Newsgroups: alt.drugs
From: yshan@bcarh697.bnr.ca (Yogi Shan)
Subject: Re: Research information
Message-ID: <1994Jun8.211107.26019@bcarh54a.bnr.ca>
Date: Wed, 8 Jun 1994 21:11:07 GMT

Lamont Granquist (lamont@hyperreal.com) wrote:
: synner@cyberspace.com (Ben Lincoln) writes:
: >Hello. I'm doing a research project on various psychedelics and I was 
: >wondering if anyone here has information on any of the following substances:
: >	BZ, STP, and MK-801
: BZ comes up frequently on alt.drugs, but all i ever bother to remember is
: that its nasty...

BZ = 3-quinuclidinyl benzillate

Developed in the '50s; stockpiled as a non-lethal
chemical warfare agent by U.S. DoD until the early '80s.

Related to the JB-series (eg. Ditran) of benzillate
ester hallucinogens.

Synthesis is simple, if I recall correctly:  esterify
3-quinuclidinol with benzillic acid.  I believe it
made a very brief appearance on the streets as either
"TWA" or "DMZ" during the '60s, according to published
sources.  I believe the effects are of the deliriant-
type, similar to datura/belladonna/atropine.

[ correction added 5/97: "Correct statement is that BZ has never been
  available.  TWA & DMZ were benactyzine & Ditran, but I'm not sure which
  is which." -- yshan@nortel.ca ]

Further info, including tox data may be found in 
the "Merck Index", available in the Reference section
of any decent library.


Yogi

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Newsgroups: alt.drugs
Message-ID: <5QQYd2N3zI@bion101.bionic.zer.de>
From: M.LIEBERMANN@BIONIC.zer.de (Martin Liebermann)
Subject: Re: Research information
Date: Tue, 07 Jun 1994 21:16:00 +0200

[text deleted -cak]

About BZ i found the following news in my archive:
---------------------snip------------------------------------------------------

Nachricht von    : bwhite@oucsace.cs.ohiou.edu (William E. White )
Betrifft         : Re: Your worst nightmare
Erstellungsdatum : 06.02.1994 14:19:29 W+0:00

In article <lonewolfCKqK9q.B9u@netcom.com>,
Joseph E. Gladstone <lonewolf@netcom.com> wrote:
>: Sounds like BZ to me. I guess it's closely related to nerve gas. The feature
>: film "Jacob's Ladder" portrayed BZ experiments in Vietnam during the war.
>: Jody

>No way - BZ lasts for quite a while depending on doseage, 8 - 72 hours.
>Cholinergics produce wierd effects, but not predictably nightmarish.

Actually, BZ (quinuclidinol benzilate, or QNB) is an anticholinergic,
acting specifically on muscarinic receptors.  It is extremely potent (and
is, in fact, used in research for its antimuscarinic properties).  It
also seems to have a greater LD50/ED50 ratio than other antimuscarinics
(such as atropine, scopolamine, etc).  But I wouldn't try it, it's still
not particularly safe.  Incidentally, it has been reported to tend to
induce nightmarish hallucinations/delusions (I could never find out why).
In any case, I can imagine that in a combat situation, one could easily
find onesself in a bad trip.


(Bad ASCII drawing to follow):


ASCII drawing of QNB (sorry, not too great.  The two rings on the top
and bottom are phenyl groups).


                          / \\
            N            ||  |
          / \ \      O    \ //
         |   | |     ||    |
         |   | |__O--C-----C--O--H
          \ / /            |
                          / \\
                         ||  |
                          \ //




--
|  Bill White   +1-614-594-3434     | bwhite@oucsace.cs.ohiou.edu             |
|  31 Curran Dr., Athens OH  45701  | bwhite@bigbird.cs.ohiou.edu (alternate) |
|  SCA: Erasmus Marwick, Dernehealde Pursuivant, Dernehealde, Middle Kingdom  |

---------------snap-----------------------------------------------------------


MK-801 I've never heard of.

Greetings

Martin Liebermann

M.Liebermann@bionic.zer.de  * PGP-key available *   fon/fax +49 +521 446729
## CrossPoint v3.02 R ##

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Subject: Re: Research information
Newsgroups: alt.drugs
Date: Tue, 7 Jun 94 18:52:05 EDT

BZ is the benzoicc acid ester of 3-Quinuclidinol.  I believe it was
explored as a chemical warfare incapicitating agent by the CIA.
I know Dr. James Moore who used to be a prof at the U of DE and 
made compounds for the CIA.  He tells some amazing tales.

Case in point:  He made BZ for the CIA and got some on his
hands.  He felt very disoriented.  "I felt like the whole world turned 
sideways on me." This effect lasted for days and so he asked the  big 
boys at the CIA how to get back.  They told him to take some THA 
(tetrahydroacridine) that is now used as an experimental Alzheimers 
treatment.   He claims it straightened him right out.

MK-801 is a sigma opiate receptor agonist (I think) not sure about that one.

Thanks.

--keith
 

=============================================================================

Os, this is terrible compound - long-lasting atropine-like 
hallucinations. Don't do it at home :)) Antidote - tetrahydroacridine.

Synth. - Sternbach, Kaiser, JACS, 74, 2215 (1952) - 
from 3-quinuclidinol (synth. by Sternbach & Kaiser 
from methyl isonicotinate and ehyl bromoacetate -> 
cyclisation this quat. salt with metal potassium - 
sorry, lost this reference...)
and chlorodiphenylacetylchloride (synth. - JACS, 
v.65, 769 (1943))

another QNB-like compd - 

N-ethyl-3-piperidol benzilate, ED near 5 mg on 70 
kg man, duration 5-6 hours)

Ditran aka N-ethyl-3-piperidol phenyl-cyclopentyl-glycolate,
ED 5-15 mg, duration 8-12 hours. 

=============================================================================

Synthesis is very simple.  This is from Chemical Abstracts, 1959, vol 53,
#1385h, under the heading "Esters of diaryl hydroxyacetic acids."  It
references US Patent # 2,843,593.

"Thus, 15 grams anhydrous methyl benzilate in 50 cc dry toluene is added
with stirring to 1.2 gram of sodium metal dispersed in 50 cc toluene, the
mixture kept below 30 degrees (C) by external cooling during hydrogen
evolution.  (1 hour).  Whereupon 5.2 grams anhydrous 3-quinuclidinol in
toluene is added, the mixture refluxed 30 minutes (turns reddish), cooled
to -20 degrees C, (turns pale yellow) extracted 3 times with cold 1-normal
HCl, made alkaline with 35 cc 15% NaOH, extracted 3 times with chloroform,
dried over sodium sulfate, evaporated till crystallization begins, 50 cc of
acetone added, allowed to stand 24 hours in a refrigerator (not further
defined), and the precipitate filtered off and washed with acetone to give
84.2% benzilic acid ester of 3 quinuclidinol, melting point 160-161.  "

Also:

Journal of the American Chemical Society, May 5, 1952, page 2215-2219+ 

Also, from the Merck Index, a reference to a WHO (World Health
Organization) publication, under heading 3-Quinuclidinol.      "Health
Aspects of Chemical and Biological Weapons (WHO, Geneva, 1970, pp 49-51)

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