2CB-Ind

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 ;
PubChem CID	16086368;
ChemSpider	17245022 ;
UNII	ZMP92SN5X2;
ChEMBL	ChEMBL424890 ;
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 ; Key:HCLPGYNQMVSQIM-UHFFFAOYSA-N ;
	(what is this?)

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]

Analogues and derivatives[]

Analogues and derivatives of 2C-B:

:

25-NB:

25B-NB
25B-NBF
25B-NBOH
25B-NBOMe (NBOMe-2CB)

:

Substituted benzofurans:

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

Other:

2C-B-BUTTERFLY
2CB-Ind
βk-2C-B (beta-keto 2C-B)
N-Ethyl-2C-B
TCB-2 (2C-BCB)

References[]

^ 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.
^ Braden MR (2007). Towards a biophysical understanding of hallucinogen action (PhD.). Purdue University. ProQuest 304838368.

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[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.

[1]

[2]

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?)

2CB-Ind

Analogues and derivatives[]

See also[]

References[]