2CB-Ind

2CB-Ind is a conformationally-restricted derivative of the phenethylamine hallucinogen 2C-B, discovered in 1974 by Alexander Shulgin. It acts as a moderately potent and selective agonist for the 5-HT_2A and 5-HT_2C receptors, but unlike the corresponding benzocyclobutene derivative TCB-2 which is considerably more potent than the parent compound 2C-B, 2CB-Ind is several times weaker, with racemic 2CB-Ind having a K_i of 47nM at the human 5-HT_2A receptor, only slightly more potent than the mescaline analogue (R)-jimscaline.^[1][2]

2CB-Ind

Clinical data
Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: uncontrolled
Identifiers
IUPAC name (5-bromo-4,7-dimethoxy-2,3-dihydro-1H-inden-1-yl)methanamine
CAS Number	912342-23-5 N
PubChem CID	16086368
ChemSpider	17245022 Y
UNII	ZMP92SN5X2
ChEMBL	ChEMBL424890 Y
CompTox Dashboard (EPA)	DTXSID70582080
Chemical and physical data
Formula	C12H16BrNO2
Molar mass	286.169 g·mol−1
3D model (JSmol)	Interactive image
SMILES COc1c(Br)cc(OC)c2c1CCC2CN
InChI InChI=1S/C12H16BrNO2/c1-15-10-5-9(13)12(16-2)8-4-3-7(6-14)11(8)10/h5,7H,3-4,6,14H2,1-2H3 Y Key:HCLPGYNQMVSQIM-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Analogues and derivatives

Analogues and derivatives of 2C-B:

25-N:

• 25B-N1POMe
• 25B-NAcPip

25-NB:

• 25B-NB
• 25B-NB23DM
• 25B-NB25DM
• 25B-NB3OMe
• 25B-NB4OMe
• 25B-NBF
• 25B-NBMD
• 25B-NBOH
• 25B-NBOMe (NBOMe-2CB)
  • DMBMPP

25-NM:

• 25B-NMe7BF
• 25B-NMe7BT
• 25B-NMe7Bim
• 25B-NMe7Box
• 25B-NMe7DHBF
• 25B-NMe7Ind
• 25B-NMe7Indz
• 25B-NMePyr

Substituted benzofurans:

• 2C-B-FLY
  • 2C-B-BUTTERFLY
  • 2C-B-DRAGONFLY
• 2CBFly-NBOMe (NBOMe-2CB-Fly)
• DOB-FLY
• DOB-2-DRAGONFLY-5-BUTTERFLY

N-(2C)-fentanyl:

• N-(2C-B) fentanyl^[3]
  • N-(2C-B-FLY) fentanyl^[4]

Other:

• BOB
• BOH-2C-B, β-Hydroxy-2C-B, βOH-2CB^[5][6]
• BMB
• 2C-B-5-hemifly
• 2C-B-aminorex (2C-B-AR)
• 2C-B-AN
• 2C-B-BZP
• 2C-B-FLY-NB2EtO5Cl
• 2C-B-PP
• 2CB-Ind
• βk-2C-B (beta-keto 2C-B)
• N-Ethyl-2C-B
• TCB-2 (2C-BCB)

See also

• AMMI

References

1. McLean TH, Parrish JC, Braden MR, Marona-Lewicka D, Gallardo-Godoy A, Nichols DE (September 2006). "1-Aminomethylbenzocycloalkanes: conformationally restricted hallucinogenic phenethylamine analogues as functionally selective 5-HT2A receptor agonists". Journal of Medicinal Chemistry. 49 (19): 5794–803. CiteSeerX 10.1.1.688.9849. doi:10.1021/jm060656o. PMID 16970404.
2. Braden MR (2007). Towards a biophysical understanding of hallucinogen action (PhD.). Purdue University. ProQuest 304838368.
3. "Explore N-(2C-B)-Fentanyl | PiHKAL · info". isomerdesign.com.
4. "Explore N-(2C-FLY)-Fentanyl | PiHKAL · info". isomerdesign.com.
5. Glennon, Richard A.; Bondarev, Mikhail L.; Khorana, Nantaka; Young, Richard; May, Jesse A.; Hellberg, Mark R.; McLaughlin, Marsha A.; Sharif, Najam A. (November 2004). "β-Oxygenated Analogues of the 5-HT2ASerotonin Receptor Agonist 1-(4-Bromo-2,5-dimethoxyphenyl)-2-aminopropane". Journal of Medicinal Chemistry. 47 (24): 6034–6041. doi:10.1021/jm040082s. ISSN 0022-2623. PMID 15537358.
6. Beta-hydroxyphenylalkylamines and their use for treating glaucoma