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Notes on the chemistry and pharmacology of 1-Benzylpiperazine (BzP)
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From: LupusYonderboy
Subject: 1-Benzylpiperazine, Piberaline, Fipexide and related compounds
Date: Tue, 17 Jun 1997 11:21:51 -0700
1-Benzylpiperazine
1-Benzylpiperazine is a CNS stimulant. In doses around 20-100 mg it
produces euphoria, wakefullness, improved vigilance. The ratio of
centeral/peripheral effects is roughly that of d-amphetamine. The
duration of action is 6-8 hours.
Benzylpiperazine, like the amphetamines triggering the release of dopamine
and norepinephine as opposed to blocking their re-uptake as do cocaine,
amfonelic acid, and methylphenidate.
Studies using known amphetamine/methamphetamine addicts showed that 100 mg
was not distinguishable from 7.5 mg of d-amphetamine.
They also noted that lower doses were not detected by the subjects.
Piberaline
Piberaline is 1-benzyl-4-picolonyl-piperazine; the picolonic acid amide of
BZP and is metabolised to BZP. It has been researched as an antidepressant.
1-Piperonylpiperazine
Piperonylpiperazine also referred to as 1-(3,4-methylenedioxy)-benzyl-
piperazine (MDBPZ) shares the same substiutions on the benzene ring as
methylenedioxyamphetamine (MDA). I do not know of any referrence to MDA
like activity. There are animal studies indicating that it blocks the
putative neurotoxic effects of MDMA and possibly the enactogenic effects as
well.
If it has MDA like effects they might not occur in reasonable doses.
BZP is ~1/10 the potency of d-amphetamine. If piperonylpiperazine has a
similar drop in potency that would put the dose in the 1000 mg range. Then
again speculation based on structural relationship to activity is
notoriously unreliable.
Fipexide
Fipexide is a nootropic sold under the brand name Vigilor. Originally
marketed towards the geriatric patient it has become one of the growing
number of drugs used as cognitive enhancers.
Interestingly it is the p-chlorophenylacetamide of piperonylpierazine
(MDBZP) and is converted to MDBZP in vivo. It is availiable from mail
order pharmacies specializing in smart drugs. Anyone with experience with
Fipexide is encouraged to share their knowledge.
Other BenzylPiperazine Derivatives
1-Benzyl-4-diphenylmethylpiperazine exibits cerebral vasodialating
properties, many analogs have been synthesised. The 3,4,5 trimethoxy being
the most potent if I recall. There are phosphonate derivatives that are Ca
channel blockers.
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One might also wish to check out: Sury and Hoffmann (1954) Uber
alkyleniminderivate. Piperidin-derivate mit zentralerregender wirkung I,
Helv. Chim. Acta. 37:2133-2145.
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CAS No's:
[2759-28-6] 1-benzylpiperazine
[72878-35-4] 1-benzylpiperazine HCl
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As a matter of fact I HAVE had experience with this chemical/drug.
I made it myself from benzyl chloride and a mixture of piperazine-6H2O/
piperazine-HCl-2H2O (That I made from livestock wormer!!!). I have and
Organic Syntheses reference around here somewhere.
Frankly, I didn't like it very much. It _was_ a stimulant, but it caused
some jaw clenching and nervous tics (I couldn't stop playing with my
goatee. I mean I REALLY couldn't stop!).
It has what I would call a "serotonin component". I do't think explaining
that term in depth would be in the scope of this group. It's just not
exactly like amphetamines qualittatively. I also can not confirm whether
or not I had formed any dibenzylpiperazine, but the ref for the synth
said that the purity would be high. (That's why the salt system mentioned
is used.) That compound has a pharmacology all it's own. It would be
something of an antihistamine /maybe/.
Something tells me that ring substitution might produce interesting
compounds maybe like MDMA. Putting some sort of small aliphatic
group on the benzyl carbon might be interesting too.
A final note. I'm also not sure of my dosage. I /think/ Iit was a range
of 75-250 mg. 75 producing little effect and 250 feeling yucky.
Anthony
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Here is a quote from a letter from a resercher who is using TFMPP and
BZP HCl in his studies:
"Benzylpiperazine Hydrochloride (BZP HCl) simulates methamphetamine use
in lab animals. It is a strong anorexic. Anorexic capacity is
frequently equated with euphoriant capacity... My observations show
this correlation to be true.
3-Trifluoromethylphenylpiperazine Monohydrochloride (TFMPP), mimics MDMA
in lab animals. A combination of BZP HCl and TFMPP has been observed to
cause activity that is prefered to MDMA in chemical discrimination tests
with lab animals.
A ratio of 2 parts BZP HCl to 1 part TFMPP was used for these chemical
descrimination tests. Larger laboratory primates were given 200 mg. of
BZP HCl mixed with 100 mg. of TFMPP. Observed activity appeared to last
from 6 to 10 hours. There was an increased sociability observed in all
animals given this preparation.
Loss of apetite was observed both in the BZP HCl only group and the BZP
HCL and TFMPP (2:1) group."
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I have read that benzyl piperazine is an active stimulant
similiar in properties to amphetamines in a dosage of 20-100 mg.
I have read this in PiHKAL by our good friend Dr. Shulgin. I
seem to recall his reaction to make "E" entry number 72. Is it
not possible that reacting p-methoxyphenol with fromyl
piperazine as a 40% solution with a 40% solution of formaldehyde
heated on steam bath would yield a substituted benzlpiperazine
just requiring the conversion of the hydroxy group to a methyl
ether and the addition of a bromine in the benzenes fourth
position as well as removal of the formyl group. Sounds good so
far but how to make the methyl ether from the hydroxyl- I tend
to think that a alkali hydroxide and alkyl halide may work but
by products would be high in terms of the quarternary ammonium
halides formation. If there was maybe a way to convert the
quarternary ammonium halide back to a three degree amine.
Another possible route maybe is to use methyl sulfate and
hydroxide or carbonate. Or possibly the diazomethane reaction
but how would a formyl or if removed a two degree amine
react-would it? A layer of ether could hold the substituted
benzylpiperazine and the aqeous layer hold the precursors to the
diazomethane. One last question how would one concentrate the
reactants so that poly piperazinomethylation does not occur in
the other opn ortho position of the phenol? I think much might
be discovered by delving into various analogs of
benzylpiperazines. I would greatly appreciate input from my
fellow experimental innovators of hypothetical chemistry.
Thanks in advance
cornbred
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MDA piperazine derivative
Author: Sub Human
Date: 1996/08/13
Forums: alt.drugs.chemistry
Did anybody catch the comment in Shulgins book about the amphetamine
like properties Benzyl Piperazine posseses? I even think he said
something about the possibility of 3,4 methylenedioxy benzylpiperazine
having MDA like qualities. Well heres a brief skeleton of a synthesis I
worked out for this intriguing molecule.
First off if you can get ahold of piperonal then great, but most people
can't. So we'll start from a more basic building block- isosafrole.
This is oxidized with Na2Cr2O7/H2SO4 as gunther directs in his essential
oils volumes to yield 80% piperonal as the bisulphite complex. The
solid bisulphite complex is boiled with sodium carbonate to give a good
yield of pure piperonal(3,4 methylenedioxy benzaldehyde). This aldehyde
is reacted with formaldehyde and KOH to give a 70% yield of the benzyl
alcohol as illustrated in Org. Syn. Coll. Vol. 2 . The alcohol is then
chlorinated with thionyl chloride to yield 3,4 methylenedioxy
benzylchloride. This is reacted with 2 moles of piperazine (DOES ANYONE
KNOW HOW WATCHED THIS CHEM. IS?) as directed in org syn vol 5 to give a
high yield of 3,4 methylenedioxy benzylpiperazine.
Any comments on this one?
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Subject: 1-Benzylpiperazine HCL
Author: Soma
Date: 1997/07/31
Forums: alt.drugs.chemistry
Has anyone tried this conversion of 1-Benzylpiperazine to 1-
Benzylpiperazine HCL ? Does it work. What is the dosage? Also i've been
told that it should be ingested, not snorted or injected. Is this true?
This is a synth ive seen.
1.) To 35.25 grams of benzyl piperazine add 99% Isopropyl alcohol to
make 200 ml. of solution.
2.) Make a separate solution containing 250 ml of chilled acetone and
35 ml of concentrated Hydrochloric acid added slowly. After making
this 285 ml of solution, add another 115ml of acetone to make 400 ml
of this solution.
3.) Slowly add 200 ml of the acetone/HCl solution to the
benzylpiperazine solution.
4.) Evaporate.
Any comments?
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> assuming a fictional character purchased bzp (as 55 gm of a liquid), what
> would be the best way to partake, could a non-chemist convert this into a
> crystalline form?
This is easy, and can be done by anybody.
Place 20 grams of liquid benzylpiperazine in a 500 ml glass beaker
(no plastic!) and add 100 ml 99% anhydrous isopropylalcohol or methanol,
and give it a good stir. Next add 15 ml of hardware store hydrochloric
acid (muriatic acid) of 30-31% strength, and stir the solution again until
it is thorougly mixed. Now, while stirring, add 250 ml of acetone in 50 ml
portions. Now white benzylpiperazine hydrochloride crystals will form in
the solution. Let the mixture stand in the refrigerator for an hour, break
up any lumps of crystals that may have formed, and filter them off with
a coffee filter and let the crystals completely dry in the air.
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Benzylpiperazine
Author: Anonymous
Date: 1997/05/01
Forums: alt.drugs.chemistry
Benzylpiperazine, N-Benzylpiperazine 1-Benzylpiperazine
CAS no. 2759-28-6
H
N
/ \
| |
\ /
N
|
CH2
|
/ \
| O |
\ /
Appearance colourles or yellow oil. Air sensitive moisture sensitive.
Potential Health Effects:
Eye: Contact with eyes may cause severe irritation, and possible eye burns.
Skin: May cause severe irritation and possible burns.
Ingestion: Not available.
Inhalation: May cause severe irritation of the respiratory tract with sore
throat, coughing, shortness of breath and delayed lung edema.
Causes chemical burns to the respiratory tract.
Chronic: Not available.
This was taken from its MSDS, I don't have van nostrand's Hazardous Properties
of Industrial Materials here that should have more info. Sounds nice and
apetising doesn't it....This is the same stuff that Shulgin talks about in
Pihkal. I'm no pharmacologist, if you want the pharmacology... people you've
got the cas number, one of you students with free stn access can go and do a
search with STN. I guess its somewhat like phenylpiperazine with 5HT1a affinity.
Benzylpiperazine is also probably a powerful antihemintic like its parent,
piperazine, so you might not get off but...
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Here is the information regarding 1-benzylpiperazine also known as
N-benzylpiperazine. The benzylpiperazine currently availiable from CRSB is the
chemical discussed in PHIKAL. It is sold as the free base which is caustic
and unstable. It forms a really pretty dicarbonate on standing in open air.
The dihydrochloride is fine with to off white crystals.
Here is the quote from PIHKAL:
There is a benzyl amine that is a pure stimulant, which has been closely
compared to amphetamine in its action This is benzylpiperazine, a base that is
active in the 20 to 100 milligram range, but which has an acceptability similar
to amphetamine. If this is a valid stimulant, I think that much magic might be
found in and around compounds such as (1) the MDMA analogue, N-(3,4-methylene-
dioxybenzyl)piperazine (or its counterpart N-(3,4-methylenedioxybenzyl)-N'-
methylpiperazine) or (2) the DOM analogue, 2,5-dimethoxy-4-methylbenzylpiperazine.
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MukiBear, Personal BzP notes:
Got my first taste of BzP 'bout two weeks ago - the freebase form.
Started out with 100 mgs, now up to about 200 mgs per dose.
First some questions. One supplier offers BzP freebase liquid, 97%.Well, 3%
what? One would assume H2O or EtOH, just to keep the stuff liquid, but it'd be
nice to know. Also, has anyone tried snorting the carbonate salt (what forms
when you just let it dry out)? Personally, I hate snorting anything and wouldn't
try it, but others have different tastes. Lastly, after a week of daily use, I
developed a mild bladder infection, which cleared up immediately with
antibiotics. Another test subject also noticed some similar irritation. Not to
get too physical, but frequent urination seems to be an effect of the drug, and
I was wondering if anyone else had noticed anything similar...
Okay, time for ratings and reviews.
Mvua (ie, MukiBear) gives straight BzP 4 outta 5 for recreational purposes,
better than Bontril/phendimetrazine/doctor-speed, *way* better than street-
crank, not quite as good as real ice. Other subjects agree. On the Shulgin
psychospiritual scale, though, it's a flat zero, no value at all.
[MukiBear now disagrees - BzP is the best meditation aide this Bear has ever
encountered - sure beats the hell out of green tea]
100 mgs BzP + 1.5 mls 1,4 BDO:
5 outta 5. The G just takes the edge off the speed, and it *rocks* to be on G
and not be at all sleepy. Still zero on Shulgin scale.
150 mgs BzP + several oz EtOH:
I normally hate alcohol, but speed makes me crave drink. Again, 5 outta 5 -
drunk without being sloppy, *very* fun to socialize, etc. Shulgin zero.
50 mgs BzP + 500 mgs DXM +1 mg Xanax:
3 outta 5, recreational, +1 on Shulgin. Mostly just weird and kinda scary.
It's very ODD to have focus on DXM, and not altogether pleasant. Had hoped
for something like DXM + MDA, but no dice.
150 mgs BzP + 500 mgs DXM + 1 mg Xanax + MJ:
Fuckin' rocks! 5/5 recreational, ++ Shulgin. Very interesting and well worth
repeating - must try taking BzP after hitting 2nd or 3rd plateau. Strangely
powerful - I couldn't drive at all (2nd plateau is usually no problem).
150 mgs BzP + 10 mg hydrocodone:
Yeah, I know it's not safe, Belushi-bullshit, but it's fun as hell. Lortab is
a stimulant for confirmed junkies, and this combo made me jump around like a
jackrabbit on cocaine. In deference to my ancestors: yeeeee-haw! 5/5, 0 Shulgin.
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N-BENZYLPIPERAZINE (BZP)
A Benzyl Amine, A CNS Stimulant.
I've received a fair amount of correspondance regarding BZP recently.
The central issues seem to be:
* "Is Shulgin refering to N-Benzylpiperazine?"
* "Is it an amphetamine like CNS stimulant?"
Both are true. BPZ is about one tenth the potency of dextroamphetamine
but in comparable doses subjectively the same.
In the PHIKAL, within the commentary on phenethylamine, Shulgin took the
oppotunity to discuss two related classes compounds.
Benzyl amines- compounds where the benzene ring is connected to the
amine nitrogen by one carbon
Phenyl amines- compounds where the benzene ring is connected to the
amine nitrogen directly.
One benzyl amine he states is an amphetamine like CNS stimulant. His
exact words were
"There is a benzyl amine that is a pure stimulant, which has been
closely compared to amphetamine in its action This is
benzylpiperazine,
a base that is active in the 20 to 100 milligram range, but which
has an
acceptability similar to amphetamine.
Dirk deGroeten pointed out, quite correctly that there is more than one
posible benzylpiperazine stating:
"How can you be sure that Shulgin isn't talking about
2-benzylpiperazine, which in structure is much closer to
amphetamine ?"
I responded that I concluded that Shulgin was indeed refering to the
N-benzylpiperazine. If he were refering to the 2-benzylpiperzine it
would not be a benzylamine. Further when addressing the MDMA analog he
did specify (N-(3,4-methylenedioxy)piperazine). None the less, I had
very little information on benzylpiperazine (BZP) and it sounded
interesting.
The following abstracts concure. I would be fascinated to know if the
3.4 methylenedioxy analog or the 4Me 2,5DiMeO BPZ had CNS activity
related to their phenethylamine/phenisopropylamine counterparts.
Here are a few abstracts I ran across:
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Title: A comparison of the effects of 1-benzylpiperazine and
dexamphetamine on performance tests. Comparison of the effects
of dexamphetamine and 1-benzylpiperazine in former addicts.
Author: Bye C.; Munro Faure A.D.; Peck A.W.; Young P.A.
Publ: EUR.J.CLIN.PHARMACOL., (1973) 6/3 (163-169).
The subjective, behavioural and autonomic effects of dexamphetamine
10 mg, 1 benzylpiperazine 100 mg and lactose dummy were compared in a
group of 18 former amphetamine addicts. All subjects received the three
preparations according to a balanced design under double blind
conditions. 1-Benzylpiperazine and dexamphetamine produced
indistinguishable subjective effects and both were liked. The effects
of both compounds differed significantly from the effects following the
dummy preparation. Increases in pulse rate and both systolic and
diastolic blood pressure were similar following the two active
compounds, but 1 benzylpiperazine produced pupillary dilation whereas
no significant change in pupil size followed dummy or dexamphetamine.
It was concluded that 1 benzylpiperazine is a compound liable to abuse
by an addict population, and that this type of study might be of value
in predicting abuse liability of other new drugs.
------------------------------------------------------------------------
Title: Benzylpiperazine Derivatives. I. Syntheses and Biological
Activities of 1-(2,3,4-Trimethoxy Benzyl)Piperazine Derivatives
Author: Ohtaka H; Miyake M; Kanazawa T; Ito K; Tsukamoto G
Publ: Chem.Pharm.Bull. (35, No. 7, 2274-81, 1987)
A series of 1-(2,3,4-trimethoxy benzyl)piperazine derivatives (3-6) was
prepared and almost all were found to possess stronger activity than
trimetazidine when tested for cerebral vasodilating activity, by
measuring the ratio of the maximum change of blood flow in vertebral
arteries after i.v. administration of the test compound (1 mg/kg) to
that of papaverine (1 mg/kg) in mongrel dogs (11-18 kg). (6 e-j) Were
more active than cinnarizine and papaverine, and (6e) was shown to
exhibit a selective effect on vertebral arteries.
------------------------------------------------------------------------
Title: Synthesis and some CNS activities of new benzofuranylacryloyl-
piperazines.
Publ: Eur.J.Med.Chem. (30, No. 1, 53-59, 1995) 1 Tab. 29
Among a series of novel compounds (cmpds) including 7a-7s (all (E)-4-
(3-(2-benzofuranyl) acryloyl)-1-R-piperazines HCl), 12((E)-4-cinnamoyl-
1-benzylpiperazine HCl and 13 ((E + Z)-4-(3-(3-2H-chromenyl) acryloyl)-
1-benzylpiperazine HCl), only the non-substituted phenyl (7a, i.p.)
showed good antidepressant activity vs. tetrabenazine-induced palpebral
ptosis in mice. The 3,4-methylenedioxy- disubstituted cmpd 7i had
similar anticonvulsant activity vs. maximal electroshock seizures (MES)
to cmpd 7h. Among cmpds substituted at the 5 position of the benzofuran
ring, only the methoxy cmpd 7n was more active than 7h and had best
overall pharmacological activity. The 6-methoxy derivative 7o showed
similar anticonvulsant activity to 7n but was slightly more toxic.
Befuraline, imipramine and carbamazepine were reference drugs.
LupusYonderboy, Doctor of the poison path
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Stimulus properties of antidepressants in the rat.
Source: Psychopharmacology (Berl), 1980 Feb, 67:2, 111-8
Abstract
Various doses of bupropion HCl (Wellbatrin) (5, 10, and 20 mg/kg), a new
phenylaminoketone antidepressant, were employed as cues in a two-lever
operant discrimination from saline control injections in rats on an FR10
schedule of food reinforcement. Subjects reached and maintained a high
level of discrimination in the O vs 20 mg/kg bupropion stimulus condition
but not at the lower doses. In generalization testing, the following
compounds produced dose-related responding on the bupropion lever:
viloxazine, nomifensine, caffeine, d-amphetamine, cocaine, methylphenidate,
and benzylpiperazine. Drugs that failed to show dose-related generalization
included phenethylamine, thyrotropin-releasing hormone, imipramine,
nortriptyline, amitriptyline, desipramine, mianserin, chlordiazepoxide,
diazepam, scopolamine, phenobarbital, and morphine. With the important
exception of viloxazine, the generalization profile of bupropion seems to
reflect its previously reported locomotor stimulant effects in the rat
rather than its antidepressant activity and suggests that species
differences exist between man and rat with regard to the pharmacologic
activity of this new antidepressant.
- - - - -
Studies on the biochemical mode of action of EGYT-475, a new antidepressant.
Source: Pol J Pharmacol Pharm, 1987 Mar-Apr, 39:2, 203-11
Abstract
We studied the mode of action of N-benzyl-piperazine-picolinylfumarate
(EGYT-475) and of its metabolite N-benzyl-piperazine (EGYT-2760) in CFY
rats. It was found that EGYT-475 had no uptake-inhibitory effect but
EGYT-2760 inhibited the high-affinity uptake of 3H-noradrenaline,
3H-dopamine and especially that of 3H-serotonin both in vitro and ex
vivo. Neither of the two compounds changed the serotonin turnover. Only
EGYT-2760 evoked hyperthermia in rats at a high ambient temperature
(28 degrees C). This effect was abolished by cyproheptadine but not by
amitriptyline. EGYT-2760 antagonized serotonin-induced contractions of
the stomach fundus but it was inactive in inhibiting the serotonin-
induced platelet aggregation. Our results suggest that EGYT-2760, an
active metabolite of EGYT-475, has a central serotoninomimetic action
which involves 5-HT uptake-inhibition and 5-HT1 receptor agonistic effect.
- - - - -
Pharmacokinetic aspects of the mode of action of EGYT-475, a new antidepressant.
Source: Pol J Pharmacol Pharm, 1987 Mar-Apr, 39:2, 107-12
Abstract
EGYT-475 (N-benzyl-piperazine-picolinyl fumarate; Trelibet) metabolism was
compared in rats, dogs and man. In the rat 7 urinary metabolites of EGYT-475
were found, and 4 were identified as: N-picolinyl-piperazine (EGYT-1354)
(30%), picolinic acid (28.5%), hippuric acid (53%) and N-benzylpiperazine
(EGYPT-2760) (3.7%). The results show that debenzylation is the main route
of EGYT-475 metabolism in the rat. By this route EGYT-2760, the active
EGYT-475 metabolite, is further metabolized. In the dog the main metabolic
pathway is hydrolysis, and because of that the formed EGYT-2760 is not
metabolized further and its urinary content exceeds 50%. In man, similarly
as in the rat, debenzylation is the preferred route of EGYT-475 metabolism.
These results explain much higher toxicity of EGYT-475 in dogs than in rats
and man.
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Title
Effects of benzylpiperazine derivatives on the neurotoxicity of
3,4-methylenedioxymethamphetamine in rat brain.
Author
Hashimoto K; Maeda H; Goromaru T
Source
Brain Res, 1992 Sep 11, 590:1-2, 341-4
Abstract
The neurotoxicity of 3,4-methylenedioxymethamphetamine (MDMA) in rat
brain was attenuated significantly by coadministration of several benzyl-
piperazines (p-nitrobenzylpiperazine, p-chlorobenzylpiperazine and
1-piperonylpiperazine), which were weak inhibitors for [3H]6-nitro-
quipazine binding to the 5-hydroxytryptamine (5-HT) transporter in rat
brain. These results suggest that these benzylpiperazines may inhibit the
MDMA-induced neurotoxicity by a novel neuropharmacological effect other
than 5-HT uptake inhibition.
================================================================================
Title
Effects of benzylpiperazine derivatives on the acute effects of
3,4-methylenedioxymethamphetamine in rat brain.
Author
Hashimoto K
Source
Neurosci Lett, 1993 Apr 2, 152:1-2, 17-20
Abstract
The reduction of 5-hydroxytryptamine (5-HT) in rat brain 3 h after
administration of 3,4-methylenedioxymethamphetamine (MDMA) was attenuated
significantly by coadministration of benzylpiperazine derivatives
(p-nitrobenzylpiperazine, p-chlorobenzylpiperazine and 1-piperonyl-
piperazine), which were weak inhibitors of [3H]5-HT uptake into rat brain
synaptosomes. However, the coadministration of desipramine and imipramine
which were more potent 5-HT uptake inhibitors than these benzyl-
piperazines, did not attenuate the reduction of 5-HT by MDMA. These
results suggest that these benzylpiperazines might inhibit the acute
effects of MDMA by a novel neuropharmacological effect other than 5-HT
uptake inhibition.
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Title
Comparison of serotonin agonistic and antagonistic activities of a new
antidepressant agent Trelibet (EGYT-475) and its metabolite EGYT-2760 on
isolated rat fundus.
Author
Malomvölgyi B; Tóthfalusi L; Tekes K; Magyar K
Source
Acta Physiol Hung, 1991, 78:3, 201-9
Abstract
The effects of Trelibet (EGYT-475, N-benzyl-piperazine-picolinyl-fumarate)
and its active metabolite (EGYT-2760, N-benzyl-piperazine) on the
serotoninergic responses of rat stomach fundus were investigated and
compared with those of MCPP (m-chlorophenyl-piperazine) which is the
common metabolite of the arylpiperazine antidepressants Trazodone and
Etoperidone. The contraction inhibitory potencies of the agents were
determined on the equipotent contractions (EC50) to serotonin (5-HT) and
prostaglandin F2 alpha (PGF2 alpha). Isotonic contractile responses to
5-HT were not affected by EGYT-475, however, both EGYT-2760 and MCPP
produced concentration related and reversible inhibition of the
serotoninergic responses. The IC50 values for EGYT-2760 and MCPP were
40.5 +/- 7.5 mumol/l and 125 +/- 35 nmol/l, respectively. The inhibition
was selective for the serotoninergic responses, as the equipotent
responses to PGF2 alpha were not affected. EGYT-2760 and MCPP displayed
not only 5-HT antagonistic, but also partial agonistic activities on the
rat fundus preparation. Maximum contractile response of the fundus
preparation to MCPP was approximately 25%, to EGYT-2760 was 10% of the
maximum response to 5-HT.
================================================================================
From: Tom Kasper
Subject: Methamphetamine and Benzylpiperazine; same mechanism of action
Date: Fri, 03 Oct 1997 09:51:51 -0700
While chemically dissimilar benzylpiperazine and methamphetamine almost
indistinguishable subjective effects in humans and as the following
abstract suggests seem to do so through the same mechanism of action.
Title: Circling behavior induced by dopamine releasers and/or uptake
inhibitors during degeneration of the nigrostriatal pathway
Author: Oberlander, Claude; Euvrard, Catherine; Dumont, Claude;
Boissier, Jacques R.
Pub: Eur. J. Pharmacol. (1979), 60(2-3), 163-70
Abstract:
A no. of compds. which induce ipsilateral circling behavior in rats with
chronic unilateral 6-hydroxydopamine (6-OHDA) destruction of the
nigrostriatal dopamine (DA) [51-61-6] pathway through their postulated
DA-releasing and/or uptake-inhibiting properties, were tested 24 h after a
6-OHDA lesion. Under these conditions, in contrast to chronically lesioned
animals, d [51-63-8] or l-amphetamine sulfate [51-62-7],
d-methamphetamine-HCl [51-57-0], and benzylpiperazine-HCl [72878-35-4]
induced contralateral turns whereas methylphenidate-HCl
[298-59-9],pipradrol-HCl [71-78-3], dl-p-chloroamphetamine-HCl [3706-38-5],
mazindol [22232-71-9], HR370 [73068-25-4], nomifensine maleate
[32795-47-4], benztropine mesylate [132-17-2] still induced ipsilateral
turns. The monoamine oxidase inhibitor pargyline-HCl [306-07-0] was
inactive and the DA receptor agonist apomorphine-HCl [314-19-2] induced a
mild contralateral circling response at high doses only. The contralateral
circling response to d-amphetamine was hardly antagonized by a high dose of
dl-.alpha.-Me p-tyrosine Me ester(AMT), and was increased by reserpine.
Striatal DA levels were increased in the lesioned side and restored to
normal values after d-amphetamine, in contrast to methylphenidate.
Ipsilateral turns recorded with chronically lesioned rats were strongly
decreased by AMT except in the case of p-chloroamphetamine, methylphenidate
and pipradrol. The response of reserpinized rats was decreased except with
d-amphetamine and its N-Me deriv. Thus, drugs inducing contralateral turns
during degeneration of the nigrostriatal DA pathway predominantly release
newly-synthesized DA independently of nerve impulse flow, whereas
ipsilateral turns are either triggered by inhibiting of DA uptake or by the
release of the reserpine-sensitive pool of DA, both on the intact side.
This last effect may require a normal nerve impulse flow. This method thus
provides the first direct behavioral evidence of differences in the mode of
action of drugs interfering presynaptically with DA.
================================================================================
MATERIAL SAFETY DATA SHEET
1-Benzylpiperazine, 97+%
32841
**** SECTION 1 - CHEMICAL PRODUCT AND COMPANY IDENTIFICATION ****
MSDS Name: 1-Benzylpiperazine, 97+%
Company Identification: Acros Organics N.V.
One Reagent Lane
Fairlawn, NJ 07410
For information in North America, call: 800-ACROS-01
For emergencies in the US, call CHEMTREC: 800-424-9300
**** SECTION 2 - COMPOSITION, INFORMATION ON INGREDIENTS ****
+----------------+--------------------------------------+----------+-----------+
| CAS# | Chemical Name | % | EINECS# |
|----------------|--------------------------------------|----------|-----------|
| 2759-28-6 |1-Benzylpiperazine, 97% | | 220-423-6 |
+----------------+--------------------------------------+----------+-----------+
Hazard Symbols: C
Risk Phrases: 34
**** SECTION 3 - HAZARDS IDENTIFICATION ****
EMERGENCY OVERVIEW
Appearance: clear colorless to faint yellow.
Light sensitive. Air sensitive. Moisture sensitive.
Target Organs: None.
Potential Health Effects
Eye:
Contact with eyes may cause severe irritation, and possible eye
burns.
Skin:
May cause severe irritation and possible burns.
Ingestion:
Not available.
Inhalation:
May cause severe irritation of the respiratory tract with sore
throat, coughing, shortness of breath and delayed lung edema. Causes
chemical burns to the respiratory tract.
Chronic:
Not available.
**** SECTION 4 - FIRST AID MEASURES ****
Eyes:
Immediately flush eyes with plenty of water for at least 15 minutes,
occasionally lifting the upper and lower lids.
Skin:
Flush skin with plenty of soap and water for at least 15 minutes
while removing contaminated clothing and shoes.
Ingestion:
Do NOT induce vomiting. Allow the victim to rinse his mouth and then
to drink 2-4 cupfuls of water, and seek medical advice.
Inhalation:
Remove from exposure to fresh air immediately.
Notes to Physician:
Treat symptomatically and supportively.
**** SECTION 5 - FIRE FIGHTING MEASURES ****
General Information:
As in any fire, wear a self-contained breathing apparatus in
pressure-demand, MSHA/NIOSH (approved or equivalent), and full
protective gear.
Extinguishing Media:
Not available.
Autoignition Temperature: Not available.
Flash Point: > 112 deg C (> 233.60 deg F)
NFPA Rating: Not published.
Explosion Limits, Lower: Not available.
Upper: Not available.
**** SECTION 6 - ACCIDENTAL RELEASE MEASURES ****
General Information: Use proper personal protective equipment as indicated
in Section 8.
Spills/Leaks:
Absorb spill with inert material, (e.g., dry sand or earth), then
place into a chemical waste container.
**** SECTION 7 - HANDLING and STORAGE ****
Handling:
Not available.
Storage:
Corrosives area.
**** SECTION 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION ****
Engineering Controls:
Use adequate general or local exhaust ventilation to keep airborne
concentrations below the permissible exposure limits.
Exposure Limits
+--------------------+-------------------+-------------------+-----------------+
| Chemical Name | ACGIH | NIOSH |OSHA - Final PELs|
|--------------------|-------------------|-------------------|-----------------|
| 1-Benzylpiperazine,|none listed |none listed |none listed |
| 97% | | | |
+--------------------+-------------------+-------------------+-----------------+
OSHA Vacated PELs:
1-Benzylpiperazine, 97%:
No OSHA Vacated PELs are listed for this chemical.
Personal Protective Equipment
Eyes:
Wear safety glasses and chemical goggles if splashing
is possible.
Skin:
Wear appropriate protective gloves and clothing to
prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize
contact with skin.
Respirators:
Wear a NIOSH/MSHA or European Standard EN 149
approved full-facepiece airline respirator in the
positive pressure mode with emergency escape
provisions.
**** SECTION 9 - PHYSICAL AND CHEMICAL PROPERTIES ****
Physical State: Not available.
Appearance: clear colorless to faint yellow
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Vapor Density: Not available.
Evaporation Rate: Not available.
Viscosity: Not available.
Boiling Point: @ 760.00mm Hg
Freezing/Melting Point: 0 deg C
Decomposition Temperature: Not available.
Solubility: Not available.
Specific Gravity/Density: 1.0140g/cm3
Molecular Formula: C11H16N2
Molecular Weight: 176.26
**** SECTION 10 - STABILITY AND REACTIVITY ****
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Not available.
Incompatibilities with Other Materials:
Strong oxidizing agents - light - air and moisture - strong acids.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, nitrogen.
Hazardous Polymerization: Has not been reported.
**** SECTION 11 - TOXICOLOGICAL INFORMATION ****
RTECS#:
CAS# 2759-28-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-Benzylpiperazine, 97% -
Not listed by ACGIH, IARC, NIOSH, NTP, or OSHA.
Epidemiology:
No data available.
Teratogenicity:
No data available.
Reproductive Effects:
No data available.
Neurotoxicity:
No data available.
Mutagenicity:
No data available.
Other Studies:
No data available.
**** SECTION 12 - ECOLOGICAL INFORMATION ****
Ecotoxicity:
Not available.
**** SECTION 13 - DISPOSAL CONSIDERATIONS ****
Dispose of in a manner consistent with federal, state, and local regulations.
RCRA D-Series Maximum Concentration of Contaminants:
None listed.
RCRA D-Series Chronic Toxicity Reference Levels: None
listed.
RCRA F-Series: None listed.
RCRA P-Series: None listed.
RCRA U-Series: None listed.
**** SECTION 14 - TRANSPORT INFORMATION ****
US DOT
Shipping Name: CORROSIVE LIQUID, BASIC, ORGANIC, N.O.S.
(1-BENZYLPIPERAZINE)
Hazard Class: 8
UN Number: UN3267
Packing Group: II
IMO
Shipping Name: CORROSIVE LIQUID, BASIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3267
Packing Group: II
IATA
Shipping Name: CORROSIVE LIQUID, BASIC, ORGANIC, N.O.S.*
Hazard Class: 8
UN Number: 3267
Packing Group: II
RID/ADR
Shipping Name: CORROSIVE LIQUID, BASIC, ORGANIC, N.O.S.
Dangerous Goods Code: 8(56B)
UN Number: 3267
Canadian TDG
No information available.
**** SECTION 15 - REGULATORY INFORMATION ****
US FEDERAL
TSCA
CAS# 2759-28-6 is listed on the TSCA inventory.
Health & Safety Reporting List
None of the chemicals are on the Health & Safety Reporting List.
Chemical Test Rules
None of the chemicals in this product are under a Chemical Test Rule.
Section 12b
None of the chemicals are listed under TSCA Section 12b.
TSCA Significant New Use Rule
None of the chemicals in this material have a SNUR under TSCA.
SARA
Section 302 (RQ)
None of the chemicals in this material have an RQ.
Section 302 (TPQ)
None of the chemicals in this product have a TPQ.
Section 313
No chemicals are reportable under Section 313.
Clean Air Act:
This material does not contain any hazardous air pollutants.
This material does not contain any Class 1 Ozone depletors.
This material does not contain any Class 2 Ozone depletors.
Clean Water Act:
None of the chemicals in this product are listed as Hazardous
Substances under the CWA.
None of the chemicals in this product are listed as Priority
Pollutants under the CWA.
None of the chemicals in this product are listed as Toxic Pollutants
under the CWA.
OSHA:
None of the chemicals in this product are considered highly hazardous
by OSHA.
STATE
1-Benzylpiperazine, 97% is not present on state lists from CA, PA,
MN, MA, FL, or NJ.
California No Significant Risk Level:
None of the chemicals in this product are listed.
European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 34 Causes burns.
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 2759-28-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
WHMIS: Not available.
CAS# 2759-28-6 is not listed on Canada's Ingredient Disclosure List.
Exposure Limits
**** SECTION 16 - ADDITIONAL INFORMATION ****
MSDS Creation Date: 3/01/1994 Revision #2 Date: 9/02/1997
The information above is believed to be accurate and represents the best
information currently available to us. However, we make no warranty of
merchantability or any other warranty, express or implied, with respect to
such information, and we assume no liability resulting from its use. Users
should make their own investigations to determine the suitability of the
information for their particular purposes. In no way shall Fisher be liable
for any claims, losses, or damages of any third party or for lost profits
or any special, indirect, incidental, consequential or exemplary
damages, howsoever arising, even if Fisher has been advised of
the possibility of such damages.
================================================================================
CAS # [2759-28-6]
FW 176.26
Molecular formula C11H16N2
Water determination <=0.5% (K.F.)
d 1.0140
Refractive index (sodium D) 1.5467
Fp >112°
Hazard symbol C
Risk/safety phrases R 34 S 24/25 UN 3267 DOT 8
Properties LIGHT SENSITIVE
AIR SENSITIVE
EINECS 220-423-6
================================================================================
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