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Typical antipsychotic
Butaperazine (Repoise , Tyrylen ) is a
typical antipsychotic of the
phenothiazine class.
[2] It was approved in 1967, and possibly discontinued in the 1980s.
Synthesis
Patent:
[3]
2-Butyrylphenothiazine [25244-91-1] (1 ) is the requisite starting material for carrying out the procedure. It is prepared in a manner that is synonymous with the method used in the
propiomazine and
propiopromazine already discussed.
The 1-(γ-chloropropyl)-4-methylpiperazine [104-16-5] (2 ) is prepared in the conventional way from alkylating
1-methylpiperazine and
1-Bromo-3-chloropropane .
Sodamide is used to extract the 10-H thereby facilitating the nucleophilic substitution reaction. And completing the instalment of the sidechain.
See also
References
α1
Agonists Antagonists
Abanoquil
Ajmalicine
Alfuzosin
Anisodamine
Anisodine
Atiprosin
Atypical antipsychotics (e.g.,
brexpiprazole ,
clozapine ,
olanzapine ,
quetiapine ,
risperidone )
Benoxathian
Beta blockers (e.g.,
adimolol ,
amosulalol ,
arotinolol ,
carvedilol ,
eugenodilol ,
labetalol )
Buflomedil
Bunazosin
Corynanthine
Dapiprazole
Domesticine
Doxazosin
Ergolines (e.g.,
acetergamine ,
ergotamine ,
dihydroergotamine ,
lisuride ,
nicergoline ,
terguride )
Etoperidone
Fenspiride
Hydroxyzine
Indoramin
Ketanserin
L-765,314
mCPP
Mepiprazole
Metazosin
Monatepil
Moxisylyte
Naftopidil
Nantenine
Neldazosin
Niaprazine
Niguldipine
Pardoprunox
Pelanserin
Perlapine
Phendioxan
Phenoxybenzamine
Phentolamine
Phenylpiperazine
antidepressants (e.g.,
hydroxynefazodone ,
nefazodone ,
trazodone ,
triazoledione )
Piperoxan
Prazosin
Quinazosin
Quinidine
Silodosin
Spegatrine
Spiperone
Talipexole
Tamsulosin
Terazosin
Tiodazosin
Tolazoline
Tetracyclic antidepressants (e.g.,
amoxapine ,
maprotiline ,
mianserin )
Tricyclic antidepressants (e.g.,
amitriptyline ,
clomipramine ,
doxepin ,
imipramine ,
trimipramine )
Trimazosin
Typical antipsychotics (e.g.,
chlorpromazine ,
fluphenazine ,
loxapine ,
thioridazine )
Urapidil
WB-4101
Zolertine
α2
Agonists Antagonists
1-PP
Adimolol
Amesergide
Aptazapine
Atipamezole
Atypical antipsychotics (e.g.,
asenapine ,
brexpiprazole ,
clozapine ,
lurasidone ,
olanzapine ,
paliperidone ,
quetiapine ,
risperidone ,
zotepine )
Azapirones (e.g.,
buspirone ,
gepirone ,
ipsapirone ,
tandospirone )
BRL-44408
Buflomedil
Cirazoline
Efaroxan
Esmirtazapine
Fenmetozole
Fluparoxan
Idazoxan
Ketanserin
Lisuride
mCPP
Mianserin
Mirtazapine
NAN-190
Pardoprunox
Phentolamine
Phenoxybenzamine
Piperoxan
Piribedil
Rauwolscine
Rotigotine
Setiptiline
Spegatrine
Spiroxatrine
Sunepitron
Terguride
Tolazoline
Typical antipsychotics (e.g.,
chlorpromazine ,
fluphenazine ,
loxapine ,
thioridazine )
Yohimbine
β
mAChRs Tooltip Muscarinic acetylcholine receptors
Agonists
Antagonists
3-Quinuclidinyl benzilate
4-DAMP
Aclidinium bromide (
+formoterol )
Abediterol
AF-DX 250
AF-DX 384
Ambutonium bromide
Anisodamine
Anisodine
Antihistamines (first-generation) (e.g.,
brompheniramine ,
buclizine ,
captodiame ,
chlorphenamine (chlorpheniramine) ,
cinnarizine ,
clemastine ,
cyproheptadine ,
dimenhydrinate ,
dimetindene ,
diphenhydramine ,
doxylamine ,
meclizine ,
mequitazine ,
perlapine ,
phenindamine ,
pheniramine ,
phenyltoloxamine ,
promethazine ,
propiomazine ,
triprolidine )
AQ-RA 741
Atropine
Atropine methonitrate
Atypical antipsychotics (e.g.,
clozapine ,
fluperlapine ,
olanzapine (
+fluoxetine ),
rilapine ,
quetiapine ,
tenilapine ,
zotepine )
Benactyzine
Benzatropine (benztropine)
Benzilone
Benzilylcholine mustard
Benzydamine
BIBN 99
Biperiden
Bornaprine
Camylofin
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
Cyclobenzaprine
Cyclopentolate
Darifenacin
DAU-5884
Desfesoterodine
Dexetimide
DIBD
Dicycloverine (dicyclomine)
Dihexyverine
Difemerine
Diphemanil metilsulfate
Ditran
Drofenine
EA-3167
EA-3443
EA-3580
EA-3834
Emepronium bromide
Etanautine
Etybenzatropine (ethybenztropine)
Fenpiverinium
Fentonium bromide
Fesoterodine
Flavoxate
Glycopyrronium bromide (
+beclometasone/formoterol ,
+indacaterol ,
+neostigmine )
Hexahydrodifenidol
Hexahydrosiladifenidol
Hexbutinol
Hexocyclium
Himbacine
HL-031,120
Homatropine
Imidafenacin
Ipratropium bromide (
+salbutamol )
Isopropamide
J-104,129
Hyoscyamine
Mamba toxin 3
Mamba toxin 7
Mazaticol
Mebeverine
Meladrazine
Mepenzolate
Methantheline
Methoctramine
Methylatropine
Methylhomatropine
Methylscopolamine
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
Oxapium iodide
Oxitropium bromide
Oxybutynin
Oxyphencyclimine
Oxyphenonium bromide
PBID
PD-102,807
PD-0298029
Penthienate
Pethidine
pFHHSiD
Phenglutarimide
Phenyltoloxamine
Pipenzolate bromide
Piperidolate
Pirenzepine
Piroheptine
Pizotifen
Poldine
Pridinol
Prifinium bromide
Procyclidine
Profenamine (ethopropazine)
Propantheline bromide
Propiverine
Quinidine
3-Quinuclidinyl thiochromane-4-carboxylate
Revefenacin
Rociverine
RU-47,213
SCH-57,790
SCH-72,788
SCH-217,443
Scopolamine (hyoscine)
Scopolamine butylbromide (hyoscine butylbromide)
Silahexacyclium
Sofpironium bromide
Solifenacin
SSRIs Tooltip Selective serotonin reuptake inhibitors (e.g.,
femoxetine ,
paroxetine )
Telenzepine
Terodiline
Tetracyclic antidepressants (e.g.,
amoxapine ,
maprotiline ,
mianserin ,
mirtazapine )
Tiemonium iodide
Timepidium bromide
Tiotropium bromide
Tiquizium bromide
Tofenacin
Tolterodine
Tricyclic antidepressants (e.g.,
amitriptyline (
+perphenazine ),
amitriptylinoxide ,
butriptyline ,
cidoxepin ,
clomipramine ,
desipramine ,
desmethyldesipramine ,
dibenzepin ,
dosulepin (dothiepin) ,
doxepin ,
imipramine ,
lofepramine ,
nitroxazepine ,
northiaden (desmethyldosulepin) ,
nortriptyline ,
protriptyline ,
quinupramine ,
trimipramine )
Tridihexethyl
Trihexyphenidyl
Trimebutine
Tripitamine (tripitramine)
Tropacine
Tropatepine
Tropicamide
Trospium chloride
Typical antipsychotics (e.g.,
chlorpromazine ,
chlorprothixene ,
cyamemazine (cyamepromazine) ,
loxapine ,
mesoridazine ,
thioridazine )
Umeclidinium bromide (
+vilanterol )
WIN-2299
Xanomeline
Zamifenacin
Precursors (and
prodrugs )
nAChRs Tooltip Nicotinic acetylcholine receptors
Agonists (and
PAMs Tooltip positive allosteric modulators )
5-HIAA
6-Chloronicotine
A-84,543
A-366,833
A-582,941
A-867,744
ABT-202
ABT-418
ABT-560
ABT-894
Acetylcholine
Altinicline
Anabasine
Anatabine
Anatoxin-a
AR-R17779
Bephenium hydroxynaphthoate
Butinoline
Butyrylcholine
Carbachol
Choline
Cotinine
Cytisine
Decamethonium
Desformylflustrabromine
Dianicline
Dimethylphenylpiperazinium
Epibatidine
Epiboxidine
Ethanol (alcohol)
Ethoxysebacylcholine
EVP-4473
EVP-6124
Galantamine
GTS-21
Ispronicline
Ivermectin
JNJ-39393406
Levamisole
Lobeline
MEM-63,908 (RG-3487)
Morantel
Nicotine (
tobacco )
NS-1738
PHA-543,613
PHA-709,829
PNU-120,596
PNU-282,987
Pozanicline
Pyrantel
Rivanicline
RJR-2429
Sazetidine A
SB-206553
Sebacylcholine
SIB-1508Y
SIB-1553A
SSR-180,711
Suberyldicholine
Suxamethonium (succinylcholine)
Suxethonium (succinyldicholine)
TC-1698
TC-1734
TC-1827
TC-2216
TC-5214
TC-5619
TC-6683
Tebanicline
Tribendimidine
Tropisetron
UB-165
Varenicline
WAY-317,538
XY-4083
Antagonists (and
NAMs Tooltip negative allosteric modulators )
Precursors (and
prodrugs )
H1
Agonists Antagonists
Others:
Atypical antipsychotics (e.g.,
aripiprazole ,
asenapine ,
brexpiprazole ,
brilaroxazine ,
clozapine ,
iloperidone ,
olanzapine ,
paliperidone ,
quetiapine ,
risperidone ,
ziprasidone ,
zotepine )
Phenylpiperazine
antidepressants (e.g.,
hydroxynefazodone ,
nefazodone ,
trazodone ,
triazoledione )
Tetracyclic antidepressants (e.g.,
amoxapine ,
loxapine ,
maprotiline ,
mianserin ,
mirtazapine ,
oxaprotiline )
Tricyclic antidepressants (e.g.,
amitriptyline ,
butriptyline ,
clomipramine ,
desipramine ,
dosulepin (dothiepin) ,
doxepin ,
imipramine ,
iprindole ,
lofepramine ,
nortriptyline ,
protriptyline ,
trimipramine )
Typical antipsychotics (e.g.,
chlorpromazine ,
flupenthixol ,
fluphenazine ,
loxapine ,
perphenazine ,
prochlorperazine ,
thioridazine ,
thiothixene )
H2
H3
H4