Dextromoramide

from Wikipedia, the free encyclopedia
Structural formula
Structural formula of dextromoramide
General
Non-proprietary name Dextromoramide
other names

(3 R ) -3-methyl-4- (morpholin-4-yl) -2,2-diphenyl-1- (pyrrolidin-1-yl) butan-1-one ( IUPAC )

Molecular formula
  • C 25 H 32 N 2 O 2
  • C 25 H 32 N 2 O 2 · C 4 H 6 O 6 ( bitartrate )
External identifiers / databases
CAS number
  • 357-56-2
  • 2922-44-3 ( bitartrate )
EC number 206-613-1
ECHA InfoCard 100.006.013
PubChem 92943
ChemSpider 83901
DrugBank DB01529
Wikidata Q408446
Drug information
ATC code

N02 AC01

Drug class

Analgesics

properties
Molar mass 392.53 g · mol -1
Physical state

firmly

Melting point

180-184 ° C

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling
no classification available
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dextromoramide is a strong synthetic pain reliever with an opiate-like effect. The drug was launched in 1957 by Janssen Pharmaceutica under the tradename Palfium .

The substance is a derivative of 3,3-diphenylpropylamine and belongs to the methadone group. In contrast to methadone, the molecule contains a morpholine and a pyrrolidine ring.

Extraction and presentation

The synthesis of dextromoramide starts from diphenylacetyl chloride, which is first converted into the corresponding acid amide with pyrrolidine. After reaction with sodium amide and 4- (2-chloropropyl) morpholine, this gives the racemic (±) -moramid (racemoramid). A racemate resolution using D - tartaric acid leads to the enantiomerically pure target compound:

Synthesis of dextromoramide

The (3 S ) -enantiomer levomoramide obtained in the resolution is pharmacologically inactive.

Legal situation

According to the Narcotics Act in the Federal Republic of Germany, dextromoramide has been a marketable, but not a prescription, narcotic drug since 1993 .

literature

  • HJ Bochnik: Development of addiction and severe withdrawal symptoms after use of dextromoramide (Jetrium, MCP 875, Palfium, R 875, Errecalme, Pyrrolamidol). In: Archiv für Toxikologie , Vol. 18 (No. 3), 1960, pp. 170-176.
  • HJ Roth and H. Fenner: Medicines. Thieme, Stuttgart and New York 1988, pp. 336-343.

Individual evidence

  1. ↑ Entry on dextromoramide. In: Römpp Online . Georg Thieme Verlag, accessed on June 16, 2014.
  2. ↑ a b Janssen, PAJ; Janssen, JC: A New Series of Potent Analgesics in J. Am. Chem. Soc. 78 (1956) 3862-3862, doi: 10.1021 / ja01596a087 .
  3. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  4. ↑ a b c d e f A. Kleemann , J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications , 4th Edition, Thieme-Verlag, Stuttgart 2000, ISBN 978-1-58890- 031-9 .
  5. ↑ Patents BE 544 757, DE 1 117 126, GB 822 055 (Janssen 1956).
  6. ↑ Paul AJ Janssen, Anton H. Jageneau: A New Series of Potent Analgesics: DEXTRO 2: 2-Diphenyl-3-methyl-4-morpholinobutyrylpyrrolidine and Related Amides Part I. Chemical Structure and Pharmacological Activity . In: Journal of Pharmacy and Pharmacology . tape 9 , no. 1 , September 1957, p. 381-400 , doi : 10.1111 / j.2042-7158.1957.tb12290.x .
  7. ↑ Fourth Amendment to Narcotics Law - 4th BtMÄndV, of December 23, 1992 .

Trade names

Jetrium (D - no longer available), Palfium (D - no longer available, NL ), Palface (NL)