S33005 Other names (–)-1-(1-dimethylaminomethyl) 5-methoxybenzocyclobutan-1-yl) cyclohexanol
1-[7-[(dimethylamino)methyl]-4-methoxy-7-bicyclo[4.2.0]octa-1(6),2,
4-trienyl]cyclohexan-1-ol
CAS Number PubChem CID ChemSpider UNII Formula C 18 H 27 N O 2 Molar mass 289.419 g·mol−1 3D model (JSmol )
CN(C)CC1(CC2=C1C=C(C=C2)OC)C3(CCCCC3)O
InChI=1S/C18H27NO2/c1-19(2)13-17(18(20)9-5-4-6-10-18)12-14-7-8-15(21-3)11-16(14)17/h7-8,11,20H,4-6,9-10,12-13H2,1-3H3
Key:UBIQMAFTTDZGEX-UHFFFAOYSA-N
S33005 is a serotonin–norepinephrine reuptake inhibitor (SNRI) that was under development by Servier for the treatment of depression and related disorders. It is structurally related to venlafaxine but has a more complex molecular structure. Venlafaxine appears to be a sigma modulator,[1] but it is not known if S33005 shares this activity.
Synthesis [ ]
"The 1-cyano-benzocyclobutenes used as starting material are obtained, for example, by subjecting a β-[orthohalogeno-phenyl]-propionitrile to intramolecular condensation in the presence of potassium amide , or by brominating a benzocyclobutene in position 1 with N -bromosuccinimide , followed by exchange of the bromine atom for a cyano group by means of sodium cyanide ."[2]
See also [ ]
References [ ]
External links [ ]
Antidepressants (N06A )
SSRIs
Citalopram
Escitalopram
Fluoxetine #
Fluvoxamine
Indalpine ‡
Paroxetine
Sertraline
Zimelidine ‡
SNRIs
Desvenlafaxine
Duloxetine
Levomilnacipran
Milnacipran
Tofenacin
Venlafaxine
NRIs
Atomoxetine
Reboxetine
Viloxazine
NDRIs
Amineptine ‡
Bupropion
Nomifensine ‡
NaSSAs SARIs
Etoperidone
Nefazodone
Trazodone
SMS Others
Tricyclic and tetracyclic antidepressants
TCAs TeCAs
Amoxapine
Maprotiline
Mianserin
Mirtazapine
Setiptiline
Others
Monoamine oxidase inhibitors
Non-selective MAOA -selectiveMAOB -selective
Adjunctive therapies
Atypical antipsychotics (aripiprazole , brexpiprazole , lurasidone , olanzapine , quetiapine , risperidone )
Buspirone
Lithium (lithium carbonate , lithium citrate )
Thyroid hormones (triiodothyronine (T3 ), levothyroxine (T4 ))
Miscellaneous
Ademetionine (SAMe )
Hypericum perforatum (St. John's Wort)
Oxitriptan (5-HTP )
Rubidium chloride (RbCl)
Tryptophan
# WHO-EM
‡ Withdrawn from market
Clinical trials :
† Phase III
§ Never to phase III
Anxiolytics (N05B )
5-HT1A R agonists GABAA R PAMs
Benzodiazepines : Adinazolam
Alprazolam
Bromazepam
Camazepam
Chlordiazepoxide
Clobazam
Clonazepam
Clorazepate
Clotiazepam
Cloxazolam
Diazepam #
Ethyl loflazepate
Etizolam
Fludiazepam
Halazepam
Ketazolam
Lorazepam #
Medazepam
Nordazepam
Oxazepam
Pinazepam
Prazepam ; Others: Alpidem ‡
Barbiturates (e.g., phenobarbital )
Carisoprodol
Carbamates (e.g., meprobamate )
Chlormezanone ‡
Ethanol (alcohol)
Etifoxine
Imepitoin ; Herbs:
Kava
Skullcap
Valerian
Gabapentinoids (α2 δ VDCC blockers )
Gabapentin
Gabapentin enacarbil
Phenibut
Pregabalin
Antidepressants
SSRIs (e.g., escitalopram )
SNRIs (e.g., duloxetine )
SARIs (e.g., trazodone )
TCAs (e.g., clomipramine # )
TeCAs (e.g., mirtazapine )
MAOIs (e.g., phenelzine ); Others: Agomelatine
Bupropion
Tianeptine
Vilazodone
Vortioxetine
Sympatholytics (Antiadrenergics )
Alpha-1 blockers (e.g., prazosin )
Alpha-2 agonists (e.g., clonidine , dexmedetomidine , guanfacine )
Beta blockers (e.g., propranolol )
Others
# WHO-EM
‡ Withdrawn from market
Clinical trials :
† Phase III
§ Never to phase III
Monoamine reuptake inhibitors
DAT (DRIs )
Piperazines: DBL-583
GBR-12783
GBR-12935
GBR-13069
GBR-13098
Nefazodone
Vanoxerine
Pyrrolidines: Diphenylprolinol
MDPV
Naphyrone
Prolintane
Pyrovalerone
NET (NRIs )
Tetracyclic antidepressants: Amoxapine
Maprotiline
Mianserin
Oxaprotiline
Setiptiline
Others: Antihistamines (e.g., brompheniramine , chlorphenamine , pheniramine , tripelennamine )
Antipsychotics (e.g., loxapine , ziprasidone )
Arylcyclohexylamines (e.g., ketamine , phencyclidine )
Dopexamine
Ephenidine
Ginkgo biloba
Indeloxazine
Nefazodone
Opioids (e.g., desmetramadol , methadone , pethidine (meperidine) , tapentadol , tramadol , levorphanol )
SERT (SRIs )
Others:
Amoxapine
Antihistamines (e.g., brompheniramine , chlorphenamine , dimenhydrinate , diphenhydramine , mepyramine (pyrilamine) , pheniramine , tripelennamine )
Antipsychotics (e.g., loxapine , ziprasidone )
Arylcyclohexylamines (e.g., 3-MeO-PCP , esketamine , ketamine , methoxetamine , phencyclidine )
Cyclobenzaprine
Delucemine
Dextromethorphan
Dextrorphan
Efavirenz
Hypidone
Medifoxamine
Mesembrine
Mifepristone
MIN-117 (WF-516)
N-Me-5-HT
Opioids (e.g., dextropropoxyphene , methadone , pethidine (meperidine) , levorphanol , tapentadol , tramadol )
Roxindole
VMATs
Amiodarone
Amphetamines (e.g., amphetamine , methamphetamine , MDMA )
Bietaserpine
Deserpidine
Deutetrabenazine
Dihydrotetrabenazine
Efavirenz
GBR-12935
Ibogaine
Ketanserin
Lobeline
Reserpine
Rose bengal
Tetrabenazine
Valbenazine
Vanoxerine (GBR-12909)
Others
DAT modulators: Agonist-like: SoRI-9804
; Antagonist-like: SoRI-20041
See also: Receptor/signaling modulators • Monoamine releasing agents • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins
σ1
Agonists: 3-PPP
4-PPBP
5-MeO-DMT
Alazocine (SKF-10047)
Amantadine
Arketamine
BD-1052
Blarcamesine
Captodiame
Citalopram
CGRP
Cloperastine
Cocaine
Cutamesine (SA-4503)
Cyclazocine
Dehydroepiandrosterone (DHEA) (prasterone )
Dehydroepiandrosterone sulfate (DHEA-S) (prasterone sulfate )
Dextrallorphan
Dextromethorphan (DXM)
Dextrorphan (DXO)
Dimemorfan
Dimethyltryptamine (DMT)
Ditolylguanidine (DTG)
Donepezil
Eliprodil
Escitalopram
Fabomotizole (afobazole)
Fluoxetine
Fluvoxamine
Ifenprodil
Igmesine (JO-1784)
Ketamine
L-687384
MDMA (midomafetamine)
Memantine
Methamphetamine
Methoxetamine
Methylphenidate
Nepinalone
Neuropeptide Y
Noscapine
Opipramol
Pentazocine
Pentoxyverine (carbetapentane)
PRE-084
Pregnenolone
Pregnenolone sulfate
Pridopidine
Racemethorphan (methorphan)
Racemorphan (morphanol)
Allosteric modulators: Phenytoin ; Positive: Methylphenylpiracetam
σ2 Unsorted
Antagonists:
Lamotrigine
Naloxone
Allosteric modulators: SKF-83959
See also: Receptor/signaling modulators