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

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

Uses

Used in Pharmaceutical Research:
Oxotremorine is used as a research compound for studying the effects of muscarinic stimulation on the central nervous system. Its ability to increase ACh levels in the brain makes it a valuable tool for investigating the role of acetylcholine in cognitive function and neurodegenerative diseases.
Used in Alzheimer's Disease Research:
Oxotremorine is used as a potential therapeutic agent in the study and treatment of Alzheimer's disease. It has been explored as a means to elevate ACh levels in the brain, which was initially thought to be a promising approach for managing the disease. However, the effectiveness of this approach remains a subject of debate among researchers.
Used in Toxicological Studies:
Due to its ability to induce tremors in experimental animals, Oxotremorine is also used in toxicological studies to understand the effects of muscarinic stimulation on the nervous system and to develop potential countermeasures or treatments for exposure to similar compounds.

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. "

Cholinergic activity of acetylenic imidazoles and related compounds

A series of acetylenic imidazoles related to oxotremorine (1a) were prepared and evaluated as cholinergic agents with in vitro binding assays and in vivo pharmacological tests in mice. 1-[4-(1H-Imidazol-1-yl)-2-butynyl]-2-pyrrolidinone (1b) was a cholinergic agonist with one-half the potency of oxotremorine. Analogues of 1b with a 5- or 2-methyl substituent in the imidazole ring (compounds 1c and 1g) were cholinergic partial agonists. Analogues of 1b with a methyl substituent at the 5-position in the pyrrolidinone ring (7b) or at the α-position in the acetylenic chain (8b) were antagonists. Various analogues of these imidazole acetylenes where the pyrrolidinone ring was replaced by an amide, carbamate, or urea residue were prepared. Several compounds which contained 5-methylimidazole as the amine substituent were partial agonists. The activities of the imidazole compounds are compared with those of the related pyrrolidine and dimethylamine analogues. Agonist and antagonist conformations for these compounds at muscarinic receptors are proposed.