25N-NBOMe: Difference between revisions

25N-NBOMe
Names
	IUPAC name 2-(2,5-Dimethoxy-4-nitrophenyl)-N-(2-methoxybenzyl)ethanamine
	Other names 2C-N-NBOMe, NBOMe-2C-N
Identifiers
CAS Number	1354632-03-3;
3D model (JSmol)	Interactive image;
ChemSpider	52085577;
PubChem CID	118536028;
UNII	0G7SSW2N0S ;
CompTox Dashboard (EPA)	DTXSID501014186 ;
	InChI InChI=1S/C18H22N2O5/c1-23-16-7-5-4-6-14(16)12-19-9-8-13-10-18(25-3)15(20(21)22)11-17(13)24-2/h4-7,10-11,19H,8-9,12H2,1-3H3 Key: TXCKTIBHURMASQ-UHFFFAOYSA-N;
	SMILES COC1=C(CCNCC2=C(OC)C=CC=C2)C=C(OC)C([N+]([O-])=O)=C1;
Properties
Chemical formula	C18H22N2O5
Molar mass	346.383 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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Revision as of 13:55, 9 January 2019

25N-NBOMe (2C-N-NBOMe, NBOMe-2C-N) is a derivative of the hallucinogen 2C-N. The pharmacological properties of 25N-NBOMe have not been described in the scientific literature, but it is believed to act in a similar manner to related compounds such as 25I-NBOMe and 25C-NBOMe, which are potent agonists at the 5HT_2A receptor.^[1]^[2] 25N-NBOMe has been sold as a street drug and has only been described in the literature in terms of identification by forensic analysis.^[3]^[4]

Legality

25N-NBOMe is illegal in Alabama,^[5] and Hungary.^[6]

Sweden

The Riksdag added 25N-NBOMe to Narcotic Drugs Punishments Act under swedish schedule I ("substances, plant materials and fungi which normally do not have medical use") as of January 16, 2015, published by Medical Products Agency (MPA) in regulation LVFS 2014:11 listed as 25N-NBOMe, and 2-(2,5-dimetoxi-4-nitrofenyl)-N-(2-metoxibensyl)etanamin.^[7]

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.^[8]

References

^ Hansen, M.; Phonekeo, K.; Paine, J. S.; Leth-Petersen, S.; Begtrup, M.; Bräuner-Osborne, H.; Kristensen, J. L. (2014). "Synthesis and Structure-Activity Relationships of N-Benzyl Phenethylamines as 5-HT_2A/2C Agonists". ACS Chemical Neuroscience. 5 (3): 243–9. doi:10.1021/cn400216u. PMC 3963123. PMID 24397362.
^ Hansen, M. Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain. PhD Thesis, University of Copenhagen, 2011.
^ Casale, John F.; Hays, Patrick A. (2012). "Characterization of Eleven 2,5-Dimethoxy-N-(2-methoxybenzyl)phenethylamine (NBOMe) Derivatives and Differentiation from their 3- and 4-Methoxybenzyl Analogues - Part I" (PDF). Microgram Journal. 9 (2): 84–109. Retrieved 14 January 2014.
^ Uchiyama N, Shimokawa Y, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y (2014). "Two new synthetic cannabinoids, AM-2201 benzimidazole analog (FUBIMINA) and (4-methylpiperazin-1-yl)(1-pentyl-1H-indol-3-yl)methanone (MEPIRAPIM), and three phenethylamine derivatives, 25H-NBOMe 3,4,5-trimethoxybenzyl analog, 25B-NBOMe, and 2C-N-NBOMe, identified in illegal products". Forensic Toxicology. 32 (1): 105–115. doi:10.1007/s11419-013-0217-2.
^ Alabama Senate Bill SB 333: Controlled Substances
^ A Daath.hu kiegészítése a BSZKI "designer jogi listáján" nem szereplő, de az UP jegyzék 1.-4. szerkezeti leírásainak megfelelő, illetve az 5. felsorolásában szereplő néhány anyagról
^ https://lakemedelsverket.se/upload/lvfs/LVFS_2014_11.pdf
^ "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Statutory Instruments 2014 No. 1106. www.legislation.gov.uk.

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[1] Hansen, M.; Phonekeo, K.; Paine, J. S.; Leth-Petersen, S.; Begtrup, M.; Bräuner-Osborne, H.; Kristensen, J. L. (2014). "Synthesis and Structure-Activity Relationships of N-Benzyl Phenethylamines as 5-HT_2A/2C Agonists". ACS Chemical Neuroscience. 5 (3): 243–9. doi:10.1021/cn400216u. PMC 3963123. PMID 24397362.

[2] Hansen, M. Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain. PhD Thesis, University of Copenhagen, 2011.

[3] Casale, John F.; Hays, Patrick A. (2012). "Characterization of Eleven 2,5-Dimethoxy-N-(2-methoxybenzyl)phenethylamine (NBOMe) Derivatives and Differentiation from their 3- and 4-Methoxybenzyl Analogues - Part I" (PDF). Microgram Journal. 9 (2): 84–109. Retrieved 14 January 2014.

[4] Uchiyama N, Shimokawa Y, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y (2014). "Two new synthetic cannabinoids, AM-2201 benzimidazole analog (FUBIMINA) and (4-methylpiperazin-1-yl)(1-pentyl-1H-indol-3-yl)methanone (MEPIRAPIM), and three phenethylamine derivatives, 25H-NBOMe 3,4,5-trimethoxybenzyl analog, 25B-NBOMe, and 2C-N-NBOMe, identified in illegal products". Forensic Toxicology. 32 (1): 105–115. doi:10.1007/s11419-013-0217-2.

[5] Alabama Senate Bill SB 333: Controlled Substances

[6] A Daath.hu kiegészítése a BSZKI "designer jogi listáján" nem szereplő, de az UP jegyzék 1.-4. szerkezeti leírásainak megfelelő, illetve az 5. felsorolásában szereplő néhány anyagról

[7] ttps://lakemedelsverket.se/upload/lvfs/LVFS_2014_11.pdf

[8] "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Statutory Instruments 2014 No. 1106. www.legislation.gov.uk.

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@@ Line 30: / Line 30: @@
 '''25N-NBOMe''' ('''2C-N-NBOMe''', '''NBOMe-2C-N''') is a [[derivative (chemistry)|derivative]] of the [[hallucinogen]] [[2C-N]]. The pharmacological properties of 25N-NBOMe have not been described in the scientific literature, but it is believed to act in a similar manner to related compounds such as [[25I-NBOMe]] and [[25C-NBOMe]], which are potent [[agonist]]s at the [[5HT2A receptor|5HT<sub>2A</sub>]] [[Receptor (biochemistry)|receptor]].<ref>{{Cite journal | last1 = Hansen | first1 = M. | last2 = Phonekeo | first2 = K. | last3 = Paine | first3 = J. S. | last4 = Leth-Petersen | first4 = S. | last5 = Begtrup | first5 = M. | last6 = Bräuner-Osborne | first6 = H. | last7 = Kristensen | first7 = J. L. | doi = 10.1021/cn400216u | title = Synthesis and Structure-Activity Relationships of N-Benzyl Phenethylamines as 5-HT<sub>2A/2C</sub> Agonists | journal = ACS Chemical Neuroscience | volume = 5 | issue = 3 | pages = 243–9  | year = 2014 | pmid = 24397362| pmc = 3963123
-}}</ref><ref>[http://bitnest.ca/external.php?id=%2518%253A3%25172%251BE%2524K%255BG%2521%2524%257D%2504%2504V Hansen, M. Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain. PhD Thesis, University of Copenhagen, 2011.]</ref> 25N-NBOMe has been sold as a street drug and has only been described in the literature in terms of identification by forensic analysis.<ref>{{cite journal|last=Casale|first=John F.|author2=Hays, Patrick A.|title=Characterization of Eleven 2,5-Dimethoxy-N-(2-methoxybenzyl)phenethylamine (NBOMe) Derivatives and Differentiation from their  3- and 4-Methoxybenzyl Analogues - Part I|journal=Microgram Journal|year=2012|volume=9|issue=2|pages=84–109|url=http://www.justice.gov/dea/pr/microgram-journals/2012/mj9_84-109.pdf|accessdate=14 January 2014}}</ref><ref>{{cite journal | url=https://link.springer.com/article/10.1007%2Fs11419-013-0217-2 | title=Two new synthetic cannabinoids, AM-2201 benzimidazole analog (FUBIMINA) and (4-methylpiperazin-1-yl)(1-pentyl-1H-indol-3-yl)methanone (MEPIRAPIM), and three phenethylamine derivatives, 25H-NBOMe 3,4,5-trimethoxybenzyl analog, 25B-NBOMe, and 2C-N-NBOMe, identified in illegal products |vauthors=Uchiyama N, Shimokawa Y, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y | journal=Forensic Toxicology | year=2014 | volume=32 | issue=1 | pages=105–115 | doi=10.1007/s11419-013-0217-2}}</ref>
+}}</ref><ref>[http://bitnest.ca/external.php?id=%2518%253A3%25172%251BE%2524K%255BG%2521%2524%257D%2504%2504V Hansen, M. Design and Synthesis of Selective Serotonin Receptor Agonists for Positron Emission Tomography Imaging of the Brain. PhD Thesis, University of Copenhagen, 2011.]</ref> 25N-NBOMe has been sold as a street drug and has only been described in the literature in terms of identification by forensic analysis.<ref>{{cite journal|last=Casale|first=John F.|author2=Hays, Patrick A.|title=Characterization of Eleven 2,5-Dimethoxy-N-(2-methoxybenzyl)phenethylamine (NBOMe) Derivatives and Differentiation from their  3- and 4-Methoxybenzyl Analogues - Part I|journal=Microgram Journal|year=2012|volume=9|issue=2|pages=84–109|url=http://www.justice.gov/dea/pr/microgram-journals/2012/mj9_84-109.pdf|accessdate=14 January 2014}}</ref><ref>{{cite journal | title=Two new synthetic cannabinoids, AM-2201 benzimidazole analog (FUBIMINA) and (4-methylpiperazin-1-yl)(1-pentyl-1H-indol-3-yl)methanone (MEPIRAPIM), and three phenethylamine derivatives, 25H-NBOMe 3,4,5-trimethoxybenzyl analog, 25B-NBOMe, and 2C-N-NBOMe, identified in illegal products |vauthors=Uchiyama N, Shimokawa Y, Matsuda S, Kawamura M, Kikura-Hanajiri R, Goda Y | journal=Forensic Toxicology | year=2014 | volume=32 | issue=1 | pages=105–115 | doi=10.1007/s11419-013-0217-2}}</ref>
 ==Legality==

v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA ZDCM-04 Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D-Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (Levodopa) L-DOPS (Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine

Revision as of 13:55, 9 January 2019

Legality

Sweden

United Kingdom

See also

References