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←Created page with '{{Drugbox | IUPAC_name = 2-(4-iodo-2,5-dimethoxyphenyl)-''N''-[(3,4-methylenedioxyphenyl)methyl]ethanamine | image = NB34MD-2CI_structure.png | width = 220 <!--...'
 
recategorized from Iodoarenes to Iodobenzene derivatives
 
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{{Short description|Derivative of the phenethylamine hallucinogen 2C-I}}
{{Drugbox
{{Drugbox
| IUPAC_name = 2-(4-iodo-2,5-dimethoxyphenyl)-''N''-[(3,4-methylenedioxyphenyl)methyl]ethanamine
| IUPAC_name = ''N''-[(2''H''-1,3-Benzodioxol-5-yl)methyl]-2-(4-iodo-2,5-dimethoxyphenyl)ethan-1-amine
| image = NB34MD-2CI_structure.png
| image = 25I-NB34MD.svg
| width = 220


<!--Clinical data-->
<!--Clinical data-->
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| pregnancy_category =
| pregnancy_category =
| routes_of_administration =
| routes_of_administration =
| legal_UK = Class A


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


<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number =
| CAS_number = 1391497-81-6
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = R7X848UW5A
| CAS_supplemental =
| CAS_supplemental =
| ATC_prefix = none
| ATC_prefix = none
| PubChem =
| PubChem =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID =
| ChemSpiderID = 58191429


<!--Chemical data-->
<!--Chemical data-->
| C=18 | H=20 | I=1 | N=1 | O=4
| C=18 | H=20 | I=1 | N=1 | O=4
| smiles = O1C2=C(OC1)C=C(C=C2)CNCCC3=C(C=C(C(=C3)OC)I)OC
| molecular_weight = 441.259 g/mol
| smiles = c3cc2OCOc2cc3CNCCc1cc(OC)c(I)cc1OC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C18H20INO4/c1-21-16-9-14(19)17(22-2)8-13(16)5-6-20-10-12-3-4-15-18(7-12)24-11-23-15/h3-4,7-9,20H,5-6,10-11H2,1-2H3
| StdInChI =
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey =
| StdInChIKey = FWEBGKDUEZRMRQ-UHFFFAOYSA-N
}}
}}


'''25I-NB34MD''' ('''NB34MD-2C-I''') is a derivative of the [[phenethylamine]] [[Psychedelic drug|hallucinogen]] [[2C-I]], which acts as a highly [[potency (pharmacology)|potent]] [[partial agonist]] for the [[human]] [[5-HT2A receptor|5-HT<sub>2A</sub>]] [[Receptor (biochemistry)|receptor]]. It has a binding affinity of 0.67nM at the human 5-HT<sub>2A</sub> receptor, maing it several times weaker than its positional isomer [[25I-NBMD]] and a similar potency to [[25I-NBF]].<ref>{{cite journal | last1 = Braden | first1 = MR | last2 = Parrish | first2 = JC | last3 = Naylor | first3 = JC | last4 = Nichols | first4 = DE | title = Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists. | journal = Molecular Pharmacology | volume = 70 | issue = 6 | pages = 1956–64 | year = 2006 | pmid = 17000863 | doi = 10.1124/mol.106.028720 }}</ref><ref>[http://proquest.umi.com/pqdlink?Ver=1&Exp=01-23-2014&FMT=7&DID=1417800971&RQT=309&attempt=1&cfc=1 Michael Robert Braden PhD. Towards a biophysical understanding of hallucinogen action. Purdue University 2007.]</ref>
'''25I-NB34MD''' ('''NB34MD-2C-I''') is a derivative of the [[phenethylamine]] [[Psychedelic drug|hallucinogen]] [[2C-I]], which acts as a [[potency (pharmacology)|potent]] [[partial agonist]] for the [[human]] [[5-HT2A receptor|5-HT<sub>2A</sub>]] [[Receptor (biochemistry)|receptor]], and presumably has similar properties to 2C-I.<ref>{{cite journal | vauthors = Uchiyama N, Kikura-Hanajiri R, Hakamatsuka T | s2cid=20296244 | title=A phenethylamine derivative 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(3,4-methylenedioxyphenyl)methyl]ethanamine (25I-NB34MD) and a piperazine derivative 1-(3,4-difluoromethylenedioxybenzyl)piperazine (DF-MDBP), newly detected in illicit products | journal=Forensic Toxicology | date=January 2016 | volume=34 | issue=1 | pages=166–173 | doi=10.1007/s11419-015-0304-7}}</ref> It has a [[Dissociation constant#Protein-ligand binding|binding affinity]] of 0.67nM at the human 5-HT<sub>2A</sub> receptor, making it several times weaker than its [[positional isomer]] [[25I-NBMD]] and a similar potency to [[25I-NBF]].<ref>{{cite journal | vauthors = Braden MR, Parrish JC, Naylor JC, Nichols DE | s2cid = 15840304 | title = Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists | journal = Molecular Pharmacology | volume = 70 | issue = 6 | pages = 1956–64 | date = December 2006 | pmid = 17000863 | doi = 10.1124/mol.106.028720 }}</ref><ref>{{cite thesis | url=https://docs.lib.purdue.edu/dissertations/AAI3287241/ | title=Towards a biophysical understanding of hallucinogen action | pages=1–176 | degree = Ph.D. | publisher = Purdue University | date=2007 | first = Michael Robert | last = Braden | name-list-style = vanc }}</ref>


==Legality==
==Legality==
⚫
25I-NB34MD is illegal in Hungary<ref>[http://www.daath.hu/incoming/designer_jogi_lista_20150903_BSZKI_Daath_kieg.pdf A Magyarországon megjelent, a Kábítószer és Kábítószer-függőség Európai Megfigyelő Központjának Korai Jelzőrendszerébe (EMCDDA EWS) 2005 óta bejelentett ellenőrzött anyagok büntetőjogi vonatkozású besorolása]</ref> and Japan.<ref>{{cite web | url=http://www.mhlw.go.jp/seisakunitsuite/bunya/kenkou_iryou/iyakuhin/yakubuturanyou/dl/meisho.pdf | title=指定薬物名称・構造式一覧（平成27年9月16日現在） | publisher=厚生労働省 | date=16 September 2015 | language=Japanese | accessdate=8 October 2015}}</ref>


== See also ==
===Hungary===
Illegal.<ref>{{cite web | url = http://www.daath.hu/incoming/designer_jogi_lista_20160209_BSZKI_Daath_kieg.pdf | title = A Magyarországon megjelent, a Kábítószer és Kábítószer-függőség Európai Megfigyelő Központjának Korai Jelzőrendszerébe (EMCDDA EWS) 2005 óta bejelentett ellenőrzött anyagok büntetőjogi vonatkozású besorolása | trans-title = Criminal classification of controlled substances published in Hungary and reported to the European Monitoring Center for Drugs and Drug Addiction (EMCDDA EWS) since 2005 | language = Hungarian | publisher = DAATH - A Magyar Pszichedelikus Közösség Honlapja (Homepage of the Hungarian Psychedelic Community) }}</ref>
* [[2CBCB-NBOMe]] (NBOMe-TCB-2)

* [[2CBFly-NBOMe]] (NBOMe-2CB-Fly)
===Japan===
* [[2C-C-NBOMe]] (NBOMe-2CC)
⚫
Illegal.<ref>{{cite web | url=http://www.mhlw.go.jp/seisakunitsuite/bunya/kenkou_iryou/iyakuhin/yakubuturanyou/dl/meisho.pdf | title=指定薬物名称・構造式一覧（平成27年9月16日現在） | publisher=厚生労働省 | date=16 September 2015 | language=Japanese | access-date=8 October 2015}}</ref>
* [[25B-NBOMe]] (NBOMe-2CB)

* [[25I-NBOMe]] (NBOMe-2CI)
===Sweden===
* [[25B-NBOH]]
[[Riksdag|The Riksdag]] added 25I-NB34MD to [[:sv:Narkotikastrafflagen|Narcotic Drugs Punishments Act]] under ''Swedish schedule I'' (''"substances, plant materials and fungi which normally do not have medical use"'') as of June 9, 2015, published by [[Medical Products Agency (Sweden)|Medical Products Agency (MPA)]] in regulation ''LVFS 2015:4'' listed as '''25I-NB34MD''', and '''2-(4-jodo-2,5-dimetoxifenyl)-N-[(3,4-metylendioxifenyl)metyl]etanamin'''.<ref>{{cite web | url = https://lakemedelsverket.se/upload/lvfs/LVFS_2015_4.pdf | title = Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotika | trans-title = Regulations on amendments to the Swedish Medicines Agency's regulations (LVFS 2011: 10) on the list of drugs | language = Swedish | publisher = Läkemedelsverket }}</ref>
* [[25I-NBOH]] (NBOH-2CI)

===United Kingdom===
{{N-benzylphenethylamine-Legality-United Kingdom}}

==Analogues and derivatives==
{{2C-I analogues and derivatives}}


== References ==
== References ==
{{Reflist}}
{{Reflist}}


{{Hallucinogens}}
{{Serotonergics}}
{{Serotonergics}}
{{Phenethylamines}}


[[Category:Psychedelic phenethylamines]]
[[Category:Benzodioxoles]]
[[Category:Designer drugs]]
[[Category:Designer drugs]]
[[Category:Fluoroarenes]]
[[Category:Iodobenzene derivatives]]
[[Category:Iodoarenes]]
[[Category:2C (psychedelics)]]
[[Category:Phenol ethers]]

Latest revision as of 17:33, 4 February 2024

25I-NB34MD
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • N-[(2H-1,3-Benzodioxol-5-yl)methyl]-2-(4-iodo-2,5-dimethoxyphenyl)ethan-1-amine
CAS Number
ChemSpider
UNII
Chemical and physical data
FormulaC18H20INO4
Molar mass441.265 g·mol−1
3D model (JSmol)
  • O1C2=C(OC1)C=C(C=C2)CNCCC3=C(C=C(C(=C3)OC)I)OC
  • InChI=1S/C18H20INO4/c1-21-16-9-14(19)17(22-2)8-13(16)5-6-20-10-12-3-4-15-18(7-12)24-11-23-15/h3-4,7-9,20H,5-6,10-11H2,1-2H3 checkY
  • Key:FWEBGKDUEZRMRQ-UHFFFAOYSA-N checkY

25I-NB34MD (NB34MD-2C-I) is a derivative of the phenethylamine hallucinogen 2C-I, which acts as a potent partial agonist for the human 5-HT2A receptor, and presumably has similar properties to 2C-I.[1] It has a binding affinity of 0.67nM at the human 5-HT2A receptor, making it several times weaker than its positional isomer 25I-NBMD and a similar potency to 25I-NBF.[2][3]

Legality[edit]

Hungary[edit]

Illegal.[4]

Japan[edit]

Illegal.[5]

Sweden[edit]

The Riksdag added 25I-NB34MD to Narcotic Drugs Punishments Act under Swedish schedule I ("substances, plant materials and fungi which normally do not have medical use") as of June 9, 2015, published by Medical Products Agency (MPA) in regulation LVFS 2015:4 listed as 25I-NB34MD, and 2-(4-jodo-2,5-dimetoxifenyl)-N-[(3,4-metylendioxifenyl)metyl]etanamin.[6]

United Kingdom[edit]

This substance is a Class A drug in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause in the Misuse of Drugs Act 1971.[7]

Analogues and derivatives[edit]

Analogues and derivatives of 2C-I:

25I-NB*:

N-(2C)-fentanyl:

References[edit]

  1. ^ Uchiyama N, Kikura-Hanajiri R, Hakamatsuka T (January 2016). "A phenethylamine derivative 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(3,4-methylenedioxyphenyl)methyl]ethanamine (25I-NB34MD) and a piperazine derivative 1-(3,4-difluoromethylenedioxybenzyl)piperazine (DF-MDBP), newly detected in illicit products". Forensic Toxicology. 34 (1): 166–173. doi:10.1007/s11419-015-0304-7. S2CID 20296244.
  2. ^ Braden MR, Parrish JC, Naylor JC, Nichols DE (December 2006). "Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists". Molecular Pharmacology. 70 (6): 1956–64. doi:10.1124/mol.106.028720. PMID 17000863. S2CID 15840304.
  3. ^ Braden MR (2007). Towards a biophysical understanding of hallucinogen action (Ph.D. thesis). Purdue University. pp. 1–176.
  4. ^ "A Magyarországon megjelent, a Kábítószer és Kábítószer-függőség Európai Megfigyelő Központjának Korai Jelzőrendszerébe (EMCDDA EWS) 2005 óta bejelentett ellenőrzött anyagok büntetőjogi vonatkozású besorolása" [Criminal classification of controlled substances published in Hungary and reported to the European Monitoring Center for Drugs and Drug Addiction (EMCDDA EWS) since 2005] (PDF) (in Hungarian). DAATH - A Magyar Pszichedelikus Közösség Honlapja (Homepage of the Hungarian Psychedelic Community).
  5. ^ "指定薬物名称・構造式一覧（平成27年9月16日現在）" (PDF) (in Japanese). 厚生労働省. 16 September 2015. Retrieved 8 October 2015.
  6. ^ "Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotika" [Regulations on amendments to the Swedish Medicines Agency's regulations (LVFS 2011: 10) on the list of drugs] (PDF) (in Swedish). Läkemedelsverket.
  7. ^ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Statutory Instruments 2014 No. 1106. www.legislation.gov.uk.
  8. ^ "Explore N-(2C-I)-Fentanyl | PiHKAL · info". isomerdesign.com.
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