155058-71-2

Basic information

• Product Name: (+/-)-TROPANYL 2-(4-CHLOROPHENOXY)BUTANOATE MALEATE
• Synonyms: SM-21 MALEATE;SM21;(+/-)-TROPANYL 2-(4-CHLOROPHENOXY)BUTANOATE MALEATE;TROPANYL 2-(4-CHLOROPHENOXY)BUTANOATE MALEATE;TROPINE 2-(4-CHLOROPHENOXY)BUTANOATE MALEATE SALT;WTPAXDRULIZRDJ-SSGZVVCFSA-N
• CAS NO: 155058-71-2
• Molecular Formula: C₁₈H₂₄ClNO₃
• Molecular Weight: 453.91
• Mol File: 155058-71-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 425°Cat760mmHg
• Flash Point: 210.9°C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 1.97E-07mmHg at 25°C
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (+/-)-TROPANYL 2-(4-CHLOROPHENOXY)BUTANOATE MALEATE(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-TROPANYL 2-(4-CHLOROPHENOXY)BUTANOATE MALEATE(155058-71-2)
• EPA Substance Registry System: (+/-)-TROPANYL 2-(4-CHLOROPHENOXY)BUTANOATE MALEATE(155058-71-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 155058-71-2(Hazardous Substances Data)

Usage

Uses

SM-21 is a potent and selective σ2 antagonist, increasing release of ACh.

Biological Activity

Potent and selective σ 2 antagonist with central effects following systemic administration. Causes increased release of acetylcholine at central muscarinic synapses. Potent analgesic (efficacy comparable to morphine) and nootropic agent.

InChI:InChI=1/C18H24ClNO3.C4H4O4/c1-3-17(22-15-8-4-12(19)5-9-15)18(21)23-16-10-13-6-7-14(11-16)20(13)2;5-3(6)1-2-4(7)8/h4-5,8-9,13-14,16-17H,3,6-7,10-11H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1-

Upstream product

• 56895-14-8 2-(4-Chlorophenoxy)butyric acid chloride 
• 120-29-6 3-tropanol 
• 106-48-9 4-chloro-phenol 
• 34385-92-7 2-(4-chlorophenoxy)butanoic acid 

Relevant articles and documents

Presynaptic cholinergic modulators as potent cognition enhancers and analgesic drugs. 2. 2-Phenoxy-, 2-(phenylthio)-, and 2-(phenylamino)alkanoic acid esters

Further modifications of the leads ((R)-(+)-hyoscyamine and (p- chlorophenyl)propionic acid α-tropanyl ester), which show analgesic and nootropic activities as a consequence of increased central presynaptic ACh release, are reported. 2-Phenoxy- and 2-(phenylthio)alkanoic acid esters showed the best results. Several members of these classes possess analgesic properties which are comparable to that of morphine and at the same time are able to reverse dicyclomine-induced amnesia. Confirmation was found that the mechanism of action is due to an increase in ACh release at central muscarinic synapses and that both auto- and heteroreceptors controlling ACh release are very likely involved. According to the results obtained with (R)- (+)-hyoscyamine, analgesic activity is stereochemistry dependent, since the R-(+)-enantiomers are always more efficacious than the corresponding S-(-)- ones. On the basis of their potency and acute toxicity, compounds (±)-28 (SM21) and (±)-42 (SM32) were selected for further study.