70-22-4

Basic information

• Product Name: OXOTREMORINE
• Synonyms: 2’-oxopyrrolidino-1-pyrrolidino-4-butyne;oxotremorin;1-(4-(pyrrolidin-1-yl)but-2-ynyl)pyrrolidin-2-one;1-(2-Oxo-pyrrolidin-1-yl)-4-(pyrrolidin-1-yl)-2-butyne;1-(2-Oxopyrrolidin-1-yl)-4-(pyrrolidin-1-yl)-2-butyne;1-[4-(Pyrrolidin-1-yl)-2-butynyl]pyrrolidin-2-one;1-(4-pyrrolidin-1-ylbut-2-ynyl)-2-pyrrolidone;1-(4-(Pyrrolidin-1-yl)but-2-yn-1-yl)pyrrolidin-2-one
• CAS NO: 70-22-4
• Molecular Formula: C₁₂H₁₈N₂O
• Molecular Weight: 206.28
• EINECS: 200-728-0
• Mol File: 70-22-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 124 °C0.1 mm Hg(lit.)
• Flash Point: 113 °C
• Appearance: clear, light yellow/liquid
• Density: 1 g/mL at 25 °C(lit.)
• Vapor Pressure: 8.7E-06mmHg at 25°C
• Refractive Index: n20/D 1.517(lit.)
• Storage Temp.: 2-8°C
• Solubility: H2O: 50 mg/mL
• Merck: 13,7020
• CAS DataBase Reference: OXOTREMORINE(CAS DataBase Reference)
• NIST Chemistry Reference: OXOTREMORINE(70-22-4)
• EPA Substance Registry System: OXOTREMORINE(70-22-4)

Safety Data

• Hazard Codes: T+,C
• Statements: 28-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2810 6.1/PG 1
• WGK Germany: 3
• RTECS: UY5950100
• F: 10-23
• HazardClass: 6.1(a)
• PackingGroup: I
• Hazardous Substances Data: 70-22-4(Hazardous Substances Data)

Usage

General Description

Oxotremorine [1-(-pyrrolidono)-4-pyrrolidino-2-butyne] has been regarded as a CNS muscarinicstimulant. Its action on the brain produces tremors inexperimental animals. It increases ACh brain levels in ratsup to 40% and has been studied as a drug in the treatment ofAlzheimer disease. Although earlier studies suggested thatthis approach of elevating levels of ACh to treat Alzheimerdisease is useful, this belief was highly disputed by manyresearchers.

Clinical Use

Nevertheless, oxotremorine, as a cholinergicagonist, facilitates memory storage. These findings haveserved as important leads in the development of agents usefulin treating Alzheimer disease. Although it possessesgroups that do not occur in other highly active muscarinicagents, oxotremorine’s trans conformation shows that distancesbetween possible active centers correspond with (+)-muscarine.

Safety Profile

Poison by ingestion and intraperitoneal routes. Moderately toxic by intravenous route. When heated to decomposition it emits toxic fumes of NOx.

InChI:InChI=1/C12H18N2O/c15-12-6-5-11-14(12)10-4-3-9-13-7-1-2-8-13/h1-2,5-11H2

Upstream product

• 123-75-1 pyrrolidine 
• 50-00-0 formaldehyd 
• 766-61-0 1-prop-2-ynyl-pyrrolidin-2-one 

Downstream Products

• 3922-00-7 N-[4-(1-pyrrolidinyl)-2-butenyl]-pyrrolidinone 
• 14052-94-9 N-(4-Pyrrolidinobutyl)-2-pyrrolidon 

Relevant articles and documents

SPIRO NITROGEN-BRIDGED HETEROCYCLIC COMPOUNDS

The invention relates to novel compounds (I) for treating diseases of the central and peripheral nervous system: STR1 including enantiomers, racemates and acid addition and quaternary salts thereof, wherein one of X and Y is O and the other of X and Y is N; Q is (CH 2) n or C(CH. sub.3) 2 where n is 1, 2 or 3 and the bridge--Q--is attached at one end to position 1 and at the other end to position 4 or 5, and R° is hydrogen, methyl or hydroxyl; in the moiety STR2 the line connecting Z and Y signifies a double bond when X--Z is O--C--R and Y is N, and a single bond when X--Z is N=C--R and Y is O; Z is C--R wherein R is selected from hydrogen, NH 2, NH-R" (R"=C 1-6-alkyl) , N(R") 2, R", C 2-6-alkenyl, C 2-6-alkynyl, C 3-7-cycloalkyl, R" substituted by hydroxy or by 1-6 halogen atoms, R"O-C 1-6-alkyl, carboxy-C 1-6-alkyl, R"OCO-C 1-6-alkyl, amino-C 1-6-alkyl, R"NH-C 1-6-alkyl, (R") 2 N-C 1-6-alkyl, 2-oxo-pyrrolidin-1-ylmethyl, aryl, diarylmethylol, and R" substituted by one or two aryl groups, wherein aryl denotes phenyl optionally substituted by 1-3 halogens, R", R"O and(or) CF 3. Also claimed are compounds wherein the line connecting Z and Y signifies the absence of a bond, X is O, Z is H and Y is NH 2, NO 2 or N 3. "