From Wikipedia, the free encyclopedia
WIN-2299
Names
Preferred IUPAC name
2-(Diethylamino)ethyl cyclopentyl(hydroxy)(thiophen-2-yl)acetate
Identifiers
ChemSpider
ECHA InfoCard
100.035.835
EC Number
InChI=1S/C17H27NO3S/c1-3-18(4-2)11-12-21-16(19)17(20,14-8-5-6-9-14)15-10-7-13-22-15/h7,10,13-14,20H,3-6,8-9,11-12H2,1-2H3
Key: ASXBIKGZCPZCAN-UHFFFAOYSA-N
InChI=1/C17H27NO3S/c1-3-18(4-2)11-12-21-16(19)17(20,14-8-5-6-9-14)15-10-7-13-22-15/h7,10,13-14,20H,3-6,8-9,11-12H2,1-2H3
Key: ASXBIKGZCPZCAN-UHFFFAOYAH
O=C(OCCN(CC)CC)C(O)(C1CCCC1)C2=CC=CS2
Properties
C 17 H 27 N O 3 S
Molar mass
325.47 g·mol−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
WIN-2299 is an anticholinergic drug.[ 1] Human reactions to WIN-2299 include sedation (2 mg), LSD -like reactions (6 mg), and an acute delirious episode (10 mg).[ 2]
^ Luduena, FP; Lands, AM (1954). "An investigation of the pharmacological actions of three potent antispasmodic compounds and their corresponding metho-salts". The Journal of Pharmacology and Experimental Therapeutics . 110 (3): 282– 92. PMID 13143475 .
^ Pennes, HH; Hoch, PH (1957). "Psychotomimetics, clinical and theoretical considerations: Harmine, Win-2299 and nalline". The American Journal of Psychiatry . 113 (10): 887– 92. doi :10.1176/ajp.113.10.887 . PMID 13402982 .
Psychedelics (5-HT2A agonists)
Benzofurans Lyserg‐ amides Phenethyl‐ amines
2C-x
3C-x 4C-x DOx HOT-x MDxx Mescaline (subst.) TMAs
TMA
TMA-2
TMA-3
TMA-4
TMA-5
TMA-6
Others
Piperazines Tryptamines
alpha -alkyltryptaminesx -DALT x -DET x -DiPT x -DMT
4,5-DHP-DMT
2,N,N-TMT
4-AcO-DMT
4-HO-5-MeO-DMT
4,N,N-TMT
4-Propionyloxy-DMT
5,6-diBr-DMT
5-AcO-DMT
5-Bromo-DMT
5-MeO-2,N ,N -TMT
5-MeO-4,N ,N -TMT
5-MeO-α,N,N-TMT
5-MeO-DMT
5-N ,N -TMT
7,N,N-TMT
α,N,N-TMT
(Bufotenin) 5-HO-DMT
DMT
Norbaeocystin
(Psilocin) 4-HO-DMT
(Psilocybin) 4-PO-DMT
x -DPT Ibogaine-related x -MET x -MiPT Others
Others
Dissociatives (NMDAR antagonists )
Deliriants (mAChR antagonists ) Others
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
Bevonium
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 )