID 9783723.
^ WO 2006023757, Brown ML, "Novel tricyclic, bicyclic, monocyclic, and acyclic amines as potent sodium channel blocking agents", published 2 March 2006, assigned to University of Virginia

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