From Wikipedia, the free encyclopedia
Chemical compound
Phenbenzamine , sold under the brand name Antergan and known by the former developmental code name RP-2339 , is an
antihistamine of the
ethylenediamine class which also has
anticholinergic properties.
[1]
[2] It was introduced in 1941 or 1942 and was the first antihistamine to be introduced for medical use.
[3]
[4]
[5] Soon following its introduction, phenbenzamine was replaced by another antihistamine of the same class known as
mepyramine (pyrilamine; Neoantergan).
[5]
[6] Following this, other antihistamines, such as
diphenhydramine ,
promethazine , and
tripelennamine , were developed and introduced.
[5]
[7] Owing to their
sedative effects, phenbenzamine and promethazine were assessed in the treatment of
manic depression in
France in the 1940s and were regarded as promising therapies for such purposes.
[3] Whereas phenbenzamine was the first clinically useful antihistamine,
piperoxan was the first compound with antihistamine properties to be discovered and was synthesized in the early 1930s.
[7]
Chemistry
Synthesis
Phenbenzamine can be prepared by the reaction of N -benzylaniline with 2-chloroethyldimethylamine.
[8]
[9]
Phenbenzamine synthesis
References
^
"Phenbenzamine" . Encyclopædia Britannica .
^ Maxwell RA, Eckhardt SB (6 December 2012).
"Chloropromazine" . Drug Discovery: A Casebook and Analysis . Springer Science & Business Media. pp. 113–.
ISBN
978-1-4612-0469-5 .
^
a
b Moncrieff, Joanna (2013). "Chlorpromazine: The First Wonder Drug". The Bitterest Pills . Palgrave Macmillan UK. pp. 20–38.
doi :
10.1057/9781137277442_2 .
ISBN
978-1-137-27743-5 .
^ Williams DA, Foye WO, Lemke TL (2002).
"Chapter 29: Estrogen, Progestins, and Androgens" . Foye's Principles of Medicinal Chemistry . Lippincott Williams & Wilkins. pp. 799–.
ISBN
978-0-683-30737-5 .
^
a
b
c Welcome MO (20 June 2018).
Gastrointestinal Physiology: Development, Principles and Mechanisms of Regulation . Springer. pp. 827–.
ISBN
978-3-319-91056-7 .
^ Cundell DR, Mickle KE (11 July 2018).
"Developing the Perfect Antihistamine for use in Allergic Conditions: A Voyage in H1 Selectivity" . In Atta-ur-Rahman (ed.). Frontiers in Clinical Drug Research - Anti-Allergy Agents . Bentham Science Publishers. pp. 29–.
ISBN
978-1-68108-337-7 .
^
a
b Landau R, Achilladelis B, Scriabine A (1999).
Pharmaceutical Innovation: Revolutionizing Human Health . Chemical Heritage Foundation. pp. 230–231.
ISBN
978-0-941901-21-5 .
^
US 2634293 , Kyrides LP, Zienty FB, "Process of preparing a monobasic salt of a secondary amine", issued 7 April 1953, assigned to Monsanto Chemicals
^ Kaye IA, Parris CL, Weiner N (1953). "A Novel N-Alkylation Reaction". Journal of the American Chemical Society . 75 (3): 744–745.
doi :
10.1021/ja01099a508 .
H1
Agonists Antagonists
Others:
Atypical antipsychotics (e.g.,
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ziprasidone ,
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Phenylpiperazine
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trazodone ,
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Tetracyclic antidepressants (e.g.,
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dosulepin (dothiepin) ,
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iprindole ,
lofepramine ,
nortriptyline ,
protriptyline ,
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Typical antipsychotics (e.g.,
chlorpromazine ,
flupenthixol ,
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H2
H3
H4
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Antagonists
3-Quinuclidinyl benzilate
4-DAMP
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Ambutonium bromide
Anisodamine
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AQ-RA 741
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Benactyzine
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Benzydamine
BIBN 99
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CAR-226,086
CAR-301,060
CAR-302,196
CAR-302,282
CAR-302,368
CAR-302,537
CAR-302,668
Caramiphen
Cimetropium bromide
Clidinium bromide
Cloperastine
CS-27349
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Darifenacin
DAU-5884
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Dihexyverine
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EA-3167
EA-3443
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Glycopyrronium bromide (
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Hexahydrodifenidol
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HL-031,120
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+salbutamol )
Isopropamide
J-104,129
Hyoscyamine
Mamba toxin 3
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Mazaticol
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Mepenzolate
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Methylatropine
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Metixene
Muscarinic toxin 7
N-Ethyl-3-piperidyl benzilate
N-Methyl-3-piperidyl benzilate
Nefopam
Octatropine methylbromide (anisotropine methylbromide)
Orphenadrine
Otenzepad (AF-DX 116)
Otilonium bromide
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PBID
PD-102,807
PD-0298029
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pFHHSiD
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Piperidolate
Pirenzepine
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Propantheline bromide
Propiverine
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Revefenacin
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RU-47,213
SCH-57,790
SCH-72,788
SCH-217,443
Scopolamine (hyoscine)
Scopolamine butylbromide (hyoscine butylbromide)
Silahexacyclium
Sofpironium bromide
Solifenacin
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Tetracyclic antidepressants (e.g.,
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Tiemonium iodide
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amitriptylinoxide ,
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nortriptyline ,
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Tridihexethyl
Trihexyphenidyl
Trimebutine
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Tropacine
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Trospium chloride
Typical antipsychotics (e.g.,
chlorpromazine ,
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cyamemazine (cyamepromazine) ,
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Umeclidinium bromide (
+vilanterol )
WIN-2299
Xanomeline
Zamifenacin
Precursors (and
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