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Methylenedioxybenzylpiperazine: Difference between revisions

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{{Short description|Chemical compound}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
⚫ | verifiedrevid = 447764702
| Watchedfields = changed
⚫ | IUPAC_name = 1-(benzodioxol-5-ylmethyl)piperazine
⚫ | verifiedrevid = 449584568
⚫ | IUPAC_name = 1-(Benzodioxol-5-ylmethyl)piperazine
| image = MDBZP.svg | image = MDBZP.svg
| width = 160 | width = 160
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<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename =
| routes_of_administration = | routes_of_administration =
| legal_DE = NpSG


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 32231-06-4 | CAS_number = 32231-06-4
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 512G6R381X
| ATC_prefix = none | ATC_prefix = none
| ATC_suffix = | ATC_suffix =
| PubChem = 94426 | PubChem = 94426
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 85214
| synonyms = MDBZP; MDBP; Piperonylpiperazine; ''N''-Piperonylpiperazine


<!--Chemical data--> <!--Chemical data-->
| C=12 | H=16 | N=2 | O=2 | C=12 | H=16 | N=2 | O=2
| smiles = c1cc2c(cc1CN3CCNCC3)OCO2
| molecular_weight = 220.268 g/mol
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C12H16N2O2/c1-2-11-12(16-9-15-11)7-10(1)8-14-5-3-13-4-6-14/h1-2,7,13H,3-6,8-9H2
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = NBOOZXVYXHATOW-UHFFFAOYSA-N
}} }}


'''1-(3,4-Methylenedioxybenzyl)piperazine''' ('''MDBZP'''; '''Piperonylpiperazine''') is a ] of the ] ] related to ] (BZP). In the book ] it is speculated that MDBZP might have effects similar to the drug ] (MDMA; "]") because of the presence of the 3,4-methylenedioxy group on the benzene ring; however, once the compound was tested in humans this theory was shown to be incorrect. '''1-(3,4-Methylenedioxybenzyl)piperazine''' ('''MDBZP''', '''piperonylpiperazine''') is a ] of the ] ] related to ] (BZP). MDBZP has been sold as a ]<ref>{{cite journal | vauthors = Maurer HH, Kraemer T, Springer D, Staack RF | title = Chemistry, pharmacology, toxicology, and hepatic metabolism of designer drugs of the amphetamine (ecstasy), piperazine, and pyrrolidinophenone types: a synopsis | journal = Therapeutic Drug Monitoring | volume = 26 | issue = 2 | pages = 127–31 | date = April 2004 | pmid = 15228152 | doi = 10.1097/00007691-200404000-00007 | s2cid = 9255084 }}</ref> and has even been found as an ingredient in street ] pills.{{cn|date=January 2016}}

MDBZP has been sold as a "]" with supposed recreational properties, and has even been found as an ingredient in street "]" pills. However, MDBZP is only a very mild stimulant, and does not produce ], empathogenic or ] effects. The prominent side effects produced by MDBZP are ], ] and ], but at high doses it has been known to cause ]. MDBZP thus has all of the negative side effects of other piperazine derivatives, but without any of the positive effects that might make these drugs desirable to consumers.{{Citation needed|date=August 2010}}


== See also == == See also ==
* ] (MDMA)
* ] (BZP)
* ]
* ] (MBZP)
* ] (DBZP)
* ] (mCPP)
* ] (TFMPP)
* ] (2C-B-BZP)
* ] (pFPP)
* ] (MeOPP)
* ]


== References == == References ==
⚫ {{Reflist}}
{{Unreferenced|date=December 2007}}

⚫ {{Reflist|2}}
==External links==
* {{cite web | url =https://www.who.int/medicines/areas/quality_safety/5.3eMDBZPpre-review.pdf | title =1-(3-4-methylendioxybenzyl)piperazine (MDBZP) Pre-Review Report | author = Expert Committee on Drug Dependence | date = 8 June 2012 | publisher = World Health Organization}}


{{Stimulants}} {{Stimulants}}
{{Monoamine releasing agents}}
{{Adrenergics}}
{{Dopaminergics}}
{{Serotonergics}}
{{Piperazines}} {{Piperazines}}


⚫ ]
] ]
⚫ ]
]




Latest revision as of 06:05, 11 December 2024

Chemical compound Pharmaceutical compound
Methylenedioxybenzylpiperazine
Clinical data
Other namesMDBZP; MDBP; Piperonylpiperazine; N-Piperonylpiperazine
ATC code
  • none
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
Identifiers
IUPAC name
  • 1-(Benzodioxol-5-ylmethyl)piperazine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.046.319 Edit this at Wikidata
Chemical and physical data
FormulaC12H16N2O2
Molar mass220.272 g·mol
3D model (JSmol)
SMILES
  • c1cc2c(cc1CN3CCNCC3)OCO2
InChI
  • InChI=1S/C12H16N2O2/c1-2-11-12(16-9-15-11)7-10(1)8-14-5-3-13-4-6-14/h1-2,7,13H,3-6,8-9H2
  • Key:NBOOZXVYXHATOW-UHFFFAOYSA-N
  (what is this?)  (verify)

1-(3,4-Methylenedioxybenzyl)piperazine (MDBZP, piperonylpiperazine) is a chemical compound of the piperazine chemical class related to benzylpiperazine (BZP). MDBZP has been sold as a designer drug and has even been found as an ingredient in street Ecstasy pills.

See also

References

  1. Maurer HH, Kraemer T, Springer D, Staack RF (April 2004). "Chemistry, pharmacology, toxicology, and hepatic metabolism of designer drugs of the amphetamine (ecstasy), piperazine, and pyrrolidinophenone types: a synopsis". Therapeutic Drug Monitoring. 26 (2): 127–31. doi:10.1097/00007691-200404000-00007. PMID 15228152. S2CID 9255084.

External links

Stimulants
Adamantanes
Adenosine antagonists
Alkylamines
Ampakines
Arylcyclohexylamines
Benzazepines
Cathinones
Cholinergics
Convulsants
Eugeroics
Oxazolines
Phenethylamines
Phenylmorpholines
Piperazines
Piperidines
Pyrrolidines
Racetams
Tropanes
Tryptamines
Others
ATC code: N06B
Monoamine releasing agents
DRAsTooltip Dopamine releasing agents
NRAsTooltip Norepinephrine releasing agents
SRAsTooltip Serotonin releasing agents
Others
See also: Receptor/signaling modulators • Monoamine reuptake inhibitors • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins
Piperazines
Simple piperazines
(no additional rings)
Phenylpiperazines
Benzylpiperazines
Diphenylalkylpiperazines
(benzhydrylalkylpiperazines)
Pyrimidinylpiperazines
Pyridinylpiperazines
Benzo(iso)thiazolylpiperazines
Tricyclics
(piperazine attached via side chain)
Others/Uncategorized


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