Author Topic: Nordiazepam & Nitrazepam  (Read 2498 times)

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Megatherium

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Nordiazepam & Nitrazepam
« on: October 24, 2003, 12:44:00 AM »
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

  • Guest
Nordiazepam & Nitrazepam
« Reply #1 on: October 24, 2003, 06:26:00 PM »
That's a good complement to these writeups by the late PsychoChemist:

Nordiazepam

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

Nitrazepam

(https://www.thevespiary.org/rhodium/Rhodium/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.thevespiary.org/rhodium/Rhodium/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.thevespiary.org/rhodium/Rhodium/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.thevespiary.org/rhodium/Rhodium/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

  • Guest
Thanks, now we 've got the articles online :-)
« Reply #2 on: October 25, 2003, 02:45:00 PM »
Thanks, now we 've got the articles online  :) .

In the future, there is more to come about the zepams.

eXcidium

  • Guest
Such as a full synthesis Of Flunitrazepam? ;)
« Reply #3 on: February 02, 2004, 06:22:00 PM »
Such as a full synthesis Of Flunitrazepam? ;)


Megatherium

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Post deleted on request
« Reply #4 on: February 26, 2004, 08:29:00 PM »
(empty)

Tricky

  • Guest
offtopic :)
« Reply #5 on: February 26, 2004, 08:53:00 PM »
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...


Megatherium

  • Guest
Off-topic?
« Reply #6 on: February 27, 2004, 04:36:00 AM »
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   ;) .

starlight

  • Guest
own post
« Reply #7 on: February 27, 2004, 12:05:00 PM »
i think he was referring to his own post as off topic.

Rhodium

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Review Article: 1,4-Benzodiazepines
« Reply #8 on: September 20, 2004, 02:49:00 PM »