CS-27349

CS-27349

Identifiers
IUPAC name (1R,2R,5S)-8-Methyl-8-azabicyclooct-2-yl hydroxy(diphenyl)acetate
CAS Number	64471-12-1 Y HCl: 64520-33-8
PubChem CID	3049185 HCl: 3049184
ChemSpider	143123 HCl: 57264798
ChEMBL	ChEMBL298138
CompTox Dashboard (EPA)	DTXSID70983033 HCl: DTXSID90983151
Chemical and physical data
Formula	C22H25NO3
Molar mass	351.446 g·mol−1
3D model (JSmol)	Interactive image
SMILES CN1C2CC(C1CC2)OC(=O)C(C3=CC=CC=C3)(C4=CC=CC=C4)O.Cl
InChI InChI=1S/C22H25NO3/c1-23-18-12-14-19(23)20(15-13-18)26-21(24)22(25,16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18-20,25H,12-15H2,1H3/t18?,19?,20-/m1/s1 Key:LSJGAYNIIMEDLR-SOAGJPPSSA-N

CS-27349, or L-2-α-tropinyl benzilate, is an experimental incapacitating agent. It acts as an antagonist to muscarinic acetylcholine receptors, causing delirium. It has 37% of the potency of the related compound 3-quinuclidinyl benzilate (BZ) in producing peripheral effects, but 85% of the potency in producing central effects. The mean dose required to incapacitate subjects was 1.2 times that of BZ. It has not been in use since the 1970s, and there have been no publications about its effects or long-term toxicology since then.

References

1. ^ Ball JC (2015). "Dual Use Research of Concern: Derivatives of 3-Quinuclidinyl Benzilate". Military Medical Science Letters. 84 (1): 2–41. doi:10.31482/mmsl.2015.001.
2. ^ Assessment of Potential Long-Term Health Effects on Army Human Test Subjects of Relevant Biological and Chemical Agents, Drugs, Medications and Substances (PDF) (Report). Ho-Chunk Technical Solutions Healthcare Division. February 29, 2016. Archived (PDF) from the original on December 25, 2020.

v t e Agents used in chemical warfare incapacitation riot control
Blood agents	Cyanogen Cyanogen bromide Cyanogen chloride (CK) Hydrogen cyanide (AC) Arsine Cacodyl cyanide Cacodyl oxide Hydrogen sulfide Phosphine Carbon monoxide Phosphorus trifluoride Methyl cyanoformate Iron pentacarbonyl Nickel tetracarbonyl 2,3,7,8-Tetrachlorodibenzodioxin Glycolonitrile Lactonitrile Acetone cyanohydrin Stibine Chloral cyanohydrin
Blister agents	Arsenicals Ethyldichloroarsine (ED) Methyldichloroarsine (MD) Phenyldichloroarsine (PD) Lewisite (L) Lewisite 2 (L2) Lewisite 3 (L3) Sulfur mustards Levinstein mustard (EA-229) T Q CEES Nitrogen mustards HN1 HN2 HN3 TL-301 Nettle agents Phosgene oxime (CX) Other KB-16 Dibutylchloromethyltin chloride Selenium oxychloride
Nerve agents	G-agents Tabun (GA) Sarin (GB) Chlorosarin (ClGB) Thiosarin (SGB) Soman (GD) Chlorosoman (ClGD) Ethylsarin (GE) GH Cyclosarin (GF) GP Fluorotabun EA-1356 EA-4352 Crotylsarin V-agents EA-2192 EA-3148 VE VG VM VP VR VS VX EA-1763 Chinese VX V-sub x (GD-7) GV agents GV (EA-5365) Novichok agents A-208 A-232 A-234 A-242 A-262 C01-A035 C01-A039 C01-A042 Carbamates Dimethylcarbamoyl fluoride EA-3887 EA-3887A EA-3966 EA-3990 EA-4056 T-1123 T-1152 T-1194 Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide) TL-599 TL-1238 TL-1299 TL-1317 Miotine (AR-28/T-1843) 3152 CT 4-686-293-01 (Agent 1-10) Other Diisopropyl fluorophosphate Dicyclohexyl phosphorofluoridate EA-2012 EA-2054 EA-2098 EA-2613 2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate Neopentylene fluorophosphate Selenophos Phospholine R-16661 Ro 3-0422 Methanesulfonyl fluoride Dimefox (TL-792) MSPI Precursors Acetonitrile AT ATO AlP A.P.C. complex Chlorosarin Chlorosoman Cyclohexanol 1,8-Dibromooctane N,N-Diisopropylaminoethanol (KB) EA-1250 DIHP ZS DEHP EA-1224 Dimethylamidophosphoric dichloride Dimethylamidophosphoric dicyanide DMHP Ethylphosphonoselenoic dichloride Formaldoxime Nital 4-Hydroxycoumarin Isopropyl alcohol (TB) Methyldichlorophosphine (SW) Methylphosphonyl difluoride (difluoro) (DF) Methylphosphonyl dichloride (dichloro) Nitromethane OPA mixture Phosphoryl chloride Phosphorus pentachloride Phosphorus trichloride (TH) Pinacolone Pinacolyl alcohol Phenacyl chloride QL 2,4,5-Trichlorophenol 3,3,5-Trimethylcyclohexanol Triethyl phosphite Trimethyl phosphite TC TG
Neurotoxins	Anatoxin-a Saxitoxin (TZ) Bungarotoxin Botulinum toxin (BTX) Tetanospasmin (TeNT) Ryanodine Ciguatoxin (CTX) Guanitoxin (GTX) Chlorophenylsilatrane Palytoxin (PTX) Maitotoxin (MTX) Tetrodotoxin Aconitine Brevetoxin (PbTX) Strychnine Antillatoxin (ATX) Tetraethyllead Dimethylmercury HN1 hydrochloride HN2 hydrochloride HN3 hydrochloride A-8564 Picrotoxin Sulfuryl fluoride Tremorine Oxotremorine Batrachotoxin Tetramethylenedisulfotetramine (TETS) Bicyclic phosphates IPTBO TBPO TBPS Cloflubicyne Trimethylolpropane phosphite Domoic acid
Pulmonary/ choking agents	Chlorine Bromine Phosgene (CG) Fluorine Perfluoroisobutene Chloropicrin (PS) Dimethyl(trifluoromethylthio)arsine Diphosgene (DP) Disulfur decafluoride (Z) Acrolein Ethyl bromoacetate Perchloromethyl mercaptan Phenylcarbylamine chloride Tetranitromethane Tetrachlorodinitroethane Chlorine trifluoride Perchloryl fluoride Cadmium oxide Cadmium chloride Mercuric chloride Selenium dioxide Selenoyl fluoride Trifluoronitrosomethane Trichloronitrosomethane Nitric oxide Nitrogen dioxide Dinitrogen tetroxide Sulfur dioxide Phosphorus trichloride Methyl isocyanate Ethenone Methyl vinyl ketone Trifluoroacetyl chloride Salcomine Fluomine Uranium hexafluoride Diborane Green Cross
Vomiting agents	Adamsite (DM) Chloropicrin Litharge-glycerine Diphenylchlorarsine Diphenylcyanoarsine Cacodyl cyanide o-Dianisidine
Incapacitating agents	BZ (CS-4030) Apomorphine Butyrophenone EA-4941 (CS-4640) Etorphine EA-2092 CS-4297 Etoxadrol Dimethylheptylpyran (DMHP) EA-2148 EA-3167 EA-3443 Pethidine EA-3580 Ibogaine EA-3834 Kolokol-1 LSD-25 PAVA spray Psilocybin Sleeping gas Carfentanil JB-318 JB-336 CS-27349 CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,668 Benperidol Desflurane Enflurane Bufotenin Isoflurane Halothane Sevoflurane Pentazocine Procarbazine Fluphenazine Chlorpromazine
Lachrymatory agents	Xylyl bromide Pepper spray (OC) Mace (spray) CN CS CR CNS Benzyl chloride Benzyl bromide Benzyl iodide Bromobenzyl cyanide Thiophosgene Chloroacetone Bromoacetone Bromomethyl ethyl ketone Acrolein Phenacyl bromide Chloroacetophenone oxime Ethyl bromoacetate Ethyl iodoacetate Iodoacetone Allyl isothiocyanate Hexamethylene diisocyanate Crotonaldehyde
Malodorant agents	Thioacetone Allicin Skatole Cadaverine Putrescine
Cornea-clouding agents	Lewisite CX KB-16 Methyl cyanoacrylate N-Methylmorpholine Allyl alcohol Osmium tetroxide Acrolein
Biological toxins	Abrin Aconitine Cyclopiazonic acid Histrionicotoxins Aflatoxins Anatoxin-a Batrachotoxin Botulinum toxin Brevetoxin Ciguatoxin Domoic acid Enterotoxin type B Grayanotoxin Guanitoxin Maitotoxin Modeccin Palytoxin Ricin Saxitoxin Shiga toxin T-2 mycotoxin Tetanospasmin Tetrodotoxin Volkensin Veratridine
Other	Methyl fluoroacetate Napalm (variants and mixtures) Fluoroethyl fluoroacetate Depleted uranium post-combustion uranium oxides Plutonium and its compounds Polonium White phosphorus
List of chemical warfare agents CB military symbol

v t e Hallucinogens
Psychedelics (5-HT2A agonists)	Benzofurans 2C-B-FLY 2CBFly-NBOMe 5-MeO-BFE 5-MeO-DiBF Bromo-DragonFLY F-2 F-22 TFMFly Lyserg‐ amides 1B-LSD 1cP-LSD 1P-ETH-LAD 1P-LSD 1cP-AL-LAD 1cP-MiPLA 1V-LSD 2-Butyllysergamide 3-Pentyllysergamide AL-LAD ALD-52 BU-LAD Diallyllysergamide Dimethyllysergamide ECPLA Ergometrine ETH-LAD IP-LAD LAE-32 LAMPA LPD-824 LSA LSD LSD-Pip LSH LSM-775 LSZ Methylergometrine MIPLA Methysergide MLD-41 PARGY-LAD PRO-LAD Phenethyl‐ amines 2C-x 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V 25x-NBx 25x-NB 25B-NB 25C-NB 25x-NB3OMe 25B-NB3OMe 25C-NB3OMe 25D-NB3OMe 25E-NB3OMe 25H-NB3OMe 25I-NB3OMe 25N-NB3OMe 25P-NB3OMe 25T2-NB3OMe 25T4-NB3OMe 25T7-NB3OMe 25TFM-NB3OMe 25x-NB4OMe 25B-NB4OMe 25C-NB4OMe 25D-NB4OMe 25E-NB4OMe 25H-NB4OMe 25I-NB4OMe 25N-NB4OMe 25P-NB4OMe 25T2-NB4OMe 25T4-NB4OMe 25T7-NB4OMe 25TFM-NB4OMe 25x-NBF 25B-NBF 25C-NBF 25D-NBF 25E-NBF 25H-NBF 25I-NBF 25P-NBF 25T2-NBF 25T7-NBF 25TFM-NBF 25x-NBMD 25B-NBMD 25C-NBMD 25D-NBMD 25E-NBMD 25F-NBMD 25H-NBMD 25I-NBMD 25P-NBMD 25T2-NBMD 25T7-NBMD 25TFM-NBMD 25x-NBOH 25B-NBOH 25C-NBOH 25CN-NBOH 25D-NBOH 25E-NBOH 25F-NBOH 25H-NBOH 25I-NBOH 25P-NBOH 25T2-NBOH 25T7-NBOH 25TFM-NBOH 25x-NBOMe 25B-NBOMe 25C-NBOMe 25CN-NBOMe 25D-NBOMe 25E-NBOMe 25F-NBOMe 25G-NBOMe 25H-NBOMe 25I-NBOMe 25iP-NBOMe 25N-NBOMe 25P-NBOMe 25T-NBOMe 25T2-NBOMe 25T4-NBOMe 25T7-NBOMe 25TFM-NBOMe Atypical structures 25B-N1POMe 25B-NAcPip 25B-NB23DM 25B-NB25DM 25C-NBCl 25C-NBOEt 25C-NBOiPr 25I-N2Nap1OH 25I-N3MT2M 25I-N4MT3M 25I-NB34MD 25I-NBAm 25I-NBBr 25I-NBMeOH 25I-NBTFM 2CBCB-NBOMe 2CBFly-NBOMe 4-EA-NBOMe 5-APB-NBOMe 5MT-NBOMe C30-NBOMe DOB-NBOMe DOI-NBOMe FECIMBI-36 MDPEA-NBOMe N-Ethyl-2C-B NBOMe-escaline NBOMe-mescaline ZDCM-04 25x-NMx 25B-NMe7BF 25B-NMe7BT 25B-NMe7Bim 25B-NMe7Box 25B-NMe7DHBF 25B-NMe7Ind 25B-NMe7Indz 25B-NMePyr 25I-NMe7DHBF 25I-NMeFur 25I-NMeTHF 25I-NMeTh N-(2C)-fentanyl N-(2C-B) fentanyl N-(2C-C) fentanyl N-(2C-D) fentanyl N-(2C-E) fentanyl N-(2C-G) fentanyl N-(2C-H) fentanyl N-(2C-I) fentanyl N-(2C-IP) fentanyl N-(2C-N) fentanyl N-(2C-P) fentanyl N-(2C-T) fentanyl N-(2C-T-2) fentanyl N-(2C-T-4) fentanyl N-(2C-T-7) fentanyl N-(2C-TFM) fentanyl 3C-x 3C-AL 3C-BZ 3C-DFE 3C-E 3C-MAL 3C-P 4C-x 4C-B 4C-C 4C-D 4C-E 4C-I 4C-N 4C-P 4C-T-2 DOx DOT DOB DOC DOEF DOET DOF DOI DOiPR DOM DON DOPR DOTFM MEM HOT-x HOT-2 HOT-7 HOT-17 MDxx DMMDA DMMDA-2 Lophophine MDA MDAI MDBZ MDMA MMDA MMDA-2 MMDA-3a MMDMA Mescaline (subst.) 2-Bromomescaline 3-TE 4-TE 3-TM 4-TM Allylescaline Asymbescaline Buscaline Cyclopropylmescaline Difluoromescaline Difluoroescaline Escaline Fluoroproscaline Isobuscaline Isoproscaline Jimscaline Mescaline Metaescaline Methallylescaline Proscaline Thioproscaline Trifluoroescaline Trifluoromescaline TMAs TMA TMA-2 TMA-3 TMA-4 TMA-5 TMA-6 Others 2C-B-BUTTERFLY 2C-B-DragonFLY 2C-B-DragonFLY-NBOH 2C-B-FLY-NB2EtO5Cl 2CB-5-hemifly 2CB-Ind 2CD-5EtO 2-TOET 5-TOET 2-TOM 5-TOM BOB BOD βk-2C-B βk-2C-I DESOXY DMCPA DMBMPP DOB-FLY Fenfluramine Ganesha Macromerine MMA TCB-2 TOMSO Piperazines 2C-B-PP BZP pFPP Tryptamines alpha-alkyltryptamines 4,5-DHP-α-MT 5-MeO-α-ET 5-MeO-α-MT α-ET α-MT x-DALT (Daltocin) 4-HO-DALT (Daltacetin) 4-AcO-DALT 5-MeO-DALT DALT x-DET (Ethacetin) 4-AcO-DET (Ethocin) 4-HO-DET 5-MeO-DET (T-9) DET (Ethocybin) 4-PO-DET x-DiPT (Ipracetin) 4-AcO-DiPT (Iprocin) 4-HO-DiPT 5-MeO-DiPT 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 (Depracetin) 4-AcO-DPT (Deprocin) 4-HO-DPT 5-MeO-DPT (The Light) DPT Ibogaine-related 18-MAC 18-MC Coronaridine Ibogaine Ibogamine ME-18-MC Noribogaine Tabernanthine Voacangine x-MET (Metocin) 4-HO-MET (Metocetin) 4-AcO-MET 5-MeO-MET MET x-MiPT (Mipracetin) 4-AcO-MiPT (Miprocin) 4-HO-MiPT 5-Me-MiPT (Moxy) 5-MeO-MiPT MiPT Others 4-HO-DBT 4-HO-EPT 4-HO-McPT (Lucigenol) 4-HO-MPMI (Meprocin) 4-HO-MPT 5-MeO-EiPT 5-MeO-MALT 5-MeO-MPMI Aeruginascin Baeocystin DBT DCPT EiPT EPT MPT PiPT Others AL-38022A ALPHA Dimemebfe Efavirenz Glaucine Lorcaserin M-ALPHA RH-34 Also empathogens in general (e. g.: 5-APB, 5-MAPB, 6-APB and other substituted benzofurans).
Dissociatives (NMDAR antagonists)	Arylcyclo‐ hexylamines Ketamine-related 2-Fluorodeschloroketamine Arketamine ((R)-ketamine) Deschloroketamine Ethketamine (N-Ethylnorketamine) Esketamine ((S)-ketamine) Ketamine Methoxetamine Methoxmetamine Methoxyketamine MXiPr Norketamine Tiletamine PCP-related 2'-Oxo-PCE 3-HO-PCP 3-MeO-PCE 3-MeO-PCMo 3-MeO-PCP 4-MeO-PCP BDPC Dieticyclidine (PCDE) Eticyclidine (PCE) PCPr Phencyclidine (PCP) Rolicyclidine (PCPy) Tenocyclidine (TCP) Others BTCP Gacyclidine PRE-084 Adamantanes Amantadine Memantine Rimantadine Diarylethylamines Diphenidine Ephenidine Fluorolintane Methoxphenidine Morphinans Dextrallorphan Dextromethorphan Dextrorphan Racemethorphan Racemorphan Others 2-EMSB 2-MDP 8A-PDHQ Aptiganel Budipine Delucemine Dexoxadrol Dizocilpine Etoxadrol Herkinorin Ibogaine Midafotel NEFA Neramexane Nitrous oxide Noribogaine Perzinfotel RB-64 Remacemide Selfotel Xenon
Deliriants (mAChR antagonists)	Atropine Benactyzine Benzatropine Benzydamine Biperiden BRN-1484501 Brompheniramine BZ CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,368 CAR-302,537 CAR-302,668 Chloropyramine Chlorphenamine Clemastine CS-27349 Cyclizine Cyproheptadine Dicycloverine Dimenhydrinate Diphenhydramine Ditran Doxylamine EA-3167 EA-3443 EA-3580 EA-3834 Flavoxate Hyoscyamine JB-318 JB-336 Meclozine Mepyramine Orphenadrine Oxybutynin Pheniramine Phenyltoloxamine Procyclidine Promethazine Scopolamine Tolterodine Trihexyphenidyl Tripelennamine Triprolidine WIN-2299
Others	Cannabinoids (CB1 agonists) Natural Salvinorin A THC (Dronabinol) THCV Synthetic AM-x AM-087 AM-251 AM-279 AM-281 AM-356 AM-374 AM-381 AM-404 AM-411 AM-630 AM-661 AM-678 AM-679 AM-694 AM-735 AM-855 AM-881 AM-883 AM-905 AM-906 AM-919 AM-926 AM-938 AM-1116 AM-1172 AM-1220 AM-1221 AM-1235 AM-1241 AM-1248 AM-1710 AM-1714 AM-1902 AM-2201 AM-2212 AM-2213 AM-2232 AM-2233 AM-2389 AM-3102 AM-4030 AM-4054 AM-4056 AM-4113 AM-6545 CP x CP 47,497 CP 55,244 CP 55,940 (±)-CP 55,940 (+)-CP 55,940 (-)-CP 55,940 HU-x HU-210 HU-211 HU-239 HU-243 HU-308 HU-320 HU-331 HU-336 HU-345 JWH-x JWH-007 JWH-015 JWH-018 JWH-019 JWH-030 JWH-047 JWH-048 JWH-051 JWH-057 JWH-073 JWH-081 JWH-098 JWH-116 JWH-120 JWH-122 JWH-133 JWH-139 JWH-147 JWH-148 JWH-149 JWH-149 JWH-161 JWH-164 JWH-166 JWH-167 JWH-171 JWH-175 JWH-176 JWH-181 JWH-182 JWH-184 JWH-185 JWH-192 JWH-193 JWH-194 JWH-195 JWH-196 JWH-197 JWH-198 JWH-199 JWH-200 JWH-203 JWH-205 JWH-210 JWH-210 JWH-213 JWH-220 JWH-229 JWH-234 JWH-249 JWH-250 JWH-251 JWH-253 JWH-258 JWH-300 JWH-302 JWH-307 JWH-336 JWH-350 JWH-359 JWH-387 JWH-398 JWH-424 Misc. designer cannabinoids 4-HTMPIPO 5F-AB-FUPPYCA 5F-AB-PINACA 5F-ADB 5F-ADB-PINACA 5F-ADBICA 5F-AMB 5F-APINACA 5F-CUMYL-PINACA 5F-NNE1 5F-PB-22 5F-SDB-006 A-796,260 A-836,339 AB-001 AB-005 AB-CHFUPYCA AB-CHMINACA AB-FUBINACA AB-PINACA ADAMANTYL-THPINACA ADB-CHMINACA ADB-FUBINACA ADB-PINACA ADBICA ADSB-FUB-187 AMB-FUBINACA APICA APINACA APP-FUBINACA CB-13 CUMYL-PICA CUMYL-PINACA CUMYL-THPINACA DMHP EAM-2201 FAB-144 FDU-PB-22 FUB-144 FUB-APINACA FUB-JWH-018 FUB-PB-22 FUBIMINA JTE 7-31 JTE-907 Levonantradol MDMB-CHMICA MDMB-CHMINACA MDMB-FUBINACA MEPIRAPIM MAM-2201 MDA-19 MN-18 MN-25 NESS-0327 NESS-040C5 Nabilone Nabitan NM-2201 NNE1 Org 28611 Parahexyl PTI-1 PTI-2 PX-1 PX-2 PX-3 QUCHIC QUPIC RCS-4 RCS-8 SDB-005 SDB-006 STS-135 THC-O-acetate THC-O-phosphate THJ-018 THJ-2201 UR-144 WIN 55,212-2 XLR-11 D2 agonists Apomorphine Aporphine Bromocriptine Cabergoline Lisuride LSD Memantine Nuciferine Pergolide Phenethylamine Piribedil Pramipexole Ropinirole Rotigotine Salvinorin A Also indirect D2 agonists, such as dopamine reuptake inhibitors (cocaine, methylphenidate), releasing agents (amphetamine, methamphetamine), and precursors (levodopa). GABAA enhancers CI-966 Eszopiclone Ibotenic acid Muscimol (Amanita muscaria) Zaleplon Zolpidem Zopiclone Inhalants (Mixed MOA) Aliphatic hydrocarbons Butane Gasoline Kerosene Propane Aromatic hydrocarbons Toluene Ethers Diethyl ether Enflurane Haloalkanes Chlorofluorocarbons Chloroform κOR agonists 2-EMSB Alazocine Bremazocine Butorphan Butorphanol Cyclazocine Cyclorphan Cyprenorphine Diprenorphine Enadoline Herkinorin Heroin HZ-2 Ibogaine Ketazocine Levallorphan Levomethorphan Levorphanol LPK-26 Metazocine Morphine Nalbuphine Nalmefene Nalorphine Noribogaine Oxilorphan Pentazocine Phenazocine Proxorphan Racemethorphan Racemorphan Salvinorin A Spiradoline Tifluadom U-50488 U-69,593 Xorphanol Oneirogens Calea zacatechichi Silene capensis Galantamine Others Glaucine Isoaminile Noscapine Prenoxdiazine Pukateine

v t e Muscarinic acetylcholine receptor modulators
mAChRsTooltip Muscarinic acetylcholine receptors	Agonists 77-LH-28-1 AC-42 AC-260,584 Aceclidine Acetylcholine AF30 AF150(S) AF267B Alvameline AQRA-741 Arecoline Bethanechol Bevonium Butyrylcholine Carbachol CDD-0034 CDD-0078 CDD-0097 CDD-0098 CDD-0102 Cevimeline Choline cis-Dioxolane Clozapine Desmethylclozapine (norclozapine) Ethoxysebacylcholine Itameline LY-593,039 L-689,660 LY-2,033,298 McNA343 Methacholine Milameline Muscarine NGX-267 Ocvimeline Oxotremorine PD-151,832 Pilocarpine RS86 Sabcomeline SDZ 210-086 Sebacylcholine Suberyldicholine Talsaclidine Tazomeline Thiopilocarpine Vedaclidine VU-0029767 VU-0090157 VU-0152099 VU-0152100 VU-0238429 WAY-132,983 Xanomeline YM-796 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 SSRIsTooltip 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)	Acetyl-coA Adafenoxate Choline (lecithin) Citicoline Cyprodenate Dimethylethanolamine Glycerophosphocholine Meclofenoxate (centrophenoxine) Phosphatidylcholine Phosphatidylethanolamine Phosphorylcholine Pirisudanol
See also Receptor/signaling modulators Nicotinic acetylcholine receptor modulators Acetylcholine metabolism/transport modulators

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