25I-NB34MD

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]

25I-NB34MD
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
IUPAC name
  • 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)
SMILES
  • O1C2=C(OC1)C=C(C=C2)CNCCC3=C(C=C(C(=C3)OC)I)OC
InChI
  • 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 Y
  • Key:FWEBGKDUEZRMRQ-UHFFFAOYSA-N Y

Legality

Hungary

Illegal.[4]

Japan

Illegal.[5]

Sweden

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

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

Analogues and derivatives of 2C-I:

25I-NB*:

References
  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". www.legislation.gov.uk.
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