25-NB

The 25-NB (25x-NBx) series, sometimes alternatively referred to as the NBOMe compounds, is a family of serotonergic psychedelics.[1] They are substituted phenethylamines and were derived from the 2C family.[1] They act as selective agonists of the serotonin 5-HT_2A receptor.[2][3][4][5][6][7][8] The 25-NB family is unique relative to other classes of psychedelics in that they are, generally speaking, extremely potent and relatively selective for the 5-HT_2A receptor.[1]

25I-NBOMe, the most well-known 25-NB derivative.

Chemical structure

The 25-NB compounds are mostly N-benzylphenethylamines,[1][9] though in some cases the phenyl ring of the N-benzyl group is replaced by other heterocycles such as thiophene, pyridine, furan, tetrahydrofuran, benzodioxole or naphthalene, among others.[10][11]

Generally speaking, they have methoxy groups at the 2 and 5 positions of the phenyl ring, a substitution such as a halogen or alkyl group at the 4 position of the phenyl ring, and a methoxy or other substitution (e.g., hydroxyl, fluoro) at the 2 position of the N-benzyl ring.[1] More rarely, other substitution patterns may be present [12][13] (see e.g. NBOMe-mescaline, 25G-NBOMe, 2CBFly-NBOMe, 25C-NB3OMe). They differ from the 2C series by the presence of the N-benzyl moiety.[1]

Rarely an alpha-methyl group is present making them N-benzyl amphetamines rather than N-benzyl phenethylamines, but this greatly reduces potency and activity. However in some cases where a side chain methyl group is cyclised back to the ring (e.g. in 2CBCB-NBOMe) or links the two alpha positions (e.g. in DMBMPP), this can improve selectivity for the 5-HT_2A receptor subtype.[14]

List of 25-NB derivatives

General structure of 25-NB derivatives, where R is usually 2,5-dimethoxy-4-(alkyl or halogen), R₁ is usually H but rarely methyl, and Cyc is usually 2-substituted phenyl but can be other heterocycles

This list includes notable compounds representative of most of the structural variations that have been explored in this series, but is by no means exhaustive. Many derivatives invented for scientific study into the structure-activity relationships of 5-HT₂ receptor agonists have never appeared as designer drugs, while conversely some derivatives that have appeared as designer drugs are structurally novel and of unknown pharmacological activity (e.g. C30-NBOMe, 5-APB-NBOMe).

Chemical structure	Common name	Chemical name	CAS number	R	R1	Cyc
	25B-NB	N-benzyl-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane	155639-26-2	2,5-dimethoxy-4-bromo	H	phenyl
	25C-NB	N-benzyl-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane	1391487-65-2	2,5-dimethoxy-4-chloro	H	phenyl
	25I-NB	N-benzyl-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane	919797-18-5	2,5-dimethoxy-4-iodo	H	phenyl
	25I-NMeTh	N-[(thiophen-2-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane	1391499-03-8	2,5-dimethoxy-4-iodo	H	thiophen-2-yl
	25B-NMePyr	N-[(pyridin-2-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane	1391499-21-0	2,5-dimethoxy-4-bromo	H	pyridin-2-yl
	25I-NMeFur	N-[(furan-2-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane	1391498-93-3	2,5-dimethoxy-4-iodo	H	furan-2-yl
	25I-NMeTHF	N-[(tetrahydrofuran-2-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane		2,5-dimethoxy-4-iodo	H	tetrahydrofuran-2-yl
	25B-NBF	N-(2-fluorobenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane	1539266-17-5	2,5-dimethoxy-4-bromo	H	2-fluorophenyl
	25B-NBOH	N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane	1335331-46-8	2,5-dimethoxy-4-bromo	H	2-hydroxyphenyl
	25B-NBOMe	N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane	1026511-90-9	2,5-dimethoxy-4-bromo	H	2-methoxyphenyl
	25B-NB23DM	N-(2,3-dimethoxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane	1391493-68-7	2,5-dimethoxy-4-bromo	H	2,3-dimethoxyphenyl
	25B-NB25DM	N-(2,5-dimethoxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane		2,5-dimethoxy-4-bromo	H	2,5-dimethoxyphenyl
	25B-NMe7BF	N-[(benzofuran-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane	1391492-46-8	2,5-dimethoxy-4-bromo	H	benzofuran-7-yl
	25B-NMe7DHBF	N-[(2,3-dihydrobenzofuran-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane	1391492-40-2	2,5-dimethoxy-4-bromo	H	2,3-dihydrobenzofuran-7-yl
	25B-NMe7BT	N-[(benzothiophen-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane	1391492-59-3	2,5-dimethoxy-4-bromo	H	benzothiophen-7-yl
	25B-NMe7Box	N-[(benzoxazol-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane	1391498-73-9	2,5-dimethoxy-4-bromo	H	benzoxazol-7-yl
	25B-NMe7Ind	N-[(indol-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane	1391498-28-4	2,5-dimethoxy-4-bromo	H	indol-7-yl
	25B-NMe7Indz	N-[(indazol-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane	1391498-43-3	2,5-dimethoxy-4-bromo	H	indazol-7-yl
	25B-NMe7Bim	N-[(benzimidazol-7-yl)methyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane	1391498-62-6	2,5-dimethoxy-4-bromo	H	benzimidazol-7-yl
	FECIMBI-36	N-[(2-fluoroethoxy)benzyl]-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane		2,5-dimethoxy-4-bromo	H	2-(2-fluoroethoxy)phenyl
	DOB-NBOMe	N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminopropane		2,5-dimethoxy-4-bromo	methyl	2-methoxyphenyl
	25C-NB3OMe	N-(3-methoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane	1566571-34-3	2,5-dimethoxy-4-chloro	H	3-methoxyphenyl
	25C-NB4OMe	N-(4-methoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane	1566571-35-4	2,5-dimethoxy-4-chloro	H	4-methoxyphenyl
	C30-NBOMe	N-(3,4,5-trimethoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane	1445574-98-0	2,5-dimethoxy-4-chloro	H	3,4,5-trimethoxyphenyl
	25C-NBF	N-(2-fluorobenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane	1539266-21-1	2,5-dimethoxy-4-chloro	H	2-fluorophenyl
	25C-NBCl	N-(2-chlorobenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane		2,5-dimethoxy-4-chloro	H	2-chlorophenyl
	25C-NBOH	N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane	1391488-16-6	2,5-dimethoxy-4-chloro	H	2-hydroxyphenyl
	25C-NBOMe	N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane	1227608-02-7	2,5-dimethoxy-4-chloro	H	2-methoxyphenyl
	25C-NBOEt	N-(2-ethoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane		2,5-dimethoxy-4-chloro	H	2-ethoxyphenyl
	25C-NBOiPr	N-(2-isopropoxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane		2,5-dimethoxy-4-chloro	H	2-isopropoxyphenyl
	25F-NBOMe	N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-fluorophenyl)-2-aminoethane	1373917-84-0	2,5-dimethoxy-4-fluoro	H	2-methoxyphenyl
	25CN-NBOH	N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-cyanophenyl)-2-aminoethane	1539266-32-4	2,5-dimethoxy-4-cyano	H	2-hydroxyphenyl
	25CN-NBOMe	N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-cyanophenyl)-2-aminoethane	1354632-16-8	2,5-dimethoxy-4-cyano	H	2-methoxyphenyl
	25D-NBOMe	N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-methylphenyl)-2-aminoethane	1354632-02-2	2,5-dimethoxy-4-methyl	H	2-methoxyphenyl
	25D-NBOH	N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-methylphenyl)-2-aminoethane	1391488-44-0	2,5-dimethoxy-4-methyl	H	2-hydroxyphenyl
	25E-NBOMe	N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-ethylphenyl)-2-aminoethane	1354632-14-6	2,5-dimethoxy-4-ethyl	H	2-methoxyphenyl
	25E-NBOH	N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-ethylphenyl)-2-aminoethane	1391489-79-4	2,5-dimethoxy-4-ethyl	H	2-hydroxyphenyl
	25G-NBOMe	N-(2-methoxybenzyl)-1-(2,5-dimethoxy-3,4-dimethylphenyl)-2-aminoethane	1354632-65-7	2,5-dimethoxy-3,4-dimethyl	H	2-methoxyphenyl
	25H-NBOMe	N-(2-methoxybenzyl)-1-(2,5-dimethoxyphenyl)-2-aminoethane	1566571-52-5	2,5-dimethoxy	H	2-methoxyphenyl
	25I-NB34MD	N-(3,4-methylenedioxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane	1391497-81-6	2,5-dimethoxy-4-iodo	H	3,4-methylenedioxyphenyl
	25I-NB3OMe	N-(3-methoxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane	1566571-40-1	2,5-dimethoxy-4-iodo	H	3-methoxyphenyl
	25I-NB4OMe	N-(4-methoxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane	1566571-41-2	2,5-dimethoxy-4-iodo	H	4-methoxyphenyl
	25I-NBF	N-(2-fluorobenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane	919797-21-0	2,5-dimethoxy-4-iodo	H	2-fluorophenyl
	25I-NBBr	N-(2-bromobenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane	1648649-98-2	2,5-dimethoxy-4-iodo	H	2-bromophenyl
	25I-NBTFM	N-[2-(trifluoromethyl)benzyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane		2,5-dimethoxy-4-iodo	H	2-(trifluoromethyl)phenyl
	25I-NBMD	N-(2,3-methylenedioxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane	919797-25-4	2,5-dimethoxy-4-iodo	H	2,3-methylenedioxyphenyl
	25B-NBMD	N-(2,3-methylenedioxybenzyl)-1-(2,5-dimethoxy-4-bromophenyl)-2-aminoethane	1354632-19-1	2,5-dimethoxy-4-bromo	H	2,3-methylenedioxyphenyl
	25C-NBMD	N-(2,3-methylenedioxybenzyl)-1-(2,5-dimethoxy-4-chlorophenyl)-2-aminoethane	1373879-26-5	2,5-dimethoxy-4-chloro	H	2,3-methylenedioxyphenyl
	25D-NBMD	N-(2,3-methylenedioxybenzyl)-1-(2,5-dimethoxy-4-methylphenyl)-2-aminoethane	1391488-97-3	2,5-dimethoxy-4-methyl	H	2,3-methylenedioxyphenyl
	25I-NBOH	N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane	919797-20-9	2,5-dimethoxy-4-iodo	H	2-hydroxyphenyl
	25I-NBOMe	N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane	919797-19-6	2,5-dimethoxy-4-iodo	H	2-methoxyphenyl
	DOI-NBOMe	N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane		2,5-dimethoxy-4-iodo	methyl	2-methoxyphenyl
	25I-NBMeOH	N-[2-(hydroxymethyl)benzyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane	1391494-71-5	2,5-dimethoxy-4-iodo	H	2-(hydroxymethyl)phenyl
	25I-NBAm	N-[2-(carbamoyl)benzyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane	1391494-85-1	2,5-dimethoxy-4-iodo	H	2-(carbamoyl)phenyl
	25I-NMe7DHBF	N-[(2,3-dihydrobenzofuran-7-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane		2,5-dimethoxy-4-iodo	H	2,3-dihydrobenzofuran-7-yl
	25I-N2Nap1OH	N-[(1-hydroxynaphthalen-2-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane		2,5-dimethoxy-4-iodo	H	1-hydroxynaphthalen-2-yl
	25I-N3MT2M	N-[(3-methoxythiophen-2-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane	1354632-66-8	2,5-dimethoxy-4-iodo	H	3-methoxythiophen-2-yl
	25I-N4MT3M	N-[(4-methoxythiophen-3-yl)methyl]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane	1354632-73-7	2,5-dimethoxy-4-iodo	H	4-methoxythiophen-3-yl
	25iP-NBOMe	N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-isopropylphenyl)-2-aminoethane	1391487-83-4	2,5-dimethoxy-4-isopropyl	H	2-methoxyphenyl
	25N-NBOMe	N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-nitrophenyl)-2-aminoethane	1354632-03-3	2,5-dimethoxy-4-nitro	H	2-methoxyphenyl
	25P-NBOMe	N-(2-methoxybenzyl)-1-(2,5-dimethoxy-4-propylphenyl)-2-aminoethane	1391489-07-8	2,5-dimethoxy-4-propyl	H	2-methoxyphenyl
	25P-NBOH	N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-propylphenyl)-2-aminoethane	1391490-34-8	2,5-dimethoxy-4-propyl	H	2-hydroxyphenyl
	25TFM-NBOMe	N-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-(trifluoromethyl)phenyl]-2-aminoethane	1027161-33-6	2,5-dimethoxy-4-(trifluoromethyl)	H	2-methoxyphenyl
	25T-NBOMe	N-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-(methylthio)phenyl]-2-aminoethane	1539266-47-1	2,5-dimethoxy-4-(methylthio)	H	2-methoxyphenyl
	25T2-NBOMe	N-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-(ethylthio)phenyl]-2-aminoethane		2,5-dimethoxy-4-(ethylthio)	H	2-methoxyphenyl
	25T4-NBOMe	N-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-(isopropylthio)phenyl]-2-aminoethane	1354632-17-9	2,5-dimethoxy-4-(isopropylthio)	H	2-methoxyphenyl
	25T7-NBOMe	N-(2-methoxybenzyl)-1-[2,5-dimethoxy-4-(propylthio)phenyl]-2-aminoethane	1539266-55-1	2,5-dimethoxy-4-(propylthio)	H	2-methoxyphenyl
	25T7-NBOH	N-(2-hydroxybenzyl)-1-[2,5-dimethoxy-4-(propylthio)phenyl]-2-aminoethane	1354632-41-9	2,5-dimethoxy-4-(propylthio)	H	2-hydroxyphenyl
	NBOMe-mescaline	N-(2-methoxybenzyl)-1-(3,4,5-trimethoxyphenyl)-2-aminoethane	1354632-01-1	3,4,5-trimethoxy	H	2-methoxyphenyl
	NBOMe-escaline	N-(2-methoxybenzyl)-1-(3,5-dimethoxy-4-ethoxyphenyl)-2-aminoethane		3,5-dimethoxy-4-ethoxy	H	2-methoxyphenyl
	MDPEA-NBOMe	N-(2-methoxybenzyl)-1-(3,4-methylenedioxyphenyl)-2-aminoethane		3,4-methylenedioxy	H	2-methoxyphenyl
	MDBZ	N-benzyl-1-(3,4-methylenedioxyphenyl)-2-aminopropane	65033-29-6	3,4-methylenedioxy	methyl	phenyl
	Clobenzorex	N-(2-chlorobenzyl)-1-phenyl-2-aminopropane	13364-32-4	H	methyl	2-chlorophenyl
	4-EA-NBOMe	N-(2-methoxybenzyl)-1-(4-ethylphenyl)-2-aminopropane		4-ethyl	methyl	2-methoxyphenyl
	5-APB-NBOMe	N-(2-methoxybenzyl)-1-(benzofuran-5-yl)-2-aminopropane		benzofuran-5-yl instead of phenyl	methyl	2-methoxyphenyl

Similar compounds with related structures are also known including;

Chemical structure	Common name	Chemical name	CAS number
	25B-N1POMe	N-[1-(2-methoxyphenyl)ethyl]-2,5-dimethoxy-4-bromophenethylamine	1335331-49-1 (R) 1335331-51-5 (S)
	2C-B-AN [15]	2-phenyl-2-[2-(2,5-dimethoxy-4-bromophenyl)ethylamino]acetonitrile
	2CBCB-NBOMe	N-[(3-bromo-2,5-dimethoxy-bicyclo[4,2,0]octa-1,3,5-trien-7-yl)methyl]-1-(2-methoxyphenyl)methanamine	1354634-09-5
	2CBFly-NBOMe	N-(2-methoxybenzyl)-1-(8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b’]difuran-4-yl)-2-aminoethane	1335331-42-4
	2C-B-DRAGONFLY-NBOH	N-(2-hydroxybenzyl)-1-(8-bromobenzo[1,2-b:4,5-b’]difuran-4-yl)-2-aminoethane	1335331-45-7
	2C-B-FLY-NB2EtO5Cl [16]	N-(2-ethoxy-5-chlorobenzyl)-1-(8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b’]difuran-4-yl)-2-aminoethane
	DMBMPP	(S,S)-2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine	1391499-52-7
	25B-NAcPip	2-{[2-(4-bromo-2,5-dimethoxyphenyl)ethyl]amino}-1-(piperidin-1-yl)ethanone
	ZDCM-04	1,3-dimethyl-7-{2-[1-(2,5-dimethoxy-4-chlorophenyl)propan-2-ylamino]ethyl}purine-2,6-dione
	RH-34	3-[2-(2-methoxybenzylamino)ethyl]-1H-quinazoline-2,4-dione	1028307-48-3
	5MT-NBOMe [17]	N-(2-methoxybenzyl)-5-methoxytryptamine

Legality

United Kingdom

A large number of substances in the 25-NB class are Class A drugs in the United Kingdom as a result of the N-benzylphenethylamine catch-all clause in the Misuse of Drugs Act 1971[18] or are otherwise covered by the Psychoactive Substances Act 2016.[19]

See also

• 2C family
• DOx family

External links

• VICE In-house Chemist Hamilton Morris on the Dangers of the NBOMe Hallucinogen

References

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2. Pertz, HH; Rheineck, A; Elz, S (1999-01-01). "N-Benzylated derivatives of the hallucinogenic drugs mescaline and escaline as partial agonists at rat vascular 5-HT2A receptors". Naunyn-Schmiedeberg's Archives of Pharmacology. 359: R29.
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