================================================================================ Notes on the chemistry and pharmacology of 1-Benzylpiperazine (BzP) ================================================================================ 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. ================================================================================ 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. ================================================================================ CAS No's: [2759-28-6] 1-benzylpiperazine [72878-35-4] 1-benzylpiperazine HCl ================================================================================ 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 ================================================================================ 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." ================================================================================ 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 ================================================================================ 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? ================================================================================ 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? ================================================================================ > 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. ================================================================================ 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... ================================================================================ 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. ================================================================================ 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. ================================================================================ 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: ------------------------------------------------------------------------ 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 ================================================================================ 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. ================================================================================ 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. ================================================================================ 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 ================================================================================
Alexander Shulgin -- Memorial Gathering
August 2nd, 1pm-6pm, Berkeley CA
Join us at a memorial service to honor the life and work of Dr. Alexander T. "Sasha" Shulgin (1925-2014) on August 2nd at the Berkeley Community Theater. A potluck reception will follow the service.
For details (and to RSVP), see: Shulgin Memorial at Eventbrite
For details (and to RSVP), see: Shulgin Memorial at Eventbrite