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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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	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				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 . 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 .



		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				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}

All 9 posts	End of thread	Top