Chemistry:2CB-Ind

Short description: Chemical compound

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
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)

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.

Analogues and derivatives

Analogues and derivatives of 2C-B:

25-NB:

• 25B-NB3OMe
• 25B-NB4OMe
• 25B-NBF
• 25B-NBMD
• 25B-NBOH
• 25B-NBOMe (NBOMe-2CB)

Substituted benzofurans:

• 2C-B-FLY
• 2CBFly-NBOMe (NBOMe-2CB-Fly)

Other:

• 2C-B-AN
• 2C-B-BUTTERFLY
• 2C-B-DragonFLY
• 2CB-5-hemifly
• 2CB-Ind
• βk-2C-B (beta-keto 2C-B)
• TCB-2 (2C-BCB)

See also

• AMMI