2CLisaB
2CLisaB, also known as 2-[2-(4-bromo-2,5-dimethoxyphenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline, is a serotonin receptor modulator of the phenethylamine, 2C, and N-benzylphenethylamine families. It is a cyclized phenethylamine analogue of the serotonergic psychedelic 25B-NBOMe in which the N-benzyl group has been cyclized with the amine to form a tetrahydroisoquinoline ring. The drug shows affinity for the serotonin 5-HT2A and 5-HT2C receptors (Ki = 45–1,580 nM and 270–77,680 nM, respectively). 2CLisaB was first described in the scientific literature by Michael Robert Braden of the lab of David E. Nichols at Purdue University in 2007.
@media screen{html.skin-theme-clientpref-night .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa);color:inherit}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa);color:inherit}}
.mw-parser-output .infobox-subbox{padding:0;border:none;margin:-3px;width:auto;min-width:100%;font-size:100%;clear:none;float:none;background-color:transparent;color:inherit}.mw-parser-output .infobox-3cols-child{margin:-3px}.mw-parser-output .infobox .navbar{font-size:100%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .infobox-full-data:not(.notheme)>div:not(.notheme)[style]{background:#1f1f23!important;color:#f8f9fa}}@media(min-width:640px){body.skin--responsive .mw-parser-output .infobox-table{display:table!important}body.skin--responsive .mw-parser-output .infobox-table>caption{display:table-caption!important}body.skin--responsive .mw-parser-output .infobox-table>tbody{display:table-row-group}body.skin--responsive .mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}
| Column 1 |
|---|
| Serotonin receptor modulator |
| .mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}None |
| IUPAC name |
| 2-[2-(4-bromo-2,5-dimethoxyphenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline |
| C19H22BrNO2 |
| 376.294 g·mol−1 |
| Interactive image |
| SMILES |
| COc1cc(Br)c(cc1CCN1CCc2c(C1)cccc2)OC |
| InChI |
| InChI=1S/C19H22BrNO2/c1-22-18-12-17(20)19(23-2)11-15(18)8-10-21-9-7-14-5-3-4-6-16(14)13-21/h3-6,11-12H,7-10,13H2,1-2H3Key:FUQOBJZWVZVGDO-UHFFFAOYSA-N |
2CLisaB, also known as 2-[2-(4-bromo-2,5-dimethoxyphenyl)ethyl]-1,2,3,4-tetrahydroisoquinoline, is a serotonin receptor modulator of the phenethylamine, 2C, and N-benzylphenethylamine families. It is a cyclized phenethylamine analogue of the serotonergic psychedelic 25B-NBOMe in which the N-benzyl group has been cyclized with the amine to form a tetrahydroisoquinoline ring. The drug shows affinity for the serotonin 5-HT2A and 5-HT2C receptors (Ki = 45–1,580 nM and 270–77,680 nM, respectively). 2CLisaB was first described in the scientific literature by Michael Robert Braden of the lab of David E. Nichols at Purdue University in 2007.
The compound without the 4-bromo substitution is known as 2CLisaH. It shows much lower affinities for the serotonin 5-HT2A and 5-HT2C receptors (Ki = 690–1,158 nM and 1,303–1,404 nM, respectively).
- Substituted methoxyphenethylamine
- Cyclized phenethylamine
- 25-NB
- 2CBecca
- 2CJP
- 2C-B-3PIP-NBOMe
- 2C-B-3PIP-POMe
.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}body.skin-vector-2022 .mw-parser-output .reflist-columns-2{column-width:27em}body.skin-vector-2022 .mw-parser-output .reflist-columns-3{column-width:22.5em}.mw-parser-output .references[data-mw-group=upper-alpha]{list-style-type:upper-alpha}.mw-parser-output .references[data-mw-group=upper-roman]{list-style-type:upper-roman}.mw-parser-output .references[data-mw-group=lower-alpha]{list-style-type:lower-alpha}.mw-parser-output .references[data-mw-group=lower-greek]{list-style-type:lower-greek}.mw-parser-output .references[data-mw-group=lower-roman]{list-style-type:lower-roman}.mw-parser-output div.reflist-liststyle-upper-alpha .references{list-style-type:upper-alpha}.mw-parser-output div.reflist-liststyle-upper-roman .references{list-style-type:upper-roman}.mw-parser-output div.reflist-liststyle-lower-alpha .references{list-style-type:lower-alpha}.mw-parser-output div.reflist-liststyle-lower-greek .references{list-style-type:lower-greek}.mw-parser-output div.reflist-liststyle-lower-roman .references{list-style-type:lower-roman}
- 2CLisaB - Isomer Design
.mw-parser-output .asbox{position:relative;overflow:hidden}.mw-parser-output .asbox table{background:transparent}.mw-parser-output .asbox p{margin:0}.mw-parser-output .asbox p+p{margin-top:0.25em}.mw-parser-output .asbox-body{font-style:italic}.mw-parser-output .asbox-note{font-size:smaller}.mw-parser-output .asbox .navbar{position:absolute;top:-0.75em;right:1em;display:none}.mw-parser-output :not(p):not(.asbox)+style+.asbox,.mw-parser-output :not(p):not(.asbox)+link+.asbox{margin-top:3em}