DPH-362 explained

Width:

250px

Cas Number:

28916-83-8

Pubchem:

13465

Chemspiderid:

12888

Synonyms:

PD129167

Iupac Name:

N,N-dimethyl-4,4-diphenylbut-3-en-1-amine| C=18 | H=21 | N=1| molecular_weight = | SMILES = CN(C)CCC=C(C1=CC=CC=C1)C2=CC=CC=C2| Jmol = | StdInChI = 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| StdInChI_comment = | StdInChIKey = ZRPJJBLGKLVADE-UHFFFAOYSA-N| density = | density_notes = | melting_point = | melting_high = | melting_notes = | boiling_point = | boiling_notes = | solubility = | sol_units = | specific_rotation = }}

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]

See also

• Amitriptyline
• γ-Butyrolactone

References

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Notes and References

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