25-NB


The 25-NB series, sometimes alternatively referred to as the NBOMe compounds, is a family of serotonergic psychedelics. They are substituted phenethylamines and were derived from the 2C family. They act as selective agonists of the serotonin 5-HT2A receptor. 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-HT2A receptor.

Chemical structure

The 25-NB compounds are mostly N-benzylphenethylamines, 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.
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 at the 2 position of the N-benzyl ring. More rarely, other substitution patterns may be present . They differ from the 2C series by the presence of the N-benzyl moiety.
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 or links the two alpha positions, this can improve selectivity for the 5-HT2A receptor subtype.

List of 25-NB derivatives

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.
Chemical structureCommon nameChemical nameCAS numberRR1Cyc
25B-NBN-benzyl-1--2-aminoethane155639-26-22,5-dimethoxy-4-bromoHphenyl
25C-NBN-benzyl-1--2-aminoethane1391487-65-22,5-dimethoxy-4-chloroHphenyl
25I-NBN-benzyl-1--2-aminoethane919797-18-52,5-dimethoxy-4-iodoHphenyl
25I-NMeThN--1--2-aminoethane1391499-03-82,5-dimethoxy-4-iodoHthiophen-2-yl
25B-NMePyrN--1--2-aminoethane1391499-21-02,5-dimethoxy-4-bromoHpyridin-2-yl
25I-NMeFurN--1--2-aminoethane1391498-93-32,5-dimethoxy-4-iodoHfuran-2-yl
25I-NMeTHFN--1--2-aminoethane2,5-dimethoxy-4-iodoHtetrahydrofuran-2-yl
25B-NBFN--1--2-aminoethane1539266-17-52,5-dimethoxy-4-bromoH2-fluorophenyl
25B-NBOHN--1--2-aminoethane1335331-46-82,5-dimethoxy-4-bromoH2-hydroxyphenyl
25B-NBOMeN--1--2-aminoethane1026511-90-92,5-dimethoxy-4-bromoH2-methoxyphenyl
25B-NB23DMN--1--2-aminoethane1391493-68-72,5-dimethoxy-4-bromoH2,3-dimethoxyphenyl
25B-NB25DMN--1--2-aminoethane2,5-dimethoxy-4-bromoH2,5-dimethoxyphenyl
25B-NMe7BFN--1--2-aminoethane1391492-46-82,5-dimethoxy-4-bromoHbenzofuran-7-yl
25B-NMe7DHBFN--1--2-aminoethane1391492-40-22,5-dimethoxy-4-bromoH2,3-dihydrobenzofuran-7-yl
25B-NMe7BTN--1--2-aminoethane1391492-59-32,5-dimethoxy-4-bromoHbenzothiophen-7-yl
25B-NMe7BoxN--1--2-aminoethane1391498-73-92,5-dimethoxy-4-bromoHbenzoxazol-7-yl
25B-NMe7IndN--1--2-aminoethane1391498-28-42,5-dimethoxy-4-bromoHindol-7-yl
25B-NMe7IndzN--1--2-aminoethane1391498-43-32,5-dimethoxy-4-bromoHindazol-7-yl
25B-NMe7BimN--1--2-aminoethane1391498-62-62,5-dimethoxy-4-bromoHbenzimidazol-7-yl
FECIMBI-36N--1--2-aminoethane2,5-dimethoxy-4-bromoH2-phenyl
DOB-NBOMeN--1--2-aminopropane2,5-dimethoxy-4-bromomethyl2-methoxyphenyl
25C-NB3OMeN--1--2-aminoethane1566571-34-32,5-dimethoxy-4-chloroH3-methoxyphenyl
25C-NB4OMeN--1--2-aminoethane1566571-35-42,5-dimethoxy-4-chloroH4-methoxyphenyl
C30-NBOMeN--1--2-aminoethane1445574-98-02,5-dimethoxy-4-chloroH3,4,5-trimethoxyphenyl
25C-NBFN--1--2-aminoethane1539266-21-12,5-dimethoxy-4-chloroH2-fluorophenyl
25C-NBClN--1--2-aminoethane2,5-dimethoxy-4-chloroH2-chlorophenyl
25C-NBOHN--1--2-aminoethane1391488-16-62,5-dimethoxy-4-chloroH2-hydroxyphenyl
25C-NBOMeN--1--2-aminoethane1227608-02-72,5-dimethoxy-4-chloroH2-methoxyphenyl
25C-NBOEtN--1--2-aminoethane2,5-dimethoxy-4-chloroH2-ethoxyphenyl
25C-NBOiPrN--1--2-aminoethane2,5-dimethoxy-4-chloroH2-isopropoxyphenyl
25F-NBOMeN--1--2-aminoethane1373917-84-02,5-dimethoxy-4-fluoroH2-methoxyphenyl
25CN-NBOHN--1--2-aminoethane1539266-32-42,5-dimethoxy-4-cyanoH2-hydroxyphenyl
25CN-NBOMeN--1--2-aminoethane1354632-16-82,5-dimethoxy-4-cyanoH2-methoxyphenyl
25D-NBOMeN--1--2-aminoethane1354632-02-22,5-dimethoxy-4-methylH2-methoxyphenyl
25D-NBOHN--1--2-aminoethane1391488-44-02,5-dimethoxy-4-methylH2-hydroxyphenyl
25E-NBOMeN--1--2-aminoethane1354632-14-62,5-dimethoxy-4-ethylH2-methoxyphenyl
25E-NBOHN--1--2-aminoethane1391489-79-42,5-dimethoxy-4-ethylH2-hydroxyphenyl
25G-NBOMeN--1--2-aminoethane1354632-65-72,5-dimethoxy-3,4-dimethylH2-methoxyphenyl
25H-NBOMeN--1--2-aminoethane1566571-52-52,5-dimethoxyH2-methoxyphenyl
25I-NB34MDN--1--2-aminoethane1391497-81-62,5-dimethoxy-4-iodoH3,4-methylenedioxyphenyl
25I-NB3OMeN--1--2-aminoethane1566571-40-12,5-dimethoxy-4-iodoH3-methoxyphenyl
25I-NB4OMeN--1--2-aminoethane1566571-41-22,5-dimethoxy-4-iodoH4-methoxyphenyl
25I-NBFN--1--2-aminoethane919797-21-02,5-dimethoxy-4-iodoH2-fluorophenyl
25I-NBBrN--1--2-aminoethane1648649-98-22,5-dimethoxy-4-iodoH2-bromophenyl
25I-NBTFMN--1--2-aminoethane2,5-dimethoxy-4-iodoH2-phenyl
25I-NBMDN--1--2-aminoethane919797-25-42,5-dimethoxy-4-iodoH2,3-methylenedioxyphenyl
25B-NBMDN--1--2-aminoethane1354632-19-12,5-dimethoxy-4-bromoH2,3-methylenedioxyphenyl
25C-NBMDN--1--2-aminoethane1373879-26-52,5-dimethoxy-4-chloroH2,3-methylenedioxyphenyl
25D-NBMDN--1--2-aminoethane1391488-97-32,5-dimethoxy-4-methylH2,3-methylenedioxyphenyl
25I-NBOHN--1--2-aminoethane919797-20-92,5-dimethoxy-4-iodoH2-hydroxyphenyl
25I-NBOMeN--1--2-aminoethane919797-19-62,5-dimethoxy-4-iodoH2-methoxyphenyl
DOI-NBOMeN--1--2-aminopropane2,5-dimethoxy-4-iodomethyl2-methoxyphenyl
25I-NBMeOHN--1--2-aminoethane1391494-71-52,5-dimethoxy-4-iodoH2-phenyl
25I-NBAmN--1--2-aminoethane1391494-85-12,5-dimethoxy-4-iodoH2-phenyl
25I-NMe7DHBFN--1--2-aminoethane2,5-dimethoxy-4-iodoH2,3-dihydrobenzofuran-7-yl
25I-N2Nap1OHN--1--2-aminoethane2,5-dimethoxy-4-iodoH1-hydroxynaphthalen-2-yl
25I-N3MT2MN--1--2-aminoethane1354632-66-82,5-dimethoxy-4-iodoH3-methoxythiophen-2-yl
25I-N4MT3MN--1--2-aminoethane1354632-73-72,5-dimethoxy-4-iodoH4-methoxythiophen-3-yl
25iP-NBOMeN--1--2-aminoethane1391487-83-42,5-dimethoxy-4-isopropylH2-methoxyphenyl
25N-NBOMeN--1--2-aminoethane1354632-03-32,5-dimethoxy-4-nitroH2-methoxyphenyl
25P-NBOMeN--1--2-aminoethane1391489-07-82,5-dimethoxy-4-propylH2-methoxyphenyl
25P-NBOHN--1--2-aminoethane1391490-34-82,5-dimethoxy-4-propylH2-hydroxyphenyl
25TFM-NBOMeN--1--2-aminoethane1027161-33-62,5-dimethoxy-4-H2-methoxyphenyl
25T-NBOMeN--1--2-aminoethane1539266-47-12,5-dimethoxy-4-H2-methoxyphenyl
25T2-NBOMeN--1--2-aminoethane2,5-dimethoxy-4-H2-methoxyphenyl
25T4-NBOMeN--1--2-aminoethane1354632-17-92,5-dimethoxy-4-H2-methoxyphenyl
25T7-NBOMeN--1--2-aminoethane1539266-55-12,5-dimethoxy-4-H2-methoxyphenyl
25T7-NBOHN--1--2-aminoethane1354632-41-92,5-dimethoxy-4-H2-hydroxyphenyl
NBOMe-mescalineN--1--2-aminoethane1354632-01-13,4,5-trimethoxyH2-methoxyphenyl
NBOMe-escalineN--1--2-aminoethane3,5-dimethoxy-4-ethoxyH2-methoxyphenyl
MDPEA-NBOMeN--1--2-aminoethane3,4-methylenedioxyH2-methoxyphenyl
MDBZN-benzyl-1--2-aminopropane65033-29-63,4-methylenedioxymethylphenyl
ClobenzorexN--1-phenyl-2-aminopropane13364-32-4Hmethyl2-chlorophenyl
4-EA-NBOMeN--1--2-aminopropane4-ethylmethyl2-methoxyphenyl
5-APB-NBOMeN--1--2-aminopropanebenzofuran-5-yl instead of phenylmethyl2-methoxyphenyl

Similar compounds with related structures are also known including;
Chemical structureCommon nameChemical nameCAS number
25B-N1POMeN--2,5-dimethoxy-4-bromophenethylamine1335331-49-1
1335331-51-5
2C-B-AN2-phenyl-2-acetonitrile
2CBCB-NBOMeN--1-methanamine1354634-09-5
2CBFly-NBOMeN--1--2-aminoethane1335331-42-4
2C-B-DRAGONFLY-NBOHN--1--2-aminoethane1335331-45-7
2C-B-FLY-NB2EtO5ClN--1--2-aminoethane
DMBMPP-2--6-piperidine1391499-52-7
25B-NAcPip2--1-ethanone
RH-343--1H-quinazoline-2,4-dione1028307-48-3
5MT-NBOMeN--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 or are otherwise covered by the Psychoactive Substances Act 2016.