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All 9 posts   Subject: Nordiazepam & Nitrazepam   Please login to post   Down

 
    Megatherium
(Hive Bee)
10-23-03 22:44
No 466412
      Nordiazepam & Nitrazepam
(Rated as: excellent)
    

Nordiazepam

Patent DE1136709
JOC (1961) vol 26 p 4936
JOC (1962) vol 27 p 562


Nitrazepam

Patent US3109843
Patent US3116203
Patent US3123529
Patent DE1136709
Patent DE1145626
JMC (1963) vol 6 p 261
 
 
 
 
    Rhodium
(Chief Bee)
10-24-03 16:26
No 466525
User Picture 
      Nordiazepam & Nitrazepam
(Rated as: excellent)
    

That's a good complement to these writeups by the late PsychoChemist:

Nordiazepam (https://www.rhodium.ws/chemistry/nordiazepam.html)
Nitrazepam (https://www.rhodium.ws/chemistry/nitrazepam.html)

Here are the above listed articles:

Nitrazepam

Quinazolines and 1,4-Benzodiazepines. X. Nitro-Substituted 5-Phenyl-1,4-benzodiazepine Derivatives
L. H. Sternbach, R. Ian Fryer, O. Keller, W. Metlesics, G. Sach, N. Steiger
J. Med. Chem. 6, 261-265 (1963) (https://www.rhodium.ws/pdf/benzodiazepines-10.nitrazepam.pdf)

Abstract
The general synthesis of nitro-substituted 1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-ones from aminonitrobenzophenones and the specific synthesis of 1,3-dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-ones by direct nitration of the corresponding unsubstituted benzodiaxepinones is described. The position of the nitro group was proved by its replacement by chlorine via a Sandmeyer reaction of the amine obtained by reduction. Alkylation of some of the benzodiazepinones gave the corresponding 1-alkyl derivatives. Mild acid hydrolysis of nitrobenzodiazepinones and 1-alkyl-nitrobenzodiazepinones led to several previously undescribed aminonitrobenzophenones. 2-Amino-5-nitrobenzophenone was converted aia the a-oxime into the corresponding 2-chloromethyl-6-nitro-4-phenylquinazoline 3-oxide and this compound when treated with nucleophilic reagents gave, by a ring expansion, 1,3-dihydro-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one 4-oxide. The pharmacological properties of three nitrobenzodiazepine derivatives are reported. These compounds showed a low toxicity combined with sedative, muscle relaxant and anticonvulsant properties.


Nordiazepam

Quinazolines and 1,4-Benzodiazepines. IV. Transformations of 7-Chloro-2-methylamino-5-phenyl-3H-1,4-benzodiazepine 4-Oxide
L. H. Sternbach, E. Reeder
J. Org. Chem. 26, 4936-4941 (1961) (https://www.rhodium.ws/pdf/benzodiazepines-04.nordiazepam.pdf)

Abstract
7-Chloro-2-methylamino-5-phenvl-3H-1,4-benzodiazepine 4-oxide (I) and its acetyl derivative (II) can be hydrolyzed to 7-chloro-5-phenyl-3H-1,4-benzodiazepin-2(1H)-one 4-oxide (III). Other methods are described for the synthesis of this compound and its conversion into pharmacologically active beneodiazepinones.


1,3-Dihydro-2H-1,4-benzodiazepine-2-ones and Their 4-Oxides
S. C. Bell, T. S. Sulkowski, C. Gochman, S. J. Childress
J. Org. Chem. 27, 562-566 (1962) (https://www.rhodium.ws/pdf/benzodiazepine-2-ones.nordiazepam.pdf)

Abstract
Alcoholic sodium hydroxide converts 6-chloro-2-chloromethyl-4-phenylquinazoline 3-oxide (I) into 7-chloro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepine-2-one 4-oxide (II). 7-Chloro-5-phenyl-1,3-dihydro-2H-1,4benzodiazepine-2-one (III) was prepared by reduction of II and by several alternate routes. A number of analogs were made.
 
 
 
 
    Megatherium
(Hive Bee)
10-25-03 12:45
No 466678
      Thanks, now we 've got the articles online :-)     

Thanks, now we 've got the articles online smile.

In the future, there is more to come about the zepams.
 
 
 
 
    eXcidium
(Stranger)
02-02-04 17:22
No 486061
      Such as a full synthesis Of Flunitrazepam? ;)     

Such as a full synthesis Of Flunitrazepam? ;)

Let God Die And Rot
 
 
 
 
    Megatherium
(Hive Bee)
02-26-04 19:29
No 491267
      Post deleted on request     

(empty)
 
 
 
 
    Tricky
(Stunning)
02-26-04 19:53
No 491270
      offtopic :)     

Rated by me as terrible offtopic!

Sorry, it's not about chemistry...
Only my own opinion.
Flunitrazepame is more dangerous then all opioids all together...

Sorry for all I said above, cause I tried this shit on my own skin...

-who dares, wins-
 
 
 
 
    Megatherium
(Hive Bee)
02-27-04 03:36
No 491336
      Off-topic?     

Why is a reference to the patents of flunitrazepam off-topic?

Pharmacologically speaking, flunitrazepam is a hypnotic - just like nitrazepam, and unlike nordazepam which is a anxiolytic.   Flunitrazepam is more potent (dose being 1 - 2 mg) than nitrazepam (dose = 5 mg) though.

Second, I only answered the question:
Such as a full synthesis Of Flunitrazepam? ;)

If my chemical appropriate answer is ought to be off-topic, why wasn't the above question rated that way to begin with?  It could just as well have saved me the effort to find the information.

Well, I just deleted the post & hope everybody can sleep well now  wink.
 
 
 
 
    starlight
(Hive Bee)
02-27-04 11:05
No 491390
      own post     

i think he was referring to his own post as off topic.
 
 
 
 
    Rhodium
(Chief Bee)
09-20-04 21:49
No 532376
User Picture 
      Review Article: 1,4-Benzodiazepines
(Rated as: excellent)
    

Review Article:
1,4-Benzodiazepines

Scott J. Childress & M.I. Gluckman
J. Pharm. Sci. 53(6), 577-590 (1964) (https://www.rhodium.ws/pdf/1.4-benzodiazepines.review.pdf)

The Hive - Clandestine Chemists Without Borders
 
 

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