25I-NB34MD

25I-NB34MD
Clinical data
ATC code	none;
Legal status
Legal status	UK: Class A;
Identifiers
	IUPAC name N-[(2H-1,3-Benzodioxol-5-yl)methyl]-2-(4-iodo-2,5-dimethoxyphenyl)ethan-1-amine;
CAS Number	1391497-81-6 ;
ChemSpider	58191429 ;
UNII	R7X848UW5A;
Chemical and physical data
Formula	C18H20INO4
Molar mass	441.265 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:FWEBGKDUEZRMRQ-UHFFFAOYSA-N ;

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-HT_2A receptor, and presumably has similar properties to 2C-I.^[1] It has a binding affinity of 0.67nM at the human 5-HT_2A receptor, making it several times weaker than its positional isomer 25I-NBMD and a similar potency to 25I-NBF.^[2]^[3]

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*:

N-(2C)-fentanyl:

N-(2C-I) fentanyl^[8]

References

^ 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.
^ 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.
^ Braden MR (2007). Towards a biophysical understanding of hallucinogen action (Ph.D. thesis). Purdue University. pp. 1–176.
^ "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).
^ "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.
^ "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.
^ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Statutory Instruments 2014 No. 1106. www.legislation.gov.uk.
^ "Explore N-(2C-I)-Fentanyl | PiHKAL · info". isomerdesign.com.

[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.

[1]

[2]

[3]

[4]

[5]

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[7]

[8]

Clinical data

ATC code	none
Legal status
Legal status	UK: Class A
Identifiers
IUPAC name N-[(2H-1,3-Benzodioxol-5-yl)methyl]-2-(4-iodo-2,5-dimethoxyphenyl)ethan-1-amine
CAS Number	1391497-81-6^Y
ChemSpider	58191429^Y
UNII	R7X848UW5A
Chemical and physical data
Formula	C₁₈H₂₀INO₄
Molar mass	441.265 g·mol⁻¹
3D model (JSmol)	Interactive image
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