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Doxapram

Product Name
Doxapram
CAS No.
309-29-5
Chemical Name
Doxapram
Synonyms
ahr619;Dopram;dopream;AHR-619;DOXOPRAM;DOXAPRAM;Respiram;Doxapram USP/EP/BP;DOPRAM; STIMULEX; RESPIRAM;Doxapram (AHR-619, Dopram, Stimulex or Respiram)
CBNumber
CB4245654
Molecular Formula
C24H30N2O2
Formula Weight
378.51
MOL File
309-29-5.mol
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Doxapram Property

Melting point:
113 - 114°C
Boiling point:
506.58°C (rough estimate)
Density 
1.1056 (rough estimate)
refractive index 
1.5620 (estimate)
storage temp. 
2-8°C
solubility 
Chloroform (Slightly), Methanol (Slightly)
form 
Solid
pka
7.30±0.10(Predicted)
color 
White to Off-White
NIST Chemistry Reference
2-Pyrrolidinone, 1-ethyl-4-[2-(4-morpholinyl)ethyl]-3,3-diphenyl-(309-29-5)
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Safety

Hazardous Substances Data
309-29-5(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H317May cause an allergic skin reaction

H319Causes serious eye irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TRC
Product number
D552505
Product name
Doxapram
Packaging
5mg
Price
$85
Updated
2021/12/16
Usbiological
Product number
447681
Product name
Doxapram
Packaging
5mg
Price
$360
Updated
2021/12/16
Matrix Scientific
Product number
090576
Product name
1-Ethyl-4-(2-morpholinoethyl)-3,3-diphenylpyrrolidin-2-one
Purity
95+%
Packaging
250mg
Price
$492
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0002484
Product name
DOXAPRAM
Purity
95.00%
Packaging
1G
Price
$1080.45
Updated
2021/12/16
Matrix Scientific
Product number
090576
Product name
1-Ethyl-4-(2-morpholinoethyl)-3,3-diphenylpyrrolidin-2-one
Purity
95+%
Packaging
1g
Price
$1092
Updated
2021/12/16
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Doxapram Chemical Properties,Usage,Production

Originator

Dopram,Robins,US,1965

Uses

Doxapram HCl inhibits TASK-1, TASK-3, TASK-1/TASK-3 heterodimeric channel function with EC50 of 410 nM, 37 μM, 9 μM, respectively - See more at: http://www.selleckchem.com/products/doxapram-hcl.html#sthash.SSt04Hwr.dpuf

Uses

Doxapram increases the rate and depth of respiration. It is used for post-anesthetic respiratory depression, and for respiratory depression caused by drug use.

Uses

Doxapram is a central respiratory stimulant.

Definition

ChEBI: A member of the class of pyrrolidin-2-ones that is N-ethylpyrrolidin-2-one in which both of the hydrogens at the 3 position (adjacent to the carbonyl group) are substituted by phenyl groups, and one of the hydrogens at the 4 position is ubstituted by a 2-(morpholin-4-yl)ethyl group. A central and respiratory stimulant with a brief duration of action, it is used (generally as the hydrochloride or the hydrochloride hydrate) as a temporary treatment of acute respiratory failure, particularly when superimposed on chronic obstructive pulmonary disease, and of postoperative respiratory depression. It has also been used for treatment of postoperative shivering.

Manufacturing Process

(A) Preparation of α-(1-ethyl-3-pyrrolidyl)-α,α-diphenylacetonitrile: A suspension of the sodium salt of diphenylacetonitrile was formed by the dropwise addition at 50°C of 193 grams (1.0 mol) of diphenylacetonitrile to a stirred suspension of 43 grams (1.1 mols) of sodium amide in 1 liter of dry toluene. After addition was complete, the mixture was refluxed for 4 hours and then, to the refluxing mixture, 1.0 mol of 1-ethyl-3-chloropyrrolidine was added at a rapid dropwise rate with continuous stirring. After addition was complete, stirring and refluxing were continued for 3 hours. The mixture was then cooled and extracted with one normal hydrochloric acid. The aqueous layer together with an oil layer were separated, made basic with dilute sodium hydroxide, and extracted with ether. The ethereal solution was dried over sodium sulfate and concentrated and the residue was distilled in vacuo. The material crystallized from a 4:1 ethanol-water mixture.
(B) Preparation of 4-(β-chloroethyl)-3,3-diphenyl-1-ethyl-2-pyrrolidinone: A solution of α,α-diphenyl-α-(1-ethyl-3-pyrrolidyl)-acetonitrile in 70% sulfuric acid was heated at 130-140°C for 48 hours, poured onto ice, made basic with sodium hydroxide, and extracted with chloroform. The chloroform solution was acidified with hydrogen chloride gas, dried over sodium sulfate and concentrated. The residue was refluxed in 500 ml of thionyl chloride for 3 hours; the resulting solution was concentrated in vacuo; and the residue wascrystallized from isopropyl ether.
(C) Preparation of doxapram hydrochloride [3,3-diphenyl-1-ethyl-4-(2- morpholino-ethyl)-2-pyrrolidinone hydrochloride monohydrate]: A solution of 25 grams (0.076 mol) of 4-(2-chloroethyl)-3,3-diphenyl-1-ethyl-2- pyrrolidinone and 13.3 grams (0.153 mol) of morpholine in 500 ml of absolute ethanol was heated at 95°-120°C for 21 hours in a closed system and concentrated in vacuo. The residue was dissolved in 300 ml of two normal hydrochloric acid and extracted with 150 ml of ethyl acetate. A solid crystallized (13 g) during the extraction and was removed by filtration. MP 217°-219°C. The acid extracts were made basic with sodium hydroxide and extracted with ether, and the ether solution was concentrated in vacuo and the residue was suspended in six normal hydrochloric acid. Additional crystalline product formed and was recrystallized from two normal hydrochloric acid. Yield, 10 grams; MP 217°-219°C. Total yield, 23 grams (70%).

Therapeutic Function

Respiratory stimulant

Synthesis

Doxapram, 1-ethyl-4-(2-morpholinoethyl)-3,3-diphenyl-2-pyrrolidinone (8.2.4), is synthesized in the following manner. Diphenylacetonitrile in the presence of sodium amide is alkylated with 1-ethyl-3-chlorpyrrolidine, giving (1-ethyl-3-pyrrolidinyl) diphenylacetonitrile (8.2.1). Acidic hydrolysis of the nitrile group gives (1-ethyl-3 pyrrolidinyl)diphenylacetic acid (8.2.2). Reacting this with phosphorous tribromide (thionyl chloride, thionyl bromide, acetic anhydride) leads to rearrangement with an opening of the pyrrolidine ring and the subsequent closing of the pyrrolidinone ring, forming 1-ethyl-4-(2-bromoethyl)-3,3-diphenyl-2-pyrrolidinone (8.2.3). Substitution of the bromine atom with a morpholine group gives doxapram (8.2.4) [15¨C18].

Doxapram Preparation Products And Raw materials

Raw materials

Preparation Products

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Doxapram Suppliers

Alsachim SAS
Tel
--
Fax
--
Email
sales@alsachim.com
Country
France
ProdList
424
Advantage
0
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View Lastest Price from Doxapram manufacturers

Dideu Industries Group Limited
Product
Doxapram 309-29-5
Price
US $1.10/g
Min. Order
1g
Purity
99.9%
Supply Ability
100 Tons min
Release date
2021-07-28
Career Henan Chemical Co
Product
Doxapram 309-29-5
Price
US $1.00/KG
Min. Order
1KG
Purity
≥98%
Supply Ability
g/kg/Ton
Release date
2019-12-25

309-29-5, DoxapramRelated Search:


  • 1-Ethyl-4-[2-(4-morpholinyl)ethyl]-3,3-diphenyl-2-pyrrolidinone
  • 2-Pyrrolidinone, 1-ethyl-4-(2-morpholinoethyl)-3,3-diphenyl-
  • ahr619
  • AHR-619
  • Dopram
  • dopream
  • 2-Pyrrolidinone, 1-ethyl-4-(2-morpholinoethyl)-3,3-diphenyl- (7CI, 8CI)
  • 2-Pyrrolidinone, 1-ethyl-4-[2-(4-morpholinyl)ethyl]-3,3-diphenyl-
  • DOXOPRAM
  • 1-Ethyl-4-(2-morpholin-4-ylethyl)-3,3-di(phenyl)pyrrolidin-2-one
  • 1-Ethyl-4-(2-morpholinoethyl)-3,3-diphenyl-2-pyrrolidone
  • 1-Ethyl-4-(2-morpholinoethyl)-3,3-diphenylpyrrolidin-2-one
  • 4-(2-chloroethyl)-1-ethyl-3,3-diphenylpyrrolidin-2-one
  • 1-ethyl-4-(2-(4-morpholinyl)ethyl)-3,3-diphenyl-2-pyrrolidinon
  • 1-ethyl-4-(2-morpholinoethyl)-3,3-diphenyl-2-pyrrolidinon
  • 1-Ethyl-4-(2-morpholinoethyl)-3,3-diphenyl-2-pyrrolidinone
  • DOXAPRAM
  • DOPRAM; STIMULEX; RESPIRAM
  • Respiram
  • Doxapram USP/EP/BP
  • Doxapram (AHR-619, Dopram, Stimulex or Respiram)
  • 309-29-5
  • Pharmaceutical