Author Topic: Sedative Ureides  (Read 2865 times)

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Bwiti

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Sedative Ureides
« on: October 17, 2004, 10:16:00 PM »
Carbromal(Uradal, Adalin)
1 mole of ?-bromo-?-ethyl butyryl bromide is mixed with dry urea(1 mole) and heated on a steam bath for several hours. Precautions must be taken to keep steam and atmospheric H2O from the reaction vessel. Cool, allow to solidify, wash with H2O, and recrystallize from alcohol. Dose: (sedative) 300 to 500mg, (hypnotic) 700 to 950mg, mp 116-118°C. This drug is less potent than the barbiturates, but it is less toxic, extremely well tolerated, has a wide margin of safety, and acts rapidly.

Bromural(Bromovaletone)
This is made the same way that carbromal is made, except that the intermediate is ?-bromo-isovaleryl bromide. The 1 to 1 molar ratio and everything else remains unchanged Yields colorless crystals, mp: 147-149°C. This is a rapid-action, short-duration hypnotic. It is well tolerated and has a low toxicity. Dose: 300-600mg.

Reference: “Recreational Drugs” by Professor Buzz

These synths are so easy that even Professor Buzz can’t fuck them up!

Are either bromo-intermediates easily obtainable? I can’t find my merck index CD, and a patent search at

http://ch.espacenet.com/espacenet/ch/en/e_net.htm

didn’t turn-up dick, so I’m wondering how they’re made, do they have any synonyms, what their properties are? Are there other ureides or analogs that could possibly have sedative effects? Peace! 8)


Rhodium

  • Guest
The synthesis of Bromural and its precursors
« Reply #1 on: October 18, 2004, 12:12:00 AM »
The synthesis of Bromural and its precursors can be found on page 999 in

Vogel's "Practical Organic Chemistry", 3rd Ed

(https://www.thevespiary.org/rhodium/Rhodium/chemistry/vogel3.html)

The precursor ?-bromoacyl bromides are likely not commercially available, and has to be made from the corresponding carboxylic acid through the well-known

Hell-Volhard-Zelinsky Reaction

(http://www.organic-chemistry.org/namedreactions/hell-volhard-zelinsky-reaction.shtm)


Bwiti

  • Guest
couldn't find..
« Reply #2 on: October 18, 2004, 05:58:00 PM »
Page 999 of Vogel's 3rd edition had nothing on the chem of interest, and the Hell-Volhard-Zelinsky Reaction is useless to the simple chemist.


Rhodium

  • Guest
Bromural - Bromisovalum
« Reply #3 on: October 21, 2004, 01:42:00 AM »
The synthesis is definitely on

page 999 in Vogel's "Pracical Organic Chemistry"

(https://www.thevespiary.org/rhodium/Rhodium/djvu/vogel/practical-organic-chem_224_0001_2.djvu)

Here it follows (minus footnotes and pointers to equipment & precursor preparation):


IX,4. Bromural (?-Bromo-Isovalerylurea)

Iso-Valeric acid is converted by phosphorus and bromine into ?-bromo-isovaleryl bromide; the latter upon heating with urea gives bromural.

Bromural

Equip a 1 litre bolt-head flask with dropping funnel and a double surface reflux condenser; to the top of the latter attach a device for the absorption of the hydrogen bromide evolved.

Place 100 g. (108 ml.) of dry iso-valeric acid and 12 g of purified red phosphorus in the flask. Add 255 g (82 ml) of dry bromine slowly through the dropping funnel at such a rate that little or no bromine is lost with the hydrogen bromide evolved; the addition occupies 2-3 hours. Warm the reaction mixture on a water bath until the evolution of hydrogen bromide is complete and the colour of the bromine has disappeared. Pour off the liquid reaction product into a Claisen flask and distil under the reduced pressure of a water pump. Collect the ?-bromo-iso-valeryl bromide at 117-122°C/25-30 mm. The yield is 150g.

In a 500 ml. bolt-head flask provided with a thermometer (reaching almost to the bottom) and a calcium chloride (or cotton wool) guard tube, place 100g of ?-bromo-iso-valeryl bromide and 50g of dry, finely divided urea. Start the reaction by warming the flask on a water bath; the temperature soon rises to about 80°C. Maintain this temperature for about 3 hours; the mass will liquefy and then resolidify. Transfer the sticky reaction product to a large beaker containing saturated sodium bicarbonate solution, stir mechanically and add more saturated sodium bicarbonate solution in small quantities until effervescence ceases. Filter at the pump, suck as dry as possible and dry the crude bromural upon filter paper in the air. Recrystallise the dry product from toluene. Alternatively, recrystallise the moist product from hot water (ca. 700 ml). The yield of pure bromural, m.p. 154-155°C, is 28 g.




Bonus - Forensic article on a sedative Ureide:


Sensitive and selective determination of bromisovalum by HPLC/particle beam mass spectrometry
T. Nagata, K. Kudo, T. Imamura & N. Jitsufuchi, Forensic Sci. Int. 74(3), 205-211 (1995)



Abstract
A specific procedure using high-performance liquid chromatography/particle beam mass spectrometry (HPLC/PBMS) has facilitated determination of bromisovalum in human plasma and whole blood. Bromisovalum, a sedative and hypnotic, was effectively extracted with SepPak C18 cartridges and selectively determined by HPLC/PBMS of EI mode. An originally synthesized 2-bromohexanoylurea served as the internal standard (IS). The calibration curve was linear over the concentration range 0.5-5.0 µg/g and the lower limit of detection was 0.1 µg/g (10 ng at the time of direct injection). This method could be practically applied to detect bromisovalum in the whole blood of an autopsied individual.







Captain_America

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bwiti
« Reply #4 on: October 21, 2004, 04:39:00 AM »
How would you describe the effects of this compound?

Bwiti

  • Guest
shit..
« Reply #5 on: October 25, 2004, 11:34:00 AM »
Oops! The menu above took me to the right place just as long as I selected 1024 as the destination page.. Would the compounds of chloro or iodo be easier to get? I've paid for custom synthesis twice so far, but I can't afford it lately. Any analogue ideas, that include easier to obtain precursors. I'm guessing that no one will help, but it's worth a try. Fuck! Peace tomorrow, hell today. 8)