Propylhexedrine

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Structural formula
Structure of propylhexedrine
( R ) -isomer (left) and ( S ) -isomer (right)
General
Non-proprietary name Propylhexedrine
other names
  • (2-Cyclohexyl-1-isopropyl) methylamine ( IUPAC )
Molecular formula C 10 H 21 N
External identifiers / databases
CAS number
  • 101-40-6 (unspec.)
  • 3595-11-7 (racemate)
  • 6192-98-9 (hydrochloride)
EC number 202-939-3
ECHA InfoCard 100.002.673
PubChem 7558
DrugBank DB06714
Wikidata Q408704
Drug information
Drug class

Sympathomimetic

properties
Molar mass 155.28 g mol −1
density

0.85 g cm −3 (25 ° C)

Melting point
  • 127–128 ° C [(±) -hydrochloride]
  • 138–139 ° C (hydrochloride enantiomers)
boiling point
  • 80–81 ° C (1.2 k Pa , S -enantiomer)
  • 92–93 ° C (2.7 kPa, racemate)
pK s value

4.78 (pK b )

solubility

Slightly soluble in water, miscible with ethanol , chloroform and diethyl ether

safety instructions
GHS hazard labeling
no classification available
Toxicological data

70 mg kg −1 ( LD 50 ,  mouse ,  ip , (±) -hydrochloride)

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Propylhexedrine (also hexahydrodeoxyephedrine) is a central nervous system stimulant marketed in the United States as the Benzedrex inhaler pen . Propylhexedrine is structurally related to methamphetamine .

It is mainly used for the symptomatic treatment of nasal discharge from colds and allergies .

The ( S ) enantiomer , also known as levopropylhexedrine , is also used as an appetite suppressant . The salt of the ( S ) -enantiomer with phenobarbital gives the antiepileptic drug barbexaclone .

synthesis

Propylhexedrine can be produced by the nuclear hydrogenation of methamphetamine in the presence of platinum (IV) oxide as a catalyst :

Synthesis of propylhexedrine

An enantiomer separation can with the help of L - tartaric acid - (+) take place.

Individual evidence

  1. ↑ a b c d The Merck Index : An Encyclopedia of Chemicals, Drugs, and Biologicals . 14th edition. Merck & Co., Whitehouse Station NJ 2006, ISBN 978-0-911910-00-1 , pp. 1350-1351.
  2. ↑ a b c Entry on levopropylhexedrine. In: Römpp Online . Georg Thieme Verlag, accessed on November 15, 2014.
  3. ^ LG Chatten, LE Harris: Relationship between pKb (H2O) of Organic Compounds and E 1∕2 Values ​​in Several Nonaqueous Solvents. , in: Anal. Chem. 1962 , 34 , 1495-1501; doi : 10.1021 / ac60191a041 .
  4. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  5. ^ A. Kleemann, J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications, 4th Edition, Thieme 2001, ISBN 3-13-115134-X .
  6. ↑ Lands, AM; Nash, VL; Granger, HR; Dertinger, BL: The Pharmacologic Activity of N-Methyl-β-cyclohexylisopropylamine Hydrochloride in J. Pharmacol. Exp. Ther. 89 (1947) 382-385.
  7. ↑ External identifiers or database links for levopropylhexedrine : CAS number: 6192-97-8, EC number: 228-245-0, ECHA InfoCard: 100.025.678 , PubChem : 71197 , ChemSpider : 64333 , Wikidata : Q15409406 .
  8. ↑ BL Zenitz, EB Macks, ML Moore: Preparation of Some Primary and Secondary β-Cyclohexylalkylamines in J. Am. Chem. Soc. 69 (1947) 1117-1121. doi : 10.1021 / ja01197a039
  9. ↑ Patent US2454746 : Cyclohexylalkylamines. Filed May 13, 1947 , published November 23, 1948 , Applicant: Smith, Kline & French Labor, Inventor: Glenn E. Ullyot. ‌